Chicago
Browse by Month
Jump to any month from now through next summer — each one gets a can't-miss pick up top.
Every event is independently sourced — a few carry a ⚠ flag where a source disagreed on a date or venue; check the linked source before planning around those.
Sep13
Festivals & Street Fairs
Maxwell Street Market
Maxwell St. (Halsted to Union) · Near West Side / University Village
Free
Century-old open-air market — crafts, resale goods, food, live music. Recurring on select Sundays.
Sep26
Festivals & Street Fairs
Hyde Park Jazz Festival
Midway Plaisance, Logan Center, Smart Museum, Rockefeller Chapel · Hyde Park
Free ($10 suggested donation)
Free jazz festival across 30+ sets and multiple indoor/outdoor Hyde Park venues.
Sep25
Festivals & Street Fairs
World Music Festival Chicago
Chicago Cultural Center, Millennium Park, Navy Pier, Old Town School, Nat'l Museum of Mexican Art, Logan Center, Pritzker Pavilion · Citywide
Free
Free citywide festival with 30+ global artists/ensembles from 22 countries.
Oct11
Festivals & Street Fairs
Bank of America Chicago Marathon
Course through 29 neighborhoods, finish in Grant Park · Citywide / Loop finish
Free to spectate
48th running — ~50,000 runners; free to watch along the route or at the Grant Park finish.
Oct17
Festivals & Street Fairs
Open House Chicago
170+ sites across 20+ neighborhoods · Citywide
Free
Free citywide festival offering behind-the-scenes access to architecturally/historically significant buildings.
Festivals & Street Fairs
Neighborhood Farmers Markets (recurring)
Daley Plaza; Jarvis Square; Andersonville; SOAR Streeterville · Loop / Rogers Park / Andersonville / Streeterville
Free
Recurring weekly farmers markets across four neighborhoods through late October.
⚠ Recurring series, not a single date.
Sep26
Festivals & Street Fairs
Randolph Street Market
1341 W. Randolph St. · West Loop
$14 online/$15 door ($5–10 discounts)
European-style outdoor antique/vintage market, 300+ vendors, plus a food truck lineup.
Oct2
Festivals & Street Fairs
Lincoln Square Ravenswood Apple Fest
N. Lincoln Ave (Sunnyside to Lawrence) · Lincoln Square
$5 suggested donation
39th annual — fall harvest street fest, apple-themed food and goods, live music, family activities.
Sep4
Food & Drink
Chi Food Truck Fest (weekly)
Daley Plaza · Loop
Free entry (pay per item)
City-run weekly food truck rally, lineup announced weekly via @ChicagoBACP.
Sep25
Food & Drink
St. Alphonsus Oktoberfest (25th Annual)
1429 W Wellington Ave · Lakeview
$10 Fri/Sat; $5 suggested donation Sun
Bavarian beer-hall street fest — oompah bands, stein-holding, Sunday Kinderfest for kids.
Oct10
Food & Drink
Oktoberfestiversary (Dovetail x Begyle)
Shared lot, Dovetail Brewery & Begyle Brewing · North Center
$5 suggested donation (benefits food pantry)
Annual fall beer celebration marking Begyle's anniversary — special tappings, live music, food trucks.
Sep24
Food & Drink
Chicago Gourmet 2026
Millennium Park (Harris Theater Rooftop & Pritzker Pavilion) · Loop
Varies by sub-event, $115–$255
Chicago's premier culinary festival with national/local chefs; umbrella event for the four tastings below.
Sep26
Food & Drink
All You Can Eataly: Septemberfest
Eataly Chicago · River North
GA $150.99; VIP $210.01
All-you-can-eat/drink Italian night — 30+ chef-curated food stations, 15 drink stations, Second City comedy.
⚠ One source listed Sept 18 — confirmed date is Sept 26 per Eventbrite/Eataly.
Sep24
Food & Drink
Chicago Gourmet — Tacos & Tequila
Millennium Park (Chicago Gourmet grounds) · Loop
Not listed
Gourmet tacos paired with premium tequila/mezcal, hosted by Rick Bayless, Marcos Carbajal, Diana Dávila; mariachi and dancers.
Sep25
Food & Drink
Chicago Gourmet — Hamburger Hop
Millennium Park (Chicago Gourmet grounds) · Loop
Not listed
Chefs Joe Flamm and Jeff Mauro host a burger tasting/voting competition paired with beer and cocktails.
Sep26
Food & Drink
Chicago Gourmet — Grand Cru
Harris Theater Rooftop / Pritzker Pavilion · Loop
Not listed
Wine/cocktail/cuisine tasting with chefs Stephanie Izard, Lee Anne Wong, Sarah Grueneberg, Chris Shepherd, plus live chef demos.
Sep27
Food & Drink
Chicago Gourmet — Rise & Shine Gourmet
Millennium Park (Chicago Gourmet grounds) · Loop
Not listed
Southern-style brunch hosted by Erick Williams and Art Smith.
Sep17
Food & Drink
Fulton Market Oktoberfest (Oktoberfest Nation)
171 N Peoria St · Fulton Market / West Loop
Ticketed, price TBD
Chicago's largest outdoor Oktoberfest — imported Hofbräu München beer, pretzels, bratwurst, live German music; six-week run.
Sep18
Food & Drink
Oktoberfest at The Northman Beer & Cider Garden
233 E Riverwalk · Loop / Riverwalk
Not listed
Three-weekend riverside Oktoberfest — pretzels, German sausages, beer steins, polka music.
Sep25
Food & Drink
Jerk, Seafood & Vegan Fest (JSVFest) / African-Caribbean Int'l Festival
Union Park (per JSVFest listing) — one source says Washington Park · West Loop
Not listed
10th annual combined jerk/seafood/vegan food festival and Caribbean/African cultural festival with live music and vendors.
⚠ VENUE CONFLICT: sources disagree (Union Park vs Washington Park) — verify before publishing.
Sep26
Food & Drink
2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival
Downtown Chicago (exact address via ticket link) · Downtown
Not listed (limited to 299 guests)
Curated tasting of 20+ premium tequila/whiskey brands, expert-led; benefits Bear Necessities Pediatric Cancer Foundation.
Oct11
Food & Drink
Lincoln Park Wine Fest (10th Anniversary)
Jonquil Park · Lincoln Park
Not listed (21+ only)
10th-anniversary wine festival — tastings from numerous wineries, seminars, live music.
Oct18
Food & Drink
International Wine and Spirits Trade Show
Navy Pier · Streeterville
Not listed (trade-focused)
Trade-focused wine/spirits show on Italian wine in the US — blind tastings, industry panels.
Oct15
Food & Drink
Whisky Jewbilee Chicago 2026
Artifact Events · Ravenswood
Not listed
Whisky festival celebrating 15 years of Single Cask Nation — rare pours, kosher food, 21+.
Music & Nightlife
Second City Mainstage 114th Revue
The Second City · Old Town
From $74 (avg ~$86)
Flagship sketch/improv revue running continuously through the fall.
Sep25
Music & Nightlife
Polyphia Tour MMXXVI
Aragon Ballroom · Uptown
From $75 (avg ~$113)
Instrumental prog-rock band with RJ Pasin and Ladrones.
Oct3
Music & Nightlife
Brand New
Aragon Ballroom · Uptown
From $93 (Oct 4) / $124 (Oct 3)
Emo/rock band plays two consecutive nights.
Sep25
Music & Nightlife
Paula Cole & Rett Madison
Thalia Hall · Pilsen
Not listed
Singer-songwriter Paula Cole with opener Rett Madison.
Sep29
Music & Nightlife
Arlo Parks with Baird
Thalia Hall · Pilsen
Not listed
British singer-songwriter Arlo Parks with support from Baird.
Oct24
Music & Nightlife
Tank and the Bangas
Thalia Hall · Pilsen
Not listed
New Orleans genre-bending band headlines.
Oct29
Music & Nightlife
The Tallest Man On Earth with Gwenifer Raymond
Thalia Hall · Pilsen
Not listed
Swedish folk artist with opener Gwenifer Raymond.
Oct30
Music & Nightlife
Sanctum Dark Music Festival
Thalia Hall · Pilsen
Not listed
Two-night dark/goth/industrial music festival around Halloween.
Sep22
Music & Nightlife
wave to earth — the pieces tour
Aragon Ballroom · Uptown
Not listed
South Korean indie band's the pieces tour.
Oct13
Music & Nightlife
Jessie Ware: The Superbloom Tour
Aragon Ballroom · Uptown
Not listed
British pop/R&B singer's Superbloom Tour.
Oct4
Music & Nightlife
Bright Eyes with Lullaby for the Working Class
Metro · Wrigleyville
Not listed
Indie band Bright Eyes with support from Lullaby for the Working Class.
Sep25
Music & Nightlife
Cold Waves XIV
Metro · Wrigleyville
Single-day or 3-day pass
Annual industrial/darkwave festival — Stabbing Westward, Pig, Tr/st, King Woman and others.
Oct18
Music & Nightlife
Digable Planets – Blowout Comb 30th Anniversary Tour
Metro · Wrigleyville
Not listed
Classic hip-hop group's 30th-anniversary tour, Rich Robbins opening.
Oct22
Music & Nightlife
Whitney
Metro · Wrigleyville
Not listed
Chicago-born indie band, hometown show, Greg Mendez opening.
Oct3
Music & Nightlife
SERUM series
PRYSM · Fulton Market / West Loop
Not listed
Weekly October house/techno club series, rotating headliners incl. Dusky.
Sep22
Arts & Culture
teamLab: Everything Exists in Infinite Continuity
Smart Museum of Art · Hyde Park
Free
Oct15
Arts & Culture
FLEUROTICA
Garfield Park Conservatory · East Garfield Park
Not yet listed
A floral fashion show that's exactly as strange and wonderful as it sounds — Chicago florists, fashion designers, and students building runway-ready garments entirely out of flowers and plant material, under the Conservatory's own glass. Ticket price not published yet, but this benefit gala has become a genuine fall-calendar fixture for the city's design scene.
Sep25
Arts & Culture
Where Memory Lives: 40 Years of Día de Muertos
National Museum of Mexican Art · Pilsen
Free
40th annual Día de Muertos exhibition; includes community ofrenda.
Oct2
Arts & Culture
The Big Picture: Midwest Large Format Photography
Chicago Cultural Center · Loop
Free
Sep6
Arts & Culture
Mary Cassatt: After Impressionism
Art Institute of Chicago · Loop
$32 non-resident / $20 resident; members free
Cassatt's career following the final Impressionist group show of 1886.
Arts & Culture
Embroidered Traditions from Morocco to Afghanistan
Art Institute of Chicago · Loop
$32 non-resident / $20 resident; members free
The Art Institute's first-ever exhibition devoted entirely to SWANA (Southwest Asia and North Africa) textile traditions — 70+ pieces spanning the 18th through 20th centuries, most never shown publicly before. A genuinely different kind of show than the museum's usual European-painting anchors.
Arts & Culture
After the Age of Dinosaurs
Field Museum · Near South Side
$43 adult / $34 Chicago resident (All-Access Pass); members free
What actually took over once the asteroid hit — a 45-foot titanoboa, six-foot penguins, and touchable fossil casts of the weird mammals, birds, and reptiles that filled the post-dinosaur world. Chicago illustrator Jay Ryan made original screen-print art just for this one, a nice local touch on a show this big.
Arts & Culture
Paris in Black: Internationalism and the Black Renaissance
DuSable Black History Museum and Education Center · Hyde Park / Washington Park
$14.50 non-resident / $12.50 Chicago resident (free Wednesdays & first Friday monthly)
A real, specific story: Black American artists who left the U.S. for Paris between the 1890s and mid-20th century to escape racism at home and helped power the New Negro Movement from abroad. 100+ objects from The DuSable's own permanent collection, most rarely on public view. Free Wednesdays and the first Friday of the month make this an easy add to a Hyde Park museum day.
Oct24
Arts & Culture
Threads of a Nation
Chicago History Museum · Lincoln Park
$19 adult / $17 senior; children 6-12 free
Real, specific, goosebump-inducing artifacts, not generic period costume: the black velvet coat George Washington wore to his second inauguration, and the cape and bonnet Mary Todd Lincoln had on the night her husband was shot. The show is as much about the conservators who keep 200-year-old fabric from disintegrating as it is about the garments themselves.
Arts & Culture
Archivos Vivos
National Museum of Puerto Rican Arts and Culture · Humboldt Park
Free
Visual art, room-scale installation, and poetry woven together around a real question: what actually connects Puerto Rican identity across generations and geography once you're generations removed from the island. Housed in Humboldt Park's landmark former stables building, and like everything at this museum, admission is free.
Arts & Culture
Pink Floyd's The Dark Side of the Moon (Fulldome Show)
Adler Planetarium (Grainger Sky Theater) · Near South Side
$20 (plus museum admission)
Not a laser-light-show gimmick — a genuine 45-minute fulldome production built with the band's own involvement for the album's 50th anniversary, wrapping the full Dark Side of the Moon in cosmic visuals and surround sound under a real planetarium dome. Late Wednesday-night showtimes make it a real date-night option, not just a field-trip staple.
Family & Free Community
Shedd Aquarium: Immersion Theater 4D Experiences
Shedd Aquarium (Phelps Auditorium) · Near South Side
$5.95 add-on ($2.95 members)
A fully rebuilt theater with a screen that wraps along the side walls, plus wind, mist, and real scent effects synced to the film — genuinely different from a normal nature documentary. Three short films to choose from (penguins, sharks, octopuses), each an easy $5.95 add-on to a regular admission ticket rather than its own separate trip.
Nov7
Arts & Culture
Rashid Johnson: A Poem for Deep Thinkers
Museum of Contemporary Art Chicago · Near North Side
$22 adult / $14 student-senior; children free
Johnson's third solo show at the MCA, and his biggest one yet here — 70 works spanning two decades, including the black-soap-and-wax 'Cosmic Slops' reliefs and the black-and-white photos of the fictional New Negro Escapist Social and Athletic Club, riffing on W.E.B. Du Bois. A real museum-scale survey, not a single-room sampler.
Arts & Culture
Slow Dance
Museum of Contemporary Art Chicago · Near North Side
$22 adult / $14 student-senior; children free
Not a dance show in the spectacular sense — a group exhibition (Brendan Fernandes, Gordon Hall, Geumhyung Jeong, Carolyn Lazard, Melanie McLain, Cally Spooner) asking what happens to a body when it slows down, pauses, or refuses to perform on demand. A genuinely different register than a typical painting-and-sculpture show.
Oct24
Music & Nightlife
MAHLER X NOTORIOUS B.I.G. X 2PAC
Harris Theater · Loop
From $38
Composer-conductor Steve Hackman weaves Mahler's Resurrection Symphony together with Biggie and Tupac's biggest tracks — 'Juicy,' 'California Love,' 'Hypnotize' — performed live by a full orchestra. Sounds like a novelty on paper; audiences elsewhere have called it one of the most genuinely moving concert experiences they've had.
Nov14
Arts & Culture
Sol Invictus (Compagnie Hervé Koubi)
Harris Theater · Loop
From $57
A Chicago debut for choreographer Hervé Koubi's company, blending contemporary dance, hip hop, and capoeira and other martial arts into a single, physically ferocious piece named for Rome's 'invincible sun' deity. Not ballet, not breakdancing — genuinely its own thing.
Oct9
Arts & Culture
Emma Stebbins: Carving Out History
Driehaus Museum · Near North Side
$23 adult / $18 senior / $13 student; children 12 & under free
The first major museum look at Stebbins, one of the most significant American sculptors of the 19th century and among the first women to work at that scale professionally — best known for the Bethesda Fountain angel in Central Park, a piece most visitors have stood under without knowing who made it.
Dec10
Arts & Culture
Impressive Textiles: Printing on Fabric
Newberry Library · Near North Side
Free
A genuinely obscure corner of print history — five centuries of images, books, and maps printed on cloth instead of paper, from luxury satin state portraits to satirical cotton handkerchiefs, tracing back to devotional images tied to the Shroud of Turin. Like everything at the Newberry, free with no advance registration.
Arts & Culture
The Artistry of Plastic Surgery
International Museum of Surgical Science · Gold Coast
$25 adult / $18 senior-student-military
A yearlong series of rotating monthly exhibitions pairing surgical pioneers with contemporary artists around one real idea: surgeons and sculptors both spend their careers shaping the human form, just with different tools. Includes real, sobering history — how WWI and WWII surgeons had to become artists to reconstruct faces destroyed by combat. One of the odder, more memorable museum stops in the city.
Jun10
Arts & Culture
Say It with Pictures: Photography, Black Chicago and the Great Migration
Newberry Library · Near North Side
Free
A real, specific local story: how Black Chicagoans arriving during the Great Migration used photography — studio portraits, family albums, photojournalism — to document their own lives on their own terms, not as subjects of someone else's lens. Free, like every Newberry show.
Mar11
Arts & Culture
Metal, Paper, Ink: Early Printing from Jikji to Gutenberg
Newberry Library · Near North Side
Free
The real, less-Eurocentric version of print history: Korea's Jikji, printed with movable metal type in 1377, seven decades before Gutenberg's Bible. A genuinely global reframing of a story most people only ever hear the German half of.
Feb28
Arts & Culture
Zurbarán: Divine Light
Art Institute of Chicago · Loop
$32 non-resident / $20 resident; members free
A rare full showcase for the Spanish Golden Age painter best known for stark, almost sculptural saints and still lifes — the kind of show that doesn't tour to many U.S. cities. A slow-burn recommendation for anyone who finds the museum's Impressionist wing crowded and wants a quieter room.
Sep11
Arts & Culture
Karimah Ashadu: Machine Boys
Art Institute of Chicago · Loop
Included with general admission
Video installation.
Sep19
Arts & Culture
Jill Mulleady: The Passenger
Art Institute of Chicago · Loop
Included with general admission
Sep23
Arts & Culture
Utamaro: Elements of Beauty
Art Institute of Chicago · Loop
Included with general admission
Oct3
Arts & Culture
Tony Cokes: On Boredom
Art Institute of Chicago · Loop
Included with general admission
Sep17
Arts & Culture
Liliom (Chicago Premiere)
Lyric Opera House · Loop
From $47
Joffrey Ballet's Chicago premiere of John Neumeier's narrative ballet, score by Michel Legrand.
Sep17
Arts & Culture
Topdog/Underdog
Steppenwolf Theatre · Lincoln Park
Not listed
Suzan-Lori Parks' Pulitzer-winning drama, directed by Kenny Leon.
Oct22
Arts & Culture
Adirondack Chair Circle
Steppenwolf Theatre (Ensemble Theater) · Lincoln Park
Not listed
Stephanie Alison Walker's world-premiere comedy.
Sep5
Arts & Culture
The Attic
Goodman Theatre, Albert Theatre · Loop
Not listed
Circus-infused theater piece written/directed/choreographed by Shana Carroll (The 7 Fingers).
Sep26
Arts & Culture
Dead Girl's Quinceañera
Goodman Theatre, Owen Theatre · Loop
Not listed
By Phanésia Pharel, directed by Melia Bensussen.
Sep11
Arts & Culture
Play On!
Chicago Shakespeare Theater · Navy Pier / Streeterville
Not listed
Musical inspired by Twelfth Night set to Duke Ellington's music.
Sep10
Arts & Culture
The Humanities
Victory Gardens Theater at Biograph Theatre · Lincoln Park
Not listed
World premiere of Zayd Ayers Dohrn's play, directed by Eddie Torres, cast incl. Nora Dunn.
Oct18
Arts & Culture
Come From Away
Marriott Theatre · Lincolnshire, IL
Not listed
Musical run continuing through mid-October.
Oct18
Arts & Culture
Buddy – The Buddy Holly Story
Drury Lane Theatre · Oakbrook Terrace, IL
Not listed
Musical run continuing through mid-October.
Oct9
Arts & Culture
Escape to Margaritaville
Music Theater Works, North Shore Center for the Performing Arts · Skokie, IL
Not listed
Jimmy Buffett jukebox musical.
Sep25
Arts & Culture
Inner Worlds: Visions from the Hirshhorn Collection
Wrightwood 659 · Lincoln Park
Not listed (advance reservation required)
Yayoi Kusama Infinity Mirror Rooms + pumpkin sculpture, Mary Bauermeister, Niki de Saint Phalle works.
Sep23
Arts & Culture
Filter Photo Festival (18th annual)
Columbia College Chicago Student Center; Filter Space gallery · Downtown / West Town
Not listed (registration-based)
Photography festival with workshops and exhibitions.
Oct14
Arts & Culture
62nd Chicago International Film Festival
Multiple venues; HQ at 212 W Van Buren St · Citywide
Not listed (early-bird passes)
North America's longest-running competitive film festival; 150+ international films.
Oct30
Arts & Culture
Family Field Nights: Boo with SUE
Field Museum · Near South Side
Not listed
Museum after-hours family event.
Sep26
Sports
Blackhawks Preseason vs. St. Louis Blues
United Center · Near West Side
$20 (200 level) / $30 (100 level)
Blackhawks preseason home game vs. St. Louis Blues.
Sep28
Sports
Bears vs. Philadelphia Eagles
Soldier Field · Near South Side
Not listed
Monday Night Football — Bears host the Eagles.
Oct4
Sports
Bears vs. New York Jets
Soldier Field · Near South Side
Not listed
Bears home game vs. the Jets.
Oct22
Sports
Bears vs. New England Patriots
Soldier Field · Near South Side
Not listed
Thursday Night Football — Bears host the Patriots.
Oct7
Sports
Bulls Preseason vs. Phoenix Suns
United Center · Near West Side
Not listed
Bulls preseason home opener vs. Phoenix Suns.
Oct9
Sports
Bulls Preseason vs. Memphis Grizzlies
United Center · Near West Side
Not listed
Bulls preseason home game vs. Memphis Grizzlies.
Oct16
Sports
Bulls Preseason vs. Minnesota Timberwolves
United Center · Near West Side
Not listed
Bulls preseason home game vs. Minnesota Timberwolves.
Oct24
Sports
Bulls Regular-Season Home Opener vs. Washington Wizards
United Center · Near West Side
Not listed
Home opener, and a real rookie storyline to watch for it: the Bulls' Caleb Wilson against the Wizards' No. 1 overall pick, AJ Dybantsa. Date's now confirmed — no more hedging on this one.
Oct4
Sports
Chicago Fire FC vs. Inter Miami CF
Soldier Field · Near South Side
From $148
The single biggest home draw on the Fire's entire schedule — Lionel Messi's team, and by a wide margin the most expensive ticket of the Fire's season on the resale market. Parking lots open at 3:30 PM, worth building in extra time given how this one draws compared to a normal MLS Tuesday.
Oct6
Sports
Chicago Fire FC vs. Vancouver Whitecaps
Soldier Field · Near South Side
From $42
Originally a July date that got postponed and slotted back in for October — the Whitecaps have quietly been one of the West's better sides, so this makeup match carries more stakes than a typical rescheduled midweek game.
Oct10
Sports
Chicago Fire FC vs. New York City FC
Soldier Field · Near South Side
Not listed
A Saturday-afternoon date rather than the usual weeknight kickoff, which makes it the easiest Fire home game all month to actually plan a full day around. Naruto shirt giveaway to the first 5,000 fans through the gate, a genuinely odd but real promotion.
Oct14
Sports
Chicago Fire FC vs. Philadelphia Union
Soldier Field · Near South Side
Not listed
A midweek night match under the lights at Soldier Field — smaller crowd than a Saturday date, easier to grab a last-minute ticket if you're deciding same-day.
Oct28
Sports
Chicago Fire FC vs. Orlando City SC
Soldier Field · Near South Side
From $38
A 2025 MLS Cup Playoff opponent visits with the regular season winding down, one of the Fire's last home dates before the schedule flips to the postseason picture. Stein giveaway to the first 5,000 fans through the gate.
Sep24
Family & Free Community
Go Run Chicago (free 5K/1-mile series)
Rotates: Humboldt Park, Warren Park, Washington Park · Humboldt Park / Rogers Park / Washington Park
Free (registration required)
Weekly free timed 5K/1-mile run-walk series, all skill levels, via Chicago Park District.
Oct2
Family & Free Community
West Town Art Walk
Multiple galleries/businesses, West Town · West Town
Free
Free neighborhood art walk with food and shopping.
⚠ 2026 exact dates unconfirmed — based on prior-year pattern.
Sep25
Family & Free Community
Fall Fest at Lincoln Park Zoo
Lincoln Park Zoo · Lincoln Park
Free admission; ticketed add-ons (slide, Ferris wheel, bounce house)
Free family fall festival — pumpkin patch, pumpkin carvers, live music, animal enrichment.
Oct24
Halloween & Fall Seasonal
Arts in the Dark Halloween Parade
Columbus Drive · Loop / Grant Park area
Free
12th annual nighttime Halloween parade — giant puppets, floats, and performances stepping off from Balbo Drive and marching north, expected to draw over 100,000 spectators. The earlier 'Oct 18' rumor didn't hold up; two independent sources now confirm Oct 24.
Sep12
Halloween & Fall Seasonal
Richardson Adventure Farm: World's Largest Corn Maze
Richardson Adventure Farm · Spring Grove
From $22
This isn't a hyperbole-branding thing — it's a real 9-10 mile trail cut through 28 acres of live corn. 2026's design marks the country's 250th anniversary. The two corn mazes already on this page (Goebbert's, Jack's Pumpkin Pop-Up) are convenient; this one is the actual big one worth the drive to Lake County for.
Oct31
Halloween & Fall Seasonal
Northalsted Halloween Parade (Haunted Halsted)
Halsted St (Aldine to Addison) · Lakeview / Northalsted
Free to watch
Costume parade and block party, plus costume contest after.
Oct31
Halloween & Fall Seasonal
Slightly Spooky Saturday
Navy Pier · Streeterville
Free (general Navy Pier admission)
Family Halloween celebration — trick-or-treating, performances, workshops.
Oct3
Halloween & Fall Seasonal
Boo! at the Zoo
Brookfield Zoo Chicago · Brookfield, IL (western suburb)
Included with zoo admission; free for members
Halloween-themed zoo event — trick-or-treating, inflatables, costume parades.
⚠ Located in Brookfield, a western suburb, not the city proper.
Oct18
Halloween & Fall Seasonal
Spooky Zoo
Lincoln Park Zoo · Lincoln Park
Free
Daytime Halloween event — trick-or-treat for sustainable candy, storytelling, music, free carousel.
Oct7
Halloween & Fall Seasonal
Night of 1,000 Jack-o'-Lanterns
Chicago Botanic Garden · Glencoe, IL (North Shore suburb)
~$21–24.50 adult / ~$14–17.50 kids 3–12
Illuminated path of 1,000+ artist-carved pumpkins, live carving demos.
⚠ Located in Glencoe, a North Shore suburb, not the city proper.
Oct31
Halloween & Fall Seasonal
Gods of Chaos Halloween
Aragon Ballroom · Uptown
Not listed
Large-scale Halloween EDM/costume party.
Oct31
Halloween & Fall Seasonal
Nocturna: All Hallows' Eve Ball
Metro · Wrigleyville
Not listed
Goth/industrial Halloween dance party, DJ Scary Lady Sarah.
Oct24
Halloween & Fall Seasonal
Music Box of Horrors 2026
Music Box Theatre · Southport Corridor
Not listed (sells out fast)
24-hour horror movie marathon with special guests and vendors.
Nov20
Festivals & Street Fairs
Christkindlmarket Chicago at Daley Plaza
Daley Plaza (50 W. Washington St.) · Loop
Free admission
Chicago's original German Christmas market turns 30 this year — wooden chalets, mulled wine (Glühwein), ornaments, and food stalls filling the plaza.
Nov21
Family & Free Community
Wintrust Magnificent Mile Lights Festival
North Michigan Avenue (Oak St. to the Chicago River) · Streeterville / Magnificent Mile
Free
35th-anniversary holiday lights parade down Michigan Avenue led by Mickey and Minnie, capped by fireworks over the river.
Nov20
Family & Free Community
Lincoln Park ZooLights
Lincoln Park Zoo · Lincoln Park
$7–10; free on select Mondays (tickets still required)
30th-anniversary holiday lights display — 3+ million lights across the zoo grounds. Closed Thanksgiving, Christmas Eve and Day, and a few December Tuesdays, but open both New Year's Eve and Day.
Nov26
Family & Free Community
Chicago Thanksgiving Parade
State Street (Ida B. Wells Dr. to Randolph St.) · Loop
Free
Chicago's actual Thanksgiving-morning tradition, 92 years running now — floats and marching bands up State Street before anyone's carved anything. Free, obviously, and it draws the kind of crowd that means showing up an hour early isn't optional if you want to see anything past someone's shoulder.
Dec31
Family & Free Community
Navy Pier New Year's Eve Fireworks
Navy Pier · Streeterville
Free
Ten minutes, midnight, over the lake — free and synchronized to music, which sounds like a small thing until you're actually standing on the pier and the timing lands. The city runs a second show over the river downtown at the same moment, so pick a side rather than trying to see both.
Nov27
Family & Free Community
Wintrust Winter WonderFest
Navy Pier (Festival Hall) · Streeterville
$27 advance / $32 at door; kids 2 & under free
Navy Pier's answer to a Midwest winter — an indoor amusement park under one roof, ice rink included with admission, expanded this year with more rides than the last few seasons. Not cheap at the door, but book ahead and it's noticeably less.
Food & Drink
Chicago Restaurant Week 2027
Citywide — participating restaurants · Citywide
Fixed-price menus, set per restaurant
The city's biggest organized excuse to try somewhere new — participating restaurants run fixed-price menus for just over two weeks, which is exactly the kind of deal this site exists to track. 2027 dates aren't out yet; last year ran Jan 23–Feb 8, so plan around that window until the official one drops.
⚠ Exact 2027 dates not yet announced — save-the-date based on last year's pattern, not confirmed. Recheck closer to January.
Feb13
Festivals & Street Fairs
Chicago Auto Show
McCormick Place · Near South Side
$20 adults / $15 seniors & kids 4–12; free under 3 (weekday & first-responder discounts available)
119 years running, North America's biggest auto show under one roof — every manufacturer's newest metal, EV test tracks, and actual new-car smell for nine straight days. Skip opening weekend if you'd like to see any of it without shuffling through a crowd.
Mar13
Festivals & Street Fairs
Chicago St. Patrick's Day Parade & River Dyeing
Columbus Drive (Balbo Dr. to Monroe St.); river dyeing near the Columbus Dr. bridge · Loop
Free
Two events, same morning: the river goes green first, then the parade steps off a couple hours later — one of the single biggest downtown crowds all year, and completely free. Claim a curb spot early if you actually want to see anything.
⚠ 2027 date is the expected pattern (Saturday nearest March 17), not yet officially confirmed by the city — recheck closer to March.
Nov22
Sports
Bears vs. New Orleans Saints
Soldier Field · Near South Side
Not listed
Nothing at stake in the standings on paper, but a late-November Sunday at Soldier Field doesn't need playoff implications to be worth the trip — dress like it, lakefront wind doesn't care about the score.
Dec6
Sports
Bears vs. Jacksonville Jaguars
Soldier Field · Near South Side
Not listed
A December Soldier Field game means one thing regardless of opponent: layers. Early-slate Sunday, so build the tailgate around a noon kickoff, not an afternoon one.
Dec25
Sports
Bears vs. Green Bay Packers (Christmas Day)
Soldier Field · Near South Side
Not listed
The rivalry that doesn't take holidays off — Bears-Packers on Christmas Day, kicking off Netflix's holiday doubleheader at noon. Whatever else Dec. 25 looks like this year, there's a real chance it ends at Soldier Field.
Oct6
Sports
Blackhawks Home Opener vs. St. Louis Blues
United Center · Near West Side
Not listed
A young, rebuilding roster still means a packed United Center on opening night — this fanbase shows up regardless of where the team is in the cycle. Central Division matchup to kick off the season.
Oct10
Sports
Blackhawks vs. Carolina Hurricanes
United Center · Near West Side
Not listed
The reigning Stanley Cup champs come to town four games into the Hawks' season — a real measuring-stick night, not just another Saturday on the schedule.
Nov17
Sports
Blackhawks vs. Toronto Maple Leafs
United Center · Near West Side
Not listed
Original Six matchup, and Leafs road games sell out on the strength of Toronto's own fanbase alone — expect a louder, more divided United Center than most nights on the schedule.
Nov13
Arts & Culture
A Christmas Carol
Goodman Theatre (Albert Theatre) · The Loop
From $25
Goodman's own holiday tradition, running continuously since 1978 — one of the longest-running productions of its kind in the country, not just a local talking point. Tim Hopper takes over as Scrooge this year inside the Albert Theatre, tucked into the old Reid Murdoch building. Tickets start at $25, which is a real bargain for a show this well-drilled, and sensory-friendly performances are built into the run for anyone who needs them.
Dec4
Arts & Culture
The Nutcracker (Joffrey Ballet)
Lyric Opera House · The Loop
$50–$171
Christopher Wheeldon's version swaps the usual German fairy tale for 1893 Chicago — Marie's dream sequence runs through the World's Columbian Exposition instead of a generic European court, which makes this the one Nutcracker that's actually about the city staging it. The run stretches over three weeks at the Lyric, so there's real flexibility on when to go instead of chasing a single sold-out weekend.
Nov13
Family & Free Community
Lightscape at Chicago Botanic Garden
Chicago Botanic Garden · Glencoe, IL (North Shore suburb)
Timed tickets, under $30 on off-peak dates — rises with demand
The Botanic Garden's answer to a Midwest winter: a 1.3-mile illuminated trail that gets a genuine overhaul most years instead of just switching the same lights back on. This one reworks more than 80% of the installations, including a newly redone stretch through Evening Island, for its eighth year running. Pricing moves with demand, so the cheaper nights — marked on the Garden's own calendar — are worth chasing if your date isn't fixed.
Mar25
Sports
Cubs Opening Day vs. Cleveland Guardians
Wrigley Field · Lakeview
Not listed
The earliest Opening Day in MLB history, and it's at Wrigley — a Thursday off work well spent if you can swing it. First home game of a season that's about to get a lot bigger, too (see the All-Star Game below).
Jul4
Sports
Cubs vs. St. Louis Cardinals (Independence Day)
Wrigley Field · Lakeview
From $144
The Cubs have now made this an actual tradition — hosting their oldest rival on July 4th for the second summer running. It's the finale of a 4-game set, and there's no more Chicago way to spend the holiday than bleachers, a hot dog, and the Cardinals in town.
Jul12
Sports
MLB Home Run Derby at Wrigley Field
Wrigley Field · Lakeview
Not listed — expect a lottery/travel-package system given the demand
The night before the main event — baseball's best power hitters, one of the sport's genuinely fun spectacles, and it's happening on Waveland Avenue's actual home turf for the first time in 37 years.
Jul13
Sports
2027 MLB All-Star Game at Wrigley Field
Wrigley Field · Lakeview
Not listed — expect a lottery/travel-package system given the demand
Wrigley's fourth All-Star Game, and its first since 1990 — a genuinely historic date for a genuinely historic ballpark, not a marketing line. If you only plan one thing around next summer, this is the one worth planning around.
Sep14
Arts & Culture
Chicago Humanities Festival — Fall 2026
Venues citywide · Citywide
Varies by event — many free, ticketed talks typically $10–$40
Real names, real ideas — a lineup that puts Kyle MacLachlan, Ira Glass, and Marlon James in the same season and nobody blinks. It runs city-wide for nearly two months, but the days actually worth building a schedule around are the all-day stops: Pilsen on Sept 26, Northwestern in Evanston on Oct 4, and Hyde Park on Nov 7, where you can stack several talks without driving anywhere in between.
Sep23
Family & Free Community
One Book, One Chicago 2026: Orbital
Chicago Public Library (all branches) · Citywide
Free
The whole city assigned the same novel at once, on purpose — this year's pick is Samantha Harvey's 'Orbital,' a slim, quietly devastating book about astronauts that somehow also won the Booker Prize. Free programming runs at libraries citywide through the fall, from a Silent Reading Soirée at Harold Washington on Sept 23 to a virtual author keynote closing things out Nov 19.
Dec19
Music & Nightlife
SantaCon Chicago
Starting bar TBA (downtown) · Loop/River North area
Varies — typically a small wristband fee plus bar prices
A few hundred strangers in cheap Santa suits, day-drinking their way across a rotating list of bars — exactly as chaotic and exactly as fun as that sounds. Check-in runs a loose four-hour window so nobody's actually starting or finishing together, which is honestly part of the appeal.
Arts & Culture
Chicago International Puppet Theater Festival
Fine Arts Building, Chicago Children's Theatre & other stages · Citywide
Varies by event
Not a kids'-table event — this pulls 25,000+ people a year for puppetry that ranges from genuinely avant-garde to just plain unsettling, spread across stages like the Fine Arts Building and Chicago Children's Theatre. 2027 dates aren't locked yet, but the last several years have landed in the back half of January, so pencil it in loosely until the festival confirms.
⚠ 2027 dates not yet officially announced — verify closer to the date.
Nov7
Family & Free Community
Christmas Around the World & Holidays of Light
Griffin Museum of Science and Industry · Hyde Park
Included with general admission ($25.95 adult / $14.95 child)
Fifty-plus trees, each one decorated by a different Chicago cultural or immigrant community group, filling the museum's Great Hall — genuinely one of the city's better holiday traditions, not just a seasonal tie-in. Included with regular admission, though the Nov 7 opening day comes with its own tree-lighting and cultural festival if you'd rather catch the full show than wander through later in the run.
Dec1
Sports
Bulls vs. New York Knicks
United Center · Near West Side
Not listed — check United Center/Ticketmaster
The reigning NBA champs' only other trip to the United Center this season, after an Oct. 28 meeting earlier in the year — worth catching live if you'd rather watch the champs' size and depth in person than complain about them from a couch. One of just three Bulls games getting national TV coverage this season, for whatever that's worth.
Nov21
Music & Nightlife
Zac Brown Band: Love & Fear Tour
Allstate Arena · Rosemont
From $87
The stadium-country version of a bar band — a set that swings from radio hits to genuine bluegrass detours over two-plus hours, with Grace Potter opening this time around. Parking alone runs $25, so budget for that before the $87-and-up ticket even enters the math.
Nov8
Sports
Bears vs. Tampa Bay Buccaneers (Sunday Night Football)
Soldier Field · Near South Side
Not listed — check Ticketmaster/StubHub
Prime time makes its only regular-season stop at Soldier Field this year — Baker Mayfield and the Buccaneers on NBC's Sunday Night Football, the kind of national-audience game the Bears don't get handed often. Kickoff's late enough (7:20 PM CT) that this is a night out, not an afternoon one.
Nov7
Family & Free Community
Chicago Toy & Game Fair (ChiTAG)
Donald E. Stephens Convention Center · Rosemont
Not listed — tickets via Eventbrite, price TBA
The country's largest consumer toy and game fair — two days of hands-on demos with next holiday season's toys before they ever hit a shelf. This year's 'Wishlist Weekend' leans into Star Wars' 50th anniversary, and it's moved out to Rosemont rather than downtown, so budget extra drive time if you're coming from the city.
Feb4
Sports
Bulls vs. Oklahoma City Thunder
United Center · Near West Side
From $59
The reigning NBA champs' only trip to the United Center all season — Oklahoma City's been the team everyone else is chasing, and this is the one home date to see that team in person rather than on TV. Tickets start around $59, well below what a Knicks or Lakers visit usually runs.
Feb9
Sports
Bulls vs. Golden State Warriors
United Center · Near West Side
From $154
One of the league's marquee franchises, and tickets are already reflecting it — this is running well above the Bulls' typical weeknight price floor before the season even tips off. A Tuesday-night United Center date worth planning around early.
Dec6
Sports
Blackhawks vs. Edmonton Oilers
United Center · Near West Side
From $52
Connor McDavid — the best hockey player on the planet by pretty much unanimous consent — makes his only regular-season trip through the United Center this year. Bedard should be back from offseason shoulder surgery well before this date, which makes it a real measuring-stick night for Chicago's own franchise center, not just a chance to watch someone else's superstar.
Nov20
Festivals & Street Fairs
Christkindlmarket Aurora
RiverEdge Park · Aurora
Free admission
The suburban sibling to the Daley Plaza market, set along the Fox River instead of downtown concrete — same Bavarian glass mugs and Glühwein, a genuinely different backdrop, and noticeably less of a crowd crush. Friday and Saturday hours run until 9 PM if you want to see it lit up after dark, and Thanksgiving/Christmas Eve get shortened 11-4 hours worth planning around.
Dec6
Food & Drink
Clark Street Cookie Crawl
Clark St. (Fullerton to Diversey) · Lincoln Park
$30 general / $45 boozy
A straightforward premise done well — pay once, walk Clark Street, and collect cookies from whichever participating businesses are handing them out that day, carolers and a Santa photo-op included. The $45 'boozy' tier swaps in spiked hot chocolate stops along the same route, for anyone who wants their cookie crawl to also be a bar crawl.
Sep27
Halloween & Fall Seasonal
Midnight Terror Haunted House (10 Years of Fear)
5520 W 111th St. · Oak Lawn
Not listed — check midnightterrorhauntedhouse.com
Ten years running now, and it's grown into two separate haunted houses under one roof — 60-plus rooms, 100-plus actors, 26,000 square feet, a scale that puts it a level above a neighborhood pop-up haunt. It also runs later into the season than most, straight through the first weekend of November.
⚠ A source listed this as "Friday Sept 27–Saturday Nov 9," but those dates actually fall on a Sunday and a Monday in 2026 — the specific dates are likely correct, the weekday labels aren't; it doesn't run every night, so confirm open nights before going.
Feb3
Festivals & Street Fairs
Chicago Boat, RV & Sail Show
Donald E. Stephens Convention Center · Rosemont
Not listed — tickets online, price TBA
A genuine venue change worth knowing before you drive downtown out of habit — this longtime McCormick Place fixture has moved out to Rosemont for 2027. Five days of actual boats, RVs, and fishing gear you can climb into rather than just look at, which is most of the appeal for anyone who isn't already shopping.
Oct10
Arts & Culture
Don Giovanni (Lyric Opera of Chicago)
Civic Opera House · Loop
From $77
Lyric's 2026/27 season opener, and a genuinely starry one — Mozart's opera directed by Chicago theater legend Robert Falls, conducted by the company's own Maestro Mazzola. Three weeks of performances means real date flexibility, and prices swing more than $25 between showings, so it's worth comparing a few dates before committing.
Dec5
Family & Free Community
Grand Menorah Lighting
Daley Plaza · Loop
Free
A 31-foot menorah lit in the middle of the Loop, with live music and hot holiday snacks, right next to Christkindlmarket's own stalls — genuinely one of downtown's better free winter traditions, not an afterthought tacked onto the Christmas display. The city hasn't confirmed an exact 2026 date yet, but recent years have landed the ceremony on Hanukkah's second night.
⚠ City/organizers haven't formally announced the 2026 date — based on the recent-years pattern of lighting on Hanukkah's 2nd night.
Dec31
Music & Nightlife
Dick Clark's New Year's Rockin' Eve — Live from Chicago
Chicago Riverwalk (Wacker & Franklin) · Loop
Free
For the first time, ABC's national New Year's Eve broadcast leaves its usual Times Square base and sets up a real stage right on the Riverwalk — hometown act Chance the Rapper hosting and performing the countdown, with the Chicago River fireworks timed to go off from the bridges at midnight as the backdrop. Free to attend in person, gates open at 5 PM, hours before the 9 PM performances start.
Dec19
Arts & Culture
Merry, Merry Chicago! (Chicago Symphony Orchestra)
Symphony Center · Loop
From $55
Orchestra Hall dressed for the holidays — carols and seasonal standards with a guest vocalist (Broadway's Mandy Gonzalez this year) instead of a solo classical program, the CSO's own answer to 'The Nutcracker' for people who'd rather hear voices than watch dancing. Five performances over five days means real scheduling flexibility compared to most of the season's other marquee runs.
Family & Free Community
Ice Skating at Millennium Park
McCormick Tribune Ice Rink · Loop
Free (reservation required)
Free ice skating in the shadow of the Bean, reservations required but never a ticket price — one of downtown's most reliable free-winter anchors, running for two decades now. The exact 2026-27 opening date isn't announced yet, but recent seasons have started in late November and run into February.
⚠ City hasn't announced exact 2026-27 season dates yet — based on the recent-years opening pattern (mid-to-late November).
Family & Free Community
CTA Holiday Train
Rotates across all 8 CTA rail lines · Citywide
Regular CTA fare (kids under 7 free)
Six decorated railcars and an open flatcar carrying Santa's sleigh, running a different line's schedule most nights of the season — no special ticket, just regular CTA fare (kids under 7 ride free). Selected Saturday stops add photos with Santa. 2026-27 dates aren't posted yet, but last season ran Nov 28-Dec 22 and this is now a 35-year Chicago tradition.
⚠ CTA hasn't announced the exact 2026 schedule yet — based on 2025's Nov 28–Dec 22 run, check transitchicago.com/holidayfleet closer to the date for the real day-by-line schedule.
Oct31
Family & Free Community
Upside Down Halloween Parade
Washington Park (Russell Dr.) · Washington Park
Free
The Chicago Park District flips the format — instead of watching a parade, kids and families become it, marching costumed down Russell Drive past dance teams, acrobats, and sports mascots doing the entertaining for once. No costume on hand isn't a dealbreaker: 2,000 get given away at the gates.
Sep21
Halloween & Fall Seasonal
Goebbert's Fall Festival & Pumpkin Patch
Goebbert's Farm & Garden Center · South Barrington
$12 weekdays / $15 weekends
A fall festival that's outgrown the word 'pumpkin patch' — a corn maze, a genuine zoo with camel rides, a haunted house, and a jumping pillow all sharing one property. Weekend admission runs $15, weekdays drop to $12, and everyone three and up needs a ticket now, so budget for the whole family rather than assuming little ones ride free.
Feb14
Festivals & Street Fairs
Chicago Chinatown Lunar New Year Parade
Wentworth Ave. (24th St. to Cermak) · Chinatown
Free
Chinatown's biggest day of the year — lion dancers, dragon dancers, marching bands, and firecrackers moving up Wentworth Avenue, the neighborhood's own answer to St. Patrick's Day for scale and turnout. Free to watch, but arrive early: sidewalks along the parade route fill in fast.
Festivals & Street Fairs
Argyle Lunar New Year Celebration
Argyle St. & Sheridan Rd. · Uptown
Free
Uptown's own Lunar New Year tradition, running 40+ years and distinct from Chinatown's Wentworth Avenue parade — a smaller, neighborhood-scale celebration built around Argyle's Vietnamese and Southeast Asian business corridor, with a parade, an art walk, and restaurant specials up and down the strip.
⚠ 2027 date not yet announced — based on 2026's Feb 21 celebration.
Jan16
Sports
Blackhawks vs. Detroit Red Wings
United Center · Near West Side
From $75
One of the NHL's oldest rivalries, dating back to the league's Original Six era — no marketing gimmick needed, just two teams that have been playing each other since before either current arena existed. A January Saturday-night slot, right in the thick of the Hawks' heaviest month of the season.
Jan24
Sports
Blackhawks vs. Vegas Golden Knights
United Center · Near West Side
From $52
Vegas has been one of the NHL's most consistent contenders since entering the league in 2017 — this is their only trip to the United Center all season, landing on a Sunday evening deep in the Hawks' packed January home stand.
Jun27
Festivals & Street Fairs
Chicago Pride Parade
Broadway & Halsted (Lakeview/Boystown route) · Lakeview
Free
Chicago's largest single-day event, period — over a million people lining a route through Lakeview and Boystown, floats and contingents from businesses, politicians, and community groups stretching for hours. Free to watch, and the surrounding neighborhood turns into one giant street party regardless of whether you actually catch a float going by.
May29
Festivals & Street Fairs
Sueños Music Festival
Grant Park · Loop
From $279 (2-day GA)
Chicago's own major Latino music festival, now a real fixture on the summer calendar — two days of reggaeton, Latin trap, and cross-genre headliners in the same park that hosts Lollapalooza. First-round tickets already sold out; a waitlist is the only way in until the next release.
Music & Nightlife
North Coast Music Festival
SeatGeek Stadium · Bridgeview
Not yet listed
Chicago's own Labor Day Weekend electronic-music tradition, heading into its 17th year — 75+ artists across six stages over three days. Not downtown: this one's out in Bridgeview, with the suburban stadium's parking lot as an actual advantage over fighting for a spot near Grant Park.
⚠ 2027 dates not yet formally confirmed — based on the Labor Day weekend pattern (2026 ran Sept 4-6).
Festivals & Street Fairs
Chicago Blues Festival
Millennium Park · Loop
Free
The world's largest free blues festival — a full weekend of national headliners and Chicago's own blues legends filling Pritzker Pavilion, genuinely free admission for a lineup that would cost real money almost anywhere else. 2027 dates haven't been formally confirmed yet, but June has been the reliable home for decades.
⚠ 2027 dates not yet formally confirmed — based on the festival's long-running early-June pattern at Millennium Park.
Mar7
Festivals & Street Fairs
Chicago Flower & Garden Show
Navy Pier (Festival Hall) · Streeterville
$20 adult / $5 child (ages 5–12)
Navy Pier's Festival Hall turned into an indoor spring garden for over a week — full landscaped displays, a vendor marketplace, and cooking demos, useful for anyone tired of Chicago still being gray in early March. It's back at Navy Pier after a two-year stint out in Rosemont, so old habits about where to park may be outdated.
⚠ Sources disagreed on exact dates (March 7-15 vs. March 18-22) — confirm before planning.
Jun12
Festivals & Street Fairs
Wells Street Art Festival
Wells St. (North Ave. to Division St.) · Old Town
Free (gate donations suggested)
Old Town's own art fair, Wells Street closed to traffic for two days of 125+ juried artists and a real live-music lineup across two stages — genuinely free to get in, though the gate donation bins aren't subtle about wanting your five bucks. 2027 dates aren't locked yet, but it's landed on the second weekend of June for years running.
⚠ 2027 dates not yet formally confirmed — based on the festival's second-weekend-of-June pattern (2026 ran June 13-14).
Jun5
Festivals & Street Fairs
57th Street Art Fair
57th St. (Kimbark to Kenwood Ave.) · Hyde Park
Free
Chicago's oldest juried art fair, running since 1948 and still free to walk through — genuinely different from a lot of the city's newer, more commercial street fests, closer to a real juried gallery show that happens to be outdoors in Hyde Park. First weekend of June, like clockwork, for most of its 75-plus-year history.
⚠ 2027 dates not yet formally confirmed — based on the fair's first-weekend-of-June pattern.
May29
Festivals & Street Fairs
Do Division Street Fest
Division St. (Ashland to Leavitt) · West Town
Free (suggested $10 donation)
West Town's Memorial Day weekend fixture — Division Street closed for local and touring bands, food vendors, and beer tents, a genuinely more neighborhood-scale alternative to Wicker Park Fest a few blocks over. The suggested $10 gate donation benefits local nonprofits (Esperanza, Nourishing Hope, Erie House) rather than a for-profit promoter.
⚠ 2027 dates not yet formally confirmed — estimate based on the fest's Memorial Day weekend pattern.
Food & Drink
Taste of Randolph
Randolph St. (near 900 W.) · West Loop
Free
The West Loop's own three-day street fest, built around the neighborhood's actual restaurant scene rather than food-truck fare — genuinely free to get in as of the most recent years, after organizers got called out for charging an online-only cover that flouted the city's free-street-fest rules. Live music runs all three days alongside the food.
⚠ 2027 dates not yet formally confirmed — based on the fest's mid-to-late-June pattern.
May22
Arts & Culture
Pokémon Fossil Museum (Field Museum)
Field Museum · Near South Side
$18/$13 weekdays, $20/$14 weekends (adult/child)
Pokémon and paleontology in the same building, on purpose — real fossil specimens paired with the franchise's own fossil-Pokémon designs, aimed at both actual dinosaur kids and the generation that grew up catching them on a Game Boy. Demand's been high since it opened, so advance booking is worth doing rather than assuming walk-up availability.
Arts & Culture
Anne Frank The Exhibition
Griffin Museum of Science and Industry · Hyde Park
$19 adult/$15 child, plus museum admission ($10 Flex Pass option; free entry ended Sept 2026)
A life-size, fully furnished reconstruction of the Secret Annex where Anne Frank's family and four others hid for two years — walk-through, not behind glass, with an audio guide in English and Spanish. A genuinely different register than the rest of MSI's hands-on science floor.
Nov11
Music & Nightlife
Yo-Yo Ma & the CSO
Symphony Center · Loop
From $155
One of classical music's biggest names returning to play the Shostakovich Cello Concerto No. 1, one of the first concertos he ever recorded, decades into a career built partly on this exact piece. Subscriber priority access has already sold out, and resale is running well above face value — a genuine hot ticket, not just a name-recognition draw.
Feb28
Music & Nightlife
Kodo: One Earth Tour 2027 — Luminance
Symphony Center · Loop
From $45
A world-renowned Japanese taiko drumming ensemble whose shows are as much physical theater as concert — pinpoint-precise choreography built around massive drums, no amplification needed. This edition pays tribute to composer Maki Ishii's Monochrome while premiering new work inspired by the group's recent world travels.
Apr4
Music & Nightlife
Lila Downs
Symphony Center · Loop
From $47
One of Mexico's most acclaimed vocalists, blending indigenous Oaxacan traditions with jazz, cumbia, and boleros into something that doesn't sound quite like anyone else working today. A genuinely global-caliber booking for Symphony Center's non-classical side.
Sep19
Halloween & Fall Seasonal
Fright Fest (Six Flags Great America)
Six Flags Great America · Gurnee
From $45 (park admission); Haunted Attractions Pass priced separately
Six Flags' biggest seasonal transformation of the year — coasters running after dark alongside a rotating slate of haunted mazes, with a new 'Blair Witch: No Signal' maze debuting for the park's 50th anniversary. Park admission (from $45 online) and the separate Haunted Attractions Pass for the mazes are two different costs, so budget for both if the scares matter as much as the rides.
Dec23
Music & Nightlife
Trans-Siberian Orchestra: The Ghosts of Christmas Eve
Allstate Arena · Rosemont
Not listed — check tsochicago.com
A 30th-anniversary staging of 'The Ghosts of Christmas Eve,' with a second set following each night's storyline show — two performances the same day, 2:45 and 8 PM, so a matinee option exists if a late-December school night isn't in the cards. The band's own music director has said ticket prices for this anniversary run were kept lower on purpose, not the usual arena-tour markup.
Nov18
Music & Nightlife
The Neighbourhood
United Center · Near West Side
Varies widely by platform — check before buying
The alt-rock band behind 'Sweater Weather' still packing arenas a decade-plus later — a real United Center headline slot, not a support-act stop. Resale prices swing wildly depending on which platform you check, so it's worth comparing a couple before assuming the first number you see is the going rate.
Dec12
Festivals & Street Fairs
Randolph Street Market: Holiday Market
1341 W. Randolph St. (Plumbers Union Hall) · West Loop
$14 online/$15 door (kids 12 & under free)
The same vintage/antique market moved indoors to the historic Plumbers Union Hall for the holidays — 125+ vendors instead of the summer edition's 300+, but with a real beer/wine/spirits bar and standalone restaurants replacing the food trucks. Same $14 online/$15-door pricing as the outdoor market, and kids 12 and under still get in free.
Dec18
Festivals & Street Fairs
Renegade Craft Fair: Chicago Holiday Market
Bridgeport Art Center · Bridgeport
Free
A different indie-craft brand than Randolph Street Market's antique-focused holiday edition — Renegade skews toward makers: illustrators, ceramicists, small-batch goods, 170+ curated vendors under one roof for a weekend. Free to get in, so the only cost is what you end up buying.
Jun11
Festivals & Street Fairs
Andersonville Midsommarfest
Clark St. (Andersonville) · Andersonville
Free ($10 suggested donation)
Andersonville's own Midsommarfest, a Swedish-heritage neighborhood street fest now in its seventh decade — beer tents, live music across multiple stages, and a genuine Scandinavian throughline in a neighborhood that still has real Swedish bakeries to back it up. The $10 suggested donation goes straight to the Andersonville Chamber of Commerce, same nonprofit model as Do Division.
⚠ 2027 dates not yet formally confirmed — based on the fest's second-weekend-of-June pattern (2026 ran June 12-14).
Jul29
Music & Nightlife
Lollapalooza
Grant Park · Loop
4-day GA historically $365–400+; 2027 pricing not yet announced
Chicago's biggest annual music festival by a wide margin, four days across Grant Park with a lineup that won't be announced for months yet — but the dates are locked in enough to plan a summer around. Four-day GA passes have historically sold out fast and run $365–400+, so this isn't really a decide-in-July kind of ticket.
⚠ Sources disagreed on the exact closing date (Aug 1 vs. Aug 3) — confirm before planning.
Mar14
Festivals & Street Fairs
South Side Irish Parade
Western Ave. (103rd to 111th St.) · Beverly
Free
The South Side's own St. Patrick's tradition, distinct from the downtown Loop parade and river dyeing — Western Avenue closed for a genuinely neighborhood-scale, community-run parade in Beverly, 100+ groups typically marching. It steps off the Sunday before March 17 every year, a pattern that's held for nearly five decades now.
⚠ 2027 date not yet formally confirmed — based on the parade's decades-long Sunday-before-March-17 pattern.
Jun12
Festivals & Street Fairs
Puerto Rican People's Day Parade & Festival
Division St. & Campbell Ave. (Paseo Boricua) · Humboldt Park
Free
Chicago's Puerto Rican community's biggest weekend of the year, now in its fifth decade — floats and musicians down Division Street into a full two-day festival on Paseo Boricua, anchored by the neighborhood's own giant Puerto Rican flag gateways. 2027 dates aren't locked yet, but it's landed on the second Saturday of June for years running.
⚠ 2027 dates not yet formally confirmed — based on the parade's second-Saturday-of-June pattern (2026 ran June 13).
May1
Festivals & Street Fairs
Polish Constitution Day Parade
Columbus Dr. · Grant Park / Loop
Free
One of the largest Polish celebrations outside Poland itself, marking the 1791 constitution's anniversary — folk costumes, floats, and marching bands down Columbus Drive, a real reflection of Chicago having more Polish residents than any city outside Warsaw. Free to watch, and it's landed on the Saturday closest to May 3rd for well over a century.
⚠ 2027 date not yet formally confirmed — based on the parade's century-plus Saturday-closest-to-May-3 pattern (2026 ran May 2).
Oct2
Sports
Northwestern vs. Penn State (New Ryan Field Opener)
Ryan Field · Evanston
Check Ticketmaster/SeatGeek — single-game tickets on sale
The very first football game ever played at the new Ryan Field — a rebuilt, 35,000-seat stadium in Evanston — and Northwestern picked a real Big Ten opponent to break it in with, not a scheduling-filler cupcake. Friday night under the lights on FOX, a road-trip-worthy college football atmosphere about 15 minutes from downtown Chicago.
Dec5
Sports
DePaul vs. SMU (Men's Basketball)
Wintrust Arena · Near South Side
TBD — check DePaulBlueDemons.com
DePaul's own coach called this the toughest non-conference slate the program's put together in his three seasons here, and SMU — a real 2026 NCAA Tournament team — is the headline proof. Wintrust Arena tickets run far cheaper than anything at the United Center, genuinely one of the better deals in Chicago college hoops.
Food & Drink
James Beard Awards Week
Lyric Opera House & venues citywide · Loop
Ceremony sold out to industry; satellite events $175+
The Oscars of the food world, hosted in Chicago every year through at least 2028 — the flagship ceremony at the Lyric Opera sells out to industry insiders (it was gone well before the 2026 date), but the surrounding week is stacked with real public programming: panels, a night market, a 5K, and chef-hosted dinners running $175 and up. Worth building a food-focused week around even without a ceremony ticket.
⚠ Exact 2027 dates not yet announced — based on the ceremony's mid-June pattern.
Apr8
Arts & Culture
EXPO CHICAGO
Navy Pier (Festival Hall) · Streeterville
Not listed — check expochicago.com
Chicago's marquee contemporary and modern art fair — top-tier galleries from around the world setting up at Navy Pier's Festival Hall for four days, the kind of event that spins off a full 'Expo Art Week' of gallery openings and talks well beyond the fair floor itself. A real draw for serious collectors, but browsing carries no obligation to buy.
Jan5
Arts & Culture
Maybe Happy Ending
CIBC Theatre · Loop
From $113 (resale); $49 day-of rush available
Fresh off winning the 2025 Tony for Best Musical, a genuinely odd premise that works — a whirlwind romance between two robots and a houseplant, played for real feeling rather than gimmick. Two weeks only at the CIBC Theatre, and there are $49 day-of rush tickets at the box office for anyone who doesn't want to pay resale prices.
Jan19
Arts & Culture
Oh, Mary!
CIBC Theatre · Loop
Not listed — check Broadway in Chicago
A dark comedy imagining a miserable, suffocated Mary Todd Lincoln in her final weeks before the assassination — genuinely one of the funniest new plays in years per the New York Times, and it won two Tony Awards doing it. It follows Maybe Happy Ending into the same CIBC Theatre slot, making January 2027 an unusually stacked month for that one stage.
Sep29
Arts & Culture
Operation Mincemeat: A New Musical
CIBC Theatre · Loop
From $63
A real WWII deception operation — the Allies planting a corpse with fake invasion plans to fool the Nazis — turned into a genuinely acclaimed musical comedy, extended on Broadway itself through 2027 while this touring production makes its Chicago stop. Real history played for laughs without losing the stakes.
Nov10
Arts & Culture
Jersey Boys
CIBC Theatre · Loop
From $70
Frankie Valli and the Four Seasons' story, still one of the most durable jukebox musicals on tour — 'Sherry,' 'Walk Like a Man,' and 'Big Girls Don't Cry' sung by people who can actually pull off the falsetto. It's the fourth touring show CIBC Theatre hosts this same season, following Operation Mincemeat and preceding Maybe Happy Ending — that one stage is doing a lot of work this year.
Feb4
Arts & Culture
The Comeuppance (Steppenwolf Theatre)
Steppenwolf Theatre (Downstairs Theater) · Lincoln Park
Typically $42–75 (Steppenwolf's usual range)
A Pulitzer and Tony-winning playwright's Chicago premiere — Branden Jacobs-Jenkins' dark comedy, directed by Steppenwolf ensemble member Tina Landau and co-produced with San Francisco's American Conservatory Theater. Steppenwolf tickets typically run $42–75, well under what a comparable Broadway-adjacent run downtown would cost.
Jan23
Arts & Culture
John Proctor is the Villain
Goodman Theatre (Albert Theatre) · Loop
Not listed — check goodmantheatre.org
A Tony-nominated sensation that turns a modern teen-girl lens on 'The Crucible' — genuinely one of the most talked-about new plays of the last few years, now making its Chicago premiere in partnership with Minneapolis's Guthrie Theater. Directed by Marti Lyons at the Goodman's 856-seat Albert Theatre.
Apr17
Arts & Culture
The XIXth (The Nineteenth)
Goodman Theatre · Loop
Not listed — check goodmantheatre.org
A fictional dramatization of the moment Tommie Smith and John Carlos raised their fists on the 1968 Olympic podium — written by Kemp Powers (Pixar's 'Soul,' 'One Night in Miami'), already staged at San Diego's Old Globe before this Chicago premiere. A real historical flashpoint treated as drama, not documentary, by the playwright's own framing.
Feb27
Arts & Culture
FEAST! (Goodman Theatre)
Goodman Theatre · Loop
Not listed — check goodmantheatre.org
A true world premiere from Chicago playwright Calamity West — a satire about power and privilege getting its first-ever staging anywhere, not a touring show passing through. Getting to see a brand-new play before anyone else has is the actual pitch here, not a familiar title.
Arts & Culture
Chicago Theatre Week
Venues citywide · Citywide
$15–$30 per ticket
The city's own restaurant-week equivalent for theater — $15 and $30 tickets to 75+ shows across storefronts, Steppenwolf, Goodman, and everywhere between, run by the League of Chicago Theatres specifically to fill seats during the year's slowest theater month. A genuinely easy way to try three or four shows for what one full-price ticket usually costs.
⚠ 2027 dates not yet announced — based on the 2026 Feb 5-15 window.
Jun3
Arts & Culture
The Lion King
Cadillac Palace Theatre · Loop
From $218 (varies widely by date)
Broadway's biggest visual spectacle, puppetry and masks doing work no movie screen fully captures, running two full months at the Cadillac Palace — a real summer-vacation-worthy anchor for anyone visiting Chicago or just looking for an excuse to dress up. Prices swing wildly by date, with later-June performances noticeably cheaper than the opening weeks.
May4
Arts & Culture
Heartbreakers (Chicago Shakespeare Theater)
Chicago Shakespeare Theater (Upstairs Studio) · Navy Pier / Streeterville
Not listed — check chicagoshakes.com
A world premiere that drops Romeo and Juliet into a sweaty, neon-lit underground, reimagined entirely through Pat Benatar and Neil Giraldo's own catalog — 'Love Is a Battlefield,' 'Heartbreaker,' songs written decades before this mashup existed, now built into a real jukebox-musical retelling. Genuinely new, not a revival of something already staged elsewhere.
Feb9
Arts & Culture
Illinoise
Chicago Shakespeare Theater · Navy Pier / Streeterville
Not listed — check chicagoshakes.com
A genuine hometown-to-Broadway story — this dance musical set entirely to Sufjan Stevens' music had its world premiere right here before a Tony-nominated Broadway run, and now it's back where it started for the theater's 40th anniversary season. Justin Peck's choreography does most of the storytelling; there's barely any dialogue.
Apr22
Arts & Culture
Alvin Ailey American Dance Theater
Auditorium Theatre · South Loop
From $44
The company's annual Chicago stop — new works from contemporary choreographers alongside Ailey's own signature piece, 'Revelations,' which still closes nearly every program decades after its 1960 premiere. A genuine institution, not a touring novelty act, and tickets start well under $60.
Sep26
Family & Free Community
Mid-Autumn Festival Celebration
Set in Stone Gathering Space (Burnham Wildlife Corridor) · Near South Side
Free (RSVP encouraged)
A lakefront moon festival on a stretch of shoreline most Chicagoans have never had a reason to visit — mooncakes, storytelling, a lantern procession, and an actual astronomer running moon-viewing through a telescope, all free. It's a genuine four-way partnership (the Chinese American Museum, the Park District, the Field Museum, and the Nature Conservancy), which is part of why it's landed at a nature corridor instead of Chinatown proper this year.
Sep27
Food & Drink
Andersonville Fall Wine Walk
Clark St., Balmoral & Summerdale (Andersonville) · Andersonville
$40 per ticket
Twenty-plus Andersonville shops and boutiques turned into pop-up tasting stops for one Sunday afternoon, split across two routes so the whole strip doesn't bottleneck at once. Check-in's at the Vintage Market on Catalpa, and it runs rain or shine with no refunds — the neighborhood's spring edition does the same thing every May if this one sells out first.
Apr1
Sports
White Sox Home Opener vs. Milwaukee Brewers
Rate Field · Armour Square / Bridgeport
Not yet announced — check whitesox.com
The Sox open their season on the road in Detroit, but the home opener against the Brewers is a genuine bit of scheduling trivia — the first time Milwaukee's been the home-opener opponent since 1995. First pitch of a new season at 35th and Shields, tickets always cheapest and most available at the gate this early in the year.
Aug6
Sports
White Sox vs. Cubs (Crosstown Classic)
Rate Field · Armour Square / Bridgeport
Not yet announced — check whitesox.com
The Sox and Cubs play both legs of next year's Crosstown Classic inside a single month for once — a three-game set at Wrigley in mid-July, then this return leg at Rate Field three weeks later. City bragging rights only, no playoff stakes, but it's still the rowdiest ticket on the South Side calendar every year it happens.
Jul8
Food & Drink
Windy City Smokeout
United Center (outdoor lots) · Near West Side
Not yet listed — check windycitysmokeout.com
A BBQ-and-country-music mashup that's grown into one of the country's biggest festivals of its kind — national pitmasters smoking in the United Center's own parking lots while a country lineup plays a few steps away. Four days, so a single-day GA ticket is the low-commitment way in if the full pass feels like a lot for a parking-lot festival.
Jul6
Sports
White Sox vs. New York Yankees
Rate Field · Armour Square / Bridgeport
From $116 (resale)
The biggest away draw in baseball makes its only 2027 stop on the South Side, a three-game set right before the All-Star break. The Sox host a real homestand around it (the Diamondbacks follow immediately after), but this is the series that actually moves ticket prices.
May3
Sports
White Sox vs. St. Louis Cardinals
Rate Field · Armour Square / Bridgeport
From $96 (resale)
Not a division rival, but one of baseball's most historic franchises making its only 2027 trip to the South Side — a three-game interleague set in early May, well before the summer crowds show up.
Sep22
Sports
Chicago Sky vs. Toronto Tempo
Wintrust Arena · Near South Side
From $45
The Sky's final home game of the regular season, and a look at the WNBA's newest franchise — Toronto Tempo, one of two expansion teams that just joined the league, making its first-ever visit to Wintrust. Not a playoff berth on the line for Chicago most years, but a cheap, easy way to see a brand-new team before everyone else catches on.
Nov2
Sports
Blackhawks vs. Colorado Avalanche
United Center · Near West Side
From $35
One of the league's most stacked rosters makes its only regular-season Chicago stop early this season, well before the standings sort out who's actually good this year. Historically one of the more reliably competitive tickets on the Blackhawks' home slate regardless of where either team ends up.
Nov13
Sports
Bulls vs. Atlanta Hawks (NBA Cup)
United Center · Near West Side
From $57
Group-play in the Emirates NBA Cup, the league's in-season tournament, which means this one actually counts for something beyond the regular standings — a real shot at a quarterfinal berth and a strange, court-design version of the United Center for the night.
Dec12
Sports
Blackhawks vs. Utah Mammoth
United Center · Near West Side
From $75
Utah's first-ever visit to the United Center under its new name — the former Arizona Coyotes, relocated to Salt Lake City in 2024 and rebranded from the placeholder "Utah Hockey Club" to the Mammoth for this season. A genuinely new team to see, not just a repainted jersey.
Sep24
Halloween & Fall Seasonal
HellsGate Haunted House (with Statesville Prison)
3101 Canal St · Lockport
$40–50 GA; VIP and higher tiers available
The original Statesville Haunted Prison in Lockport closed its own doors years ago, but its cast and characters haven't disappeared — for 2026 they've moved in with HellsGate, merging two of the south suburbs' best-known haunts into one combined attraction on HellsGate's grounds. A genuinely bigger night than either used to offer alone.
Nov14
Family & Free Community
Illumination: Tree Lights at The Morton Arboretum
The Morton Arboretum · Lisle
Tickets typically $21–34; 2026-27 pricing not yet announced
A quieter, more nature-forward alternative to the big downtown light shows — a walking trail through 1,700 wooded acres lit up rather than a fixed display, now in its 14th year with 4 new installations and a new model-train add-on winding through an indoor fantasy woodland.
Nov13
Food & Drink
FOBAB (Festival of Wood & Barrel-Aged Beer)
Credit Union 1 Arena · Near West Side
$85 per session
A nationally recognized beer festival with a genuinely narrow focus — only wood- and barrel-aged beers, the kind breweries save for special releases rather than the taproom lineup. Two separate tasting sessions across the weekend, so a sellout on one night doesn't necessarily close out the whole event.
Oct11
Music & Nightlife
Olivia Rodrigo: The Unraveled Tour
United Center · Near West Side
From $471 (resale)
Two nights, and by a wide margin the priciest resale ticket of the fall on this page — a real measure of how big the Unraveled Tour has gotten. Wolf Alice opens both nights, so the undercard is worth showing up for too, not just filler before the headliner.
Oct14
Music & Nightlife
The Smashing Pumpkins: The Rats In A Cage Tour
United Center · Near West Side
From $92
A hometown arena show for a band that actually formed in Chicago in 1988 — Billy Corgan and company playing the building a few miles from where the whole thing started, not just another stop on the tour map.
Sep19
Halloween & Fall Seasonal
Jack's Pumpkin Pop-Up
Goose Island · Near North Side
$25–35 (weekday/weekend)
A city pumpkin patch that doesn't require the drive to the suburbs — thousands of pumpkins, a corn maze that ends at a hidden bar, carnival games, and axe-throwing, all a short cab ride from downtown. The most convenient real corn maze on this whole page for anyone without a car.
Oct26
Family & Free Community
Trick or Treat on Southport
Southport Ave (Roscoe to Grace) · Lakeview
Free
The Southport Corridor's own business district shuts down to cars for an afternoon of curbside candy, inflatables, and a pumpkin patch — a genuine neighborhood tradition rather than a one-off pop-up, run by the same chamber of commerce that puts on this strip's other street fests.
Oct23
Arts & Culture
Museum After Hours: Secrets and Specimens
Field Museum · Near South Side
Not yet listed — check fieldmuseum.org
A ticketed evening session after the daytime crowds clear out, part of a fall after-hours series the Field Museum runs each September and October — a genuinely different way to see the collections than a normal weekend visit.
Dec5
Festivals & Street Fairs
Logan Square Farmers Market (Winter, Indoor)
Avondale Collective, 2800 N. Milwaukee Ave. · Logan Square
Free
The outdoor market's own cold-weather sibling, running 16 years now — 20-plus vendors move indoors to a converted collective space so the market doesn't just disappear for a third of the year like most others do.
Oct31
Halloween & Fall Seasonal
Wrigleyville Halloween Crawl
Wrigleyville bars · Lakeview
Not yet listed — check Eventbrite
Billed, not falsely, as Chicago's biggest Halloween party — a single ticket covers a run of Wrigleyville's own bars with free dinner buffets and gift cards built in, so it's not just a cover charge stacked on top of whatever each bar already charges. 21+, valid ID required, and the specific bar lineup isn't announced until the night before.
Nov28
Arts & Culture
Vienna Boys Choir: Christmas in Vienna
Symphony Center (Orchestra Hall) · Loop
From $29
A 500-year-old institution's annual holiday stop at Symphony Center — a genuinely different register from the pop-up light shows and Santa photo-ops that dominate this page's December calendar. Afternoon matinee timing, so it's an easy one to build a full day around.
Oct8
Family & Free Community
Bank of America Chicago Marathon Health & Fitness Expo
McCormick Place · Near South Side
Free
Three days of free, open-to-the-public marathon-adjacent programming before race day itself — runners come for bib pickup, but the exhibitor floor of running gear, nutrition brands, and shoe demos is worth a look even for anyone not racing Sunday.
Nov26
Family & Free Community
Life Time Turkey Trot Chicago
Lincoln Park · Lincoln Park
$60 (5K); $65 (8K); $25 (Kids Race)
A 48-year Thanksgiving-morning tradition along the lakefront, with a real kids' race alongside the 5K and 8K, and every entry benefits the Greater Chicago Food Depository — the rare race where the fundraising angle isn't an afterthought bolted onto the bib.
Mar7
Family & Free Community
Polar Plunge Chicago
North Avenue Beach · Lincoln Park
~$100 registration + $200 fundraising minimum (2026 figures; 2027 not yet announced)
Jumping into Lake Michigan in March, on purpose, to raise money for Special Olympics Illinois — the registration fee comes with a fundraising minimum attached, so it's more commitment than a typical charity 5K, but the payoff is one of the more spectacle-driven civic events on the whole calendar.
Nov20
Festivals & Street Fairs
Christkindlmarket Wrigleyville
Gallagher Way (3635 N. Clark St.) · Wrigleyville
Free admission
The Daley Plaza original's own satellite market, now in its eighth season on the plaza next to Wrigley Field — same wooden chalets and mulled wine, but a genuinely different neighborhood feel, and worth pairing with a trip to the ballpark's own gift shop while it's open.
Nov21
Arts & Culture
George Lopez
The Chicago Theatre · Loop
From $48
A stand-up veteran with 30-plus years of specials and sitcom history behind him, at one of Chicago's most ornate downtown theaters rather than a comedy-club stage. A safer bet for a group night out than a club show with an unknown opener lineup.
Oct23
Arts & Culture
The Book of Mormon
Cadillac Palace Theatre · Loop
From $148
The Broadway satire that's been selling out for over a decade, back for another Chicago run at the Palace. Still one of the hardest touring tickets to find cheap, but a nine-performance week means more shot at a decent seat than the usual five-night stand.
Aug14
Festivals & Street Fairs
Bud Billiken Parade & Festival
Dr. Martin Luther King Jr. Drive (35th to 55th St.) · Bronzeville / Washington Park
Free to watch (VIP seating available)
The nation's largest African-American parade, a Chicago institution since 1929, drawing 500,000-plus along a two-mile Bronzeville route before the crowd moves into Washington Park for a free back-to-school festival — school supplies, haircuts, health screenings, a job fair. A genuinely different kind of civic event than anything else on this page.
Aug21
Festivals & Street Fairs
Chicago Air & Water Show
North Avenue Beach / lakefront · Lincoln Park
Free
One of the largest free events of its kind anywhere, running since 1959 — military and civilian aerobatic teams over Lake Michigan, with well over a million people spread along the lakefront to watch. The single biggest addition this page has made to the outer edge of its coverage window, and worth it.
⚠ 2027 dates not yet formally confirmed — based on the show's third-weekend-of-August pattern (2026 ran Aug 15-16).
Aug6
Festivals & Street Fairs
Northalsted Market Days
Halsted St. (Northalsted) · Lakeview / Boystown
Free (suggested $20/day donation)
Chicago's biggest summer street festival by most measures — a half-mile of Halsted shut down for four stages of live music, 250-plus vendors, drag performances, and dance exhibitions across a full weekend. The $20/day suggested donation funds performers and community programs directly, same nonprofit model as the neighborhood's other big street fests.
⚠ 2027 dates not yet formally confirmed — based on the fest's early-August pattern.
Oct25
Halloween & Fall Seasonal
Aville-o-Ween
Andersonville business district (Clark & Farragut) · Andersonville
Free
Andersonville's own neighborhood Halloween — curbside trick-or-treating through the business district plus a dedicated street party at Clark and Farragut with a DJ, games, and a Pooch Costume Contest. Genuinely low-key compared to Southport's or Wrigleyville's versions, aimed squarely at families with young kids.
Oct31
Halloween & Fall Seasonal
Streeterville Doggy (and Kitty) Halloween Party
Museum of Contemporary Art Sculpture Garden · Streeterville
Free (registration required)
39 years running — a costumed pet parade and party in the MCA's own sculpture garden, free, with a pet-toy swap built in. Registration required, but this is a genuinely charming, low-cost morning if the household includes a dog or cat willing to wear a costume.
Apr15
Arts & Culture
Chicago Latino Film Festival
Landmark Century Centre Cinema · Lakeview
$17 general; $12 Mon–Tue; $15 student/senior/member
43 years running and one of the longest-running Latino film festivals in the country — new features, documentaries, and shorts from across Latin America and the U.S. Latino diaspora, at a single accessible venue rather than scattered across the city. Individual screenings, not a single expensive pass, so it's easy to pick just one or two.
Nov3
Food & Drink
Chicago Pizza Summit (10th Anniversary)
Venue TBA · Chicago
Not yet announced
A decade in, this all-you-can-eat pizza tasting event brings together dozens of Chicago pizzerias under one roof for a single night — genuinely one of the only events on this page built entirely around the city's most argued-about food category. Venue and full details for the 10th-anniversary edition weren't announced yet as of this writing.
⚠ Venue and full 2026 details not yet announced — date confirmed, specifics coming soon per organizers.
Nov12
Arts & Culture
Don Pasquale
Lyric Opera House · Loop
From $68
Donizetti's classic comic opera, six performances across two-plus weeks — an easier entry point than the season's heavier dramatic works if opera itself is the unfamiliar part, not the Lyric's building. Baritone Misha Kiria in the title role, soprano Ying Fang as Norina.
Jun4
Arts & Culture
Guys and Dolls
Lyric Opera House · Loop
From $71
The Lyric's summer musical slot returns after a four-season hiatus, and it's not slumming it — opera star Sondra Radvanovsky steps into the classic Damon Runyon musical alongside a full orchestra pit doing the score justice. A rare chance to see a Lyric-scale production of a show most people only know from a school gym stage.
Feb23
Arts & Culture
Hérodiade: An Opera in Concert
Lyric Opera House · Loop
From $114
A rarely heard Massenet grand opera making its long-awaited Lyric debut — presented as a concert rather than a full staging, so the focus is entirely on the voices, led by Clémentine Margaine and Federica Lombardi under conductor Enrique Mazzola. Sung in French with projected titles.
Mar11
Arts & Culture
Ariadne auf Naxos
Lyric Opera House · Loop
From $68
Richard Strauss's opera-within-an-opera, in John Cox's acclaimed production, with tenor Russell Thomas and baritone Zachary Nelson leading a cast built for the score's demanding, high-octane vocal writing. Sung in German with projected titles.
Apr11
Arts & Culture
Susannah
Lyric Opera House · Loop
From $68
Carlisle Floyd's Appalachian fable of innocence and small-town accusation, back at the Lyric for the first time since 2002 — a raw, Broadway-and-folk-inflected American score that plays very differently from the season's European grand operas. Gabriella Reyes stars, with Lyric debuts from Ryan Speedo Green and Matthew Cairns.
Nov20
Family & Free Community
Millennium Park Holiday Market
Millennium Park · Loop
Free
A smaller, artisan-focused counterpart to Daley Plaza's Christkindlmarket a few blocks away — independent Chicago makers selling hand-knit scarves, bath bombs, and other locally made goods under string lights, timed to open the same weekend as the park's own 113th annual tree lighting.
Nov26
Family & Free Community
Naper Lights
Naperville Riverwalk · Naperville
Free
250,000 lights and a growing cast of giant lighted figures — skating polar bears, penguins, carolers — strung along Water Street and the Riverwalk for over a month straight, with free 3D viewing glasses that make certain displays pop. Santa shows up on a rotating schedule of specific nights rather than being there every evening, worth checking before a visit built around meeting him.
Dec4
Festivals & Street Fairs
Geneva Christmas Walk
Geneva Courthouse lawn & downtown · Geneva, IL (western suburb)
Free
A one-night holiday kickoff in one of the western suburbs' most walkable downtowns — Santa Lucia lighting the Great Tree, strolling carolers, roasted chestnuts, and a live nativity on the courthouse lawn, with downtown merchants running their own holiday specials the same evening.
Nov20
Family & Free Community
Chicago Sports Spectacular
Donald E. Stephens Convention Center · Rosemont
Fri $15; Sat/Sun $20/day; kids 10 & under $10
A trading-card and memorabilia show with genuinely broad appeal beyond hardcore collectors — 400-plus exhibitors covering vintage and modern sports cards, Pokémon, and other trading card games, plus 60-plus autograph and photo-op guests from sports and pop culture. A cheap Friday sneak-peek option exists for anyone who just wants to browse before the weekend crowds.
Apr30
Arts & Culture
C2E2 (Chicago Comic & Entertainment Expo)
McCormick Place · Near South Side
Single-day from $50; 3-day from $137
The Midwest's largest pop-culture convention, running since 2010 — three days of comics, cosplay, celebrity panels, and artist alley, all under one roof at McCormick Place. Single-day tickets exist for anyone who just wants one day of it rather than the full weekend commitment.
Apr1
Arts & Culture
Ellen B.
Steppenwolf Theatre (Ensemble Theatre) · Lincoln Park
Not yet listed — check steppenwolf.org
Marius von Mayenburg's psychological thriller gets its English-language premiere here, directed by Whitney White and translated by Daniel Brunet — a genuinely rare first crack at a script most Chicago audiences would otherwise never get to see in English.
May27
Arts & Culture
The Night Fawn
Steppenwolf Theatre (Downstairs Theater) · Lincoln Park
Not yet listed — check steppenwolf.org
A true world premiere by Adam Rapp, directed by ensemble member Terry Kinney and starring ensemble member Cliff Chamberlain — Steppenwolf's season closer, and the kind of new-play risk-taking the company built its reputation on rather than another revival.
Jan3
Sports
Bears vs. Detroit Lions
Soldier Field · Near South Side
Not listed
The final game of the regular season, against a rival Chicago's played nearly as long as it's fielded a team at all — Bears-Lions dates back to the 1930s. Early January at Soldier Field is exactly as cold as that sounds.
Nov7
Food & Drink
Elf'd Up
Stretch Bar & Grill · Wrigleyville
No cover (pay per drink/item)
A Wrigleyville dive goes full Buddy the Elf for the season — candy-cane décor, syrup-forward specialty cocktails, and a holiday menu, no reservation or cover required. First-come, first-served, so weekday afternoons beat a Friday night if you actually want a seat.
⚠ Sources disagree on the exact 2026-27 closing date (one says early January, another mid-January) — confirm on elfdup.com before planning a visit near the end of the run.
Nov5
Music & Nightlife
KATSEYE: The Wildworld Tour
United Center · Near West Side
Not listed
One of pop's fastest-rising acts of the last two years, and the Wildworld Tour is their first swing through arenas rather than theaters — a real measure of how fast the ceiling moved on this six-member, multinational group.
Oct2
Halloween & Fall Seasonal
The Great Highwood Pumpkin Fest
Downtown Highwood · Highwood
Not listed — check celebratehighwood.org
The North Shore's answer to a big-city fall festival — 17 years running, and Highwood's whole small downtown turns into pumpkin-carving walls, carnival rides, and three straight days of live music. A Thursday community prelude gets it started before the main festival even opens.
Nov20
Family & Free Community
Chicago Christmas Tree Lighting Ceremony
Millennium Park · Loop
Free
Not to be confused with the Magnificent Mile Lights Festival the night before — this is the city's own official tree, going up in Millennium Park with a full stage show and a fireworks finale, the same weekend Christkindlmarket opens a few blocks over. Free, and the tree stays lit through Jan 10.
Oct23
Halloween & Fall Seasonal
Zoo Brews: Howls and Growls
Lincoln Park Zoo · Lincoln Park
From $65 (rises to $70 day-of)
The 21-and-up answer to Boo! at the Zoo — trick-or-treat your way between craft beer and cider sample stations set up across the zoo grounds, with roaming entertainers, a costume contest, and a live pumpkin-carving demo. Two nights only, and pricing climbs the closer you wait.
Sep26
Food & Drink
WingOut Chicago
Gallagher Way · Wrigleyville
From $20 GA / $109 VIP
Dozens of Chicago restaurants competing on wings alone — buffalo, wood-smoked, jerk, honey chili, the works — with live soul, R&B, and reggae keeping the Gallagher Way lawn occupied between plates. Book a specific entry session; this isn't a wander-in-whenever event.
Sep27
Family & Free Community
Meet Me on Milwaukee
Milwaukee Ave. (Damen/North to Ashland) · Wicker Park
Free
Milwaukee Avenue goes car-free for the day — the usual traffic swapped for live music, sidewalk sales, outdoor dining tables set up mid-street, and free exercise classes. No registration, no cost, just show up and walk it. Recurs on select Sundays through October.
Dec3
Festivals & Street Fairs
One of a Kind Holiday Show
The Mart (222 Merchandise Mart Plaza, 7th Floor) · River North
$12–$80 depending on day/tier
25th year for what's basically Chicago's biggest holiday craft fair — 600+ independent artists and makers under one roof at The Mart, so it's an actual gift-shopping strategy, not just a browse. Admission scales with the day and ticket tier, so check before you commit to a specific one.
Nov28
Family & Free Community
Winter Flower Show
Garfield Park Conservatory · East Garfield Park
Free (reservation required)
A free, warm, green escape from the coldest stretch of the year — the Conservatory's greenhouses stay in full winter bloom straight through the holidays. Free admission, but they do require a reservation, so this isn't a walk-up.
⚠ 2026-27 dates not yet formally announced by the Conservatory — the range shown is based on last year's schedule; recheck garfieldconservatory.org closer to late November.
Oct31
Halloween & Fall Seasonal
Haunted House Party at Shedd Aquarium
Shedd Aquarium · Near South Side
Not listed — check sheddaquarium.org
House music and Halloween collide after hours, with DJ Gent Hunt and DJ Heather spinning while you have the exhibits mostly to yourselves. 21+, costumes encouraged (full-face masks and prop weapons aren't), and the aquarium's touch experiences stay open the whole night.
Oct31
Sports
Chicago Wolves "Howl-O-Ween Night" vs. Texas Stars
Allstate Arena · Rosemont
Not listed
The family-friendly counter-program to a night full of 21+ parties — trick-or-treating on the concourse, costumes welcome in the stands, and actual AHL hockey (the Wolves are the Vegas Golden Knights' top affiliate) in between candy runs.
Mar13
Sports
Chicago Wolves vs. Toronto Marlies
Allstate Arena · Rosemont
From $23
A real rematch, not just a scheduling coincidence — these two teams met in the 2026 Calder Cup Finals, and the regular season brings them back together for a St. Pat's-weekend doubleheader (jersey auction for autism awareness, bobblehead giveaway Saturday).
Nov7
Sports
Windy City Bulls: 10th Anniversary Celebration
NOW Arena · Hoffman Estates
From $10
The Bulls' G League affiliate marks a full decade with a dedicated anniversary night, one of just six specially-designated home dates on a 24-game schedule. Real NBA-adjacent basketball at a fraction of United Center prices — end-court seats start at $10, and the whole lower bowl tops out well under $50.
Oct23
Arts & Culture
Omar
Lyric Opera House · Loop
Not listed — check lyricopera.org
A Pulitzer Prize winner, co-composed by MacArthur "genius grant" recipient Rhiannon Giddens, telling a true story most opera houses have never touched — the capture, Atlantic crossing, and enslavement of 19th-century Islamic scholar Omar ibn Said, drawn from his own memoir. Three performances only.
Nov28
Arts & Culture
Disney's Encanto in Concert Live to Film
Lyric Opera House · Loop
Not listed — check lyricopera.org
The full film on a big screen with the Lyric Opera Orchestra playing Lin-Manuel Miranda's songs live underneath it — a genuinely different way to experience a movie the under-10 crowd has probably already memorized, and a rare kid-friendly reason to bring them into the Lyric's building at all.
Oct9
Music & Nightlife
MUNA: Gets So Hot Tour
The Salt Shed (Outdoors) · Near North Side
From $128
The synth-pop trio that opened for Chappell Roan and Boygenius bringing their own headlining show home to the Shed's outdoor lot, with Hemlocke Springs opening — a proven, big-room-ready pop act rather than a still-building one.
Oct11
Music & Nightlife
Interpol & DIIV
The Salt Shed (Outdoors) · Near North Side
From $58
Two decades after Turn On the Bright Lights, Interpol still headlines rooms this size — and they're bringing DIIV, one of the more interesting post-punk-revival bands working today, as direct support rather than a warm-up act.
Oct21
Music & Nightlife
The Black Keys: Peaches 'N Kream Tour
The Salt Shed (Indoors) · Near North Side
From $102
A Grammy-winning duo that's still filling rooms this size two decades in, touring behind their upcoming 14th album — the Shed's indoor room is a genuinely good place to hear a guitar-and-drums band without an arena washing it out.
Nov13
Music & Nightlife
Nikki Glaser: The Stunning Tour
The Chicago Theatre · Loop
Not listed
One of the most in-demand stand-ups working right now — post-Golden Globes, post-Tom Brady roast — booked for three straight nights at the Chicago Theatre instead of the usual one-and-done comedy stop. Modern dating and pop culture are the targets; nothing here is safe-for-work.
Mar27
Music & Nightlife
RuPaul's Drag Race: Werq the World Tour
The Chicago Theatre · Loop
Not yet listed
A 10th-anniversary edition of the tour that turned Drag Race stars into a genuine touring act — a news-parody format this year, hosted by Asia O'Hara, with a rotating cast of past-season favorites and surprise guests. Ticket price isn't posted yet, but this is a full arena-style production, not a bar show.
Nov10
Arts & Culture
Dr. Neil deGrasse Tyson: Astronomy Bizarre
Auditorium Theatre · South Loop
From $72
Black holes, dark matter, worm holes, and the simulation-theory question, from the astrophysicist who's spent two decades making that stuff land with a general audience rather than a lecture hall of physics majors. Starts at $72, not the priciest theater booking this fall.
Nov19
Food & Drink
Simply Ina: An Evening with Ina Garten
Auditorium Theatre · South Loop
From $98
The Barefoot Contessa herself, touring behind a new cookbook built around the idea that the best cooking is usually the least complicated. Not a demo or a tasting — this is a stage conversation, so come for the stories and the philosophy more than a live recipe.
Food & Drink
Ribfest Chicago
Lincoln Ave. (Irving Park Rd. to Hutchinson) · Northcenter
$10 suggested donation
Northcenter shuts down a stretch of Lincoln Ave for one of the Midwest's biggest rib cookoffs — 60,000+ people, two stages of live music, and enough grilled pork to fund nearly $400,000 in local community grants over the years off a $10 suggested donation at the gate.
⚠ 2027 dates not yet formally confirmed — based on the first-weekend-of-June pattern (2026 ran June 5-7).
Food & Drink
Chicago Beer Festival
Field Museum · Near South Side
$60 general / $75 early admission
A rare after-hours excuse to wander the Field Museum with a beer in hand — 65+ breweries (3 Floyds, Revolution, Half Acre and beyond) pouring against a backdrop of select open exhibits, 40 tasting vouchers per ticket. Late-February timing means it lands square in the dead of winter, exactly when an indoor festival built around SUE the T. rex sounds appealing.
⚠ 2027 date not yet formally confirmed — based on the late-February pattern (2026 ran Feb 28).
Nov8
Music & Nightlife
Better Than Ezra: Legends of the Fall
House of Blues Chicago · River North
From $80
"Good" and "Desperately Wanting" are still 90s-alt-rock-radio staples, and this tour is exactly the nostalgia stop it sounds like — a full-catalog set for people who had this band on a CD they burned themselves.
Nov19
Music & Nightlife
The Jayhawks
Riviera Theatre · Uptown
From $83
A Minneapolis alt-country band that's been quietly influencing everyone from Wilco to the current Americana revival for three decades, best known outside that circle for "Blue." 18+ show, presented by 93XRT — real local radio credibility, not a syndicated booking.
Nov13
Arts & Culture
Andrew Bird & the CSO
Symphony Center (Orchestra Hall) · Loop
From $109
Bird's first-ever performance with the CSO, and he's using it to play "The Mysterious Production of Eggs" front to back for its 20th anniversary with a full orchestral arrangement — a genuine one-off, not a normal tour stop with strings added. Chicago's own WBEZ and the Sun-Times both ran features on it, not just a ticket-site listing.
Oct9
Music & Nightlife
Shaboozey: Outlaws Never Die Tour
Aragon Ballroom · Uptown
From $81
The biggest crossover country act of the moment, off the back of a song that spent basically all of last year everywhere at once — this is his biggest headline run to date, and the Aragon's ballroom floor is a much rowdier room for it than an amphitheater seat.
Oct2
Music & Nightlife
DJ Shadow: Celebrates 30 Years of Endtroducing
The Vic Theatre · Lakeview
Not listed
"Endtroducing....." is the sample-collage album that made the genre a serious art form and once held the Guinness record for first record made entirely of samples — thirty years on, he's playing it as a full piece, not just dropping the singles into a normal DJ set. 18+.
Nov1
Music & Nightlife
L7: The Last Hurrah Tour
The Vic Theatre · Lakeview
Not listed
The band that famously threw a bloody tampon into a hostile UK festival crowd in 1992 is back, and the tour's own name suggests they mean it as a real goodbye lap, not a normal reunion cash-grab. Riot grrrl-adjacent, still loud, still unbothered.
Nov8
Music & Nightlife
Death From Above 1979: Private Lives Tour
Thalia Hall · Pilsen
From $60
Just a drummer and a bass player making a sound that's somehow louder than most full bands — the Toronto dance-punk duo that's been proving that math for two decades. Wine Lips opens.
Nov23
Music & Nightlife
Kyle Kinane
Thalia Hall · Pilsen
From $84
Deadpan, self-deprecating, and one of the more respected road comics working — the kind of act comedy nerds already know from WTF appearances and Comedy Central specials, booked for two nights instead of the usual one-and-done club set.
Oct17
Music & Nightlife
Rocket From The Crypt: Scream, Frankenstein, Scream! Tour
Metro · Wrigleyville
$36 advance / $41 day-of
San Diego horn-punk lifers touring behind unearthed early tapes from "Scream, Dracula, Scream!" — and The Get Up Kids, genuine emo-scene royalty in their own right, are the opener, not filler. 18+.
Nov14
Music & Nightlife
The Afghan Whigs
Metro · Wrigleyville
$45 advance / $50 day-of
Greg Dulli's band was doing brooding, soul-inflected alt-rock before that was a whole subgenre, and the catalog still holds up. Night Moves opens; there's also a VIP tier with a pre-show Q&A and soundcheck if the standard GA floor isn't enough. 18+.
Oct8
Music & Nightlife
Gorillaz: The Mountain Tour
United Center · Near West Side
From $79
Damon Albarn's cartoon band doesn't tour the U.S. often, so a United Center stop is worth planning around even if you missed the last go-round. Little Simz and Deltron 3030 open, which means the undercard alone would sell tickets on a normal night.
Oct8
Arts & Culture
Chicago Fashion Week
Venues citywide · Citywide
Varies by event — many free or low-cost
Eleven days, and it's deliberately less velvet-rope than the name implies — industry showcases sit on the same calendar as neighborhood-specific programming like the South Side Affair, spotlighting Black women designers and small businesses rather than just the downtown runway crowd. Worth checking the schedule directly since pricing and access vary wildly event to event.
Oct18
Festivals & Street Fairs
Chicago Artisan Market – Fulton Market
Morgan MFG, 401 N. Morgan St. · Fulton Market / West Loop
$8 advance / $10 door
An indoor Sunday market, which matters more than it sounds like in mid-October — no tent, no weather gamble. Food, fashion, home goods, and functional art from independent makers, not the same resale-vintage crowd you'll find at Randolph Street Market a few blocks over.
Oct10
Food & Drink
West Pullman Food Truck Festival
821 W. 115th St. · West Pullman / Far South Side
Not listed
A genuine Far South Side food truck gathering, not a downtown-adjacent one — eight trucks, a live band, and a family fun zone on 115th Street, hosted by the neighborhood's own Far South Community Development Corporation. Real programming for a part of the city that doesn't usually get the festival circuit's attention.
Oct28
Sports
Bulls vs. New York Knicks (First Meeting)
United Center · Near West Side
From $111 (resale)
The first of two meetings with the defending NBA champs this season — the Dec. 1 rematch already has its own listing here, but this is where the season series actually starts. Early litmus test for whether this year's Bulls roster is a real step forward or just a better-looking loss.
Oct30
Halloween & Fall Seasonal
MEMENTO MORI Halloween Gala
International Museum of Surgical Science, 1524 N. Lake Shore Dr. · Gold Coast
Not listed
A Halloween gala held inside an actual museum of surgical history — 19th-century instruments and anatomical art as the backdrop instead of a rented ballroom. Fifth year running, benefits the museum directly, and reads as genuinely different from the standard costume bar crawl.
Oct31
Family & Free Community
Xempasúchil (Día de los Muertos in Little Village)
26th Street commercial corridor · Little Village / South Lawndale
Free
Little Village's own Día de los Muertos weekend — ofrendas built by local businesses along 26th Street, live catrinas working the block, free traditional food and drink handed out storefront to storefront. Feels like a neighborhood remembering out loud, not a museum exhibit about the tradition.
Nov1
Family & Free Community
SKECHERS Hot Chocolate Run Chicago
Grant Park · Loop
5K $39 / 10K $49 / 15K $59
Grant Park on a November morning, thousands of runners chasing a finisher's mug of actual hot chocolate instead of a medal nobody displays. 5K, 10K, and 15K options, plus a 2-mile walk, and the post-race party runs on chocolate fondue rather than bananas and bagels.
Nov1
Sports
Chicago Wolves vs. Grand Rapids Griffins
Allstate Arena · Rosemont
From $20
A Sunday-afternoon AHL game — cheaper and calmer than a Blackhawks night downtown, with the same fast, physical hockey one level down. The Griffins are a longtime divisional rival, so there's an actual stake in it beyond the ticket price.
Nov20
Music & Nightlife
Marc Maron: Yammering into the Void Tour
The Vic Theatre · Lakeview
From $68
The WTF podcast made him one of the format's actual originators, and the new hour leans into the same unfiltered, over-thinking-everything voice that built that show. The Vic's a good room for it — small enough that the crowd work still lands.
Sep8
Arts & Culture
Jekyll & Hyde
Broadway Playhouse at Water Tower Place · Near North Side
Check broadwayinchicago.com for pricing
Kokandy Productions' storefront revival of the Wildhorn/Bricusse musical made the unusual jump from a small nonprofit stage to a full Broadway In Chicago sit-down after selling out and extending — a genuine local-theater-makes-good story, not just another touring import.
Oct13
Arts & Culture
Waitress
James M. Nederlander Theatre · Loop
Check broadwayinchicago.com for pricing
Sara Bareilles' songbook carries this one — 'She Used to Be Mine' still lands as one of the better character-defining ballads in a modern jukebox-adjacent score, even for people who groan at 'movie turned into a musical.'
⚠ A couple of ticket vendors list this run at the Cadillac Palace instead — Broadway In Chicago's own site places it at the Nederlander Theatre; confirm your venue before heading downtown.
Nov24
Arts & Culture
Blue Man Group: A New Holiday Surprise
CIBC Theatre · Loop
$39–$120
Blue Man Group's first-ever holiday show, anywhere — Chicago gets it before any other city does. Same paint-drum-and-toilet-paper physical comedy the franchise built its name on, just pointed at Christmas instead of the usual plotless spectacle.
Nov24
Arts & Culture
The Hip Hop Nutcracker
Cadillac Palace Theatre · Loop
Check broadwayinchicago.com for pricing
Tchaikovsky's score re-scored and danced as hip hop, with a DJ and a violinist on stage alongside the dancers — a genuinely different family-holiday option from the traditional Nutcracker if you've already seen the Joffrey's a few times.
Nov24
Arts & Culture
Mrs. Doubtfire
James M. Nederlander Theatre · Loop
Check broadwayinchicago.com for pricing
The 1993 movie's premise turned into a full musical comedy, directed by four-time Tony winner Jerry Zaks — one week only, and it shares the same November 24 opening weekend as three other Broadway In Chicago shows, an unusually stacked holiday week even for this town.
Sep29
Music & Nightlife
Lambchop (with Daughter of Swords)
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
Kurt Wagner's long-running Nashville outfit slides between deadpan country, jazz chords, and genuinely strange arrangements record to record — the kind of show where the setlist is the real mystery, not just the opener.
Oct4
Music & Nightlife
The Bad Plus — Farewell Tour
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
One of the more inventive piano-trio jazz acts of the last two decades is calling it — genre-agnostic instrumental sets that borrowed as much from indie rock and pop covers as from straight jazz. A real closing chapter, not just another tour stop.
Oct9
Music & Nightlife
Rufus Wainwright — Solo Tour
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
Just voice and piano, no band to hide behind — Wainwright's baroque-pop songwriting actually holds up stripped down this far, which isn't true of every artist who tries a 'solo tour.'
Oct10
Music & Nightlife
John Prine 80th Birthday Celebration
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
A daytime tribute gathering for one of Chicago's own — Prine worked as a mail carrier on the city's North Side before Kris Kristofferson helped launch his career, and Old Town School has stayed one of the real centers of that folk lineage ever since.
Oct23
Music & Nightlife
Judy Collins — Sweet Judy Blue Eyes: Farewell
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
A genuine farewell run, not a marketing label — Collins is in her late 80s and this is billed as her actual final tour. 'Both Sides Now' and 'Send in the Clowns' both still belong to her as much as to whoever wrote them.
Nov7
Music & Nightlife
Lucinda Williams
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
A four-night stand in one room is a rare thing to book this far out — Williams has been touring behind a stroke recovery that reportedly changed her guitar playing, not her voice, and by all accounts the band fills in the difference rather than working around it.
Nov25
Music & Nightlife
Rickie Lee Jones
Old Town School of Folk Music (Maurer Hall) · Lincoln Square
Check oldtownschool.org for pricing
'Chuck E.'s in Love' made her a star in 1979 and she's spent the decades since actively resisting being only that — expect a set that leans on her sprawling catalog rather than a nostalgia victory lap.
Sep25
Family & Free Community
Andersonville Arts Weekend
Clark St. (Andersonville) · Andersonville
Free
Thirty-plus Clark Street shops and restaurants turn into pop-up galleries for a weekend, no ticket booth or wristband required — this is the neighborhood's 22nd year doing it, and locals treat it less like an 'event' than an excuse to actually walk into the businesses they usually just pass. Opening receptions kick off Friday night; free portrait sessions and neighborhood history tours round out the weekend.
Nov7
Music & Nightlife
Orville Peck: Man Turned Mule Tour
The Salt Shed (Indoor) · Goose Island
Not listed
The masked country outlaw brings the Man Turned Mule Tour to the Shed's indoor stage, trading the early rhinestone-fringe theatrics for something more stripped-down and road-worn. A dollar from every ticket goes to The Trevor Project, which tells you plenty about who this show is actually built for.
Nov15
Arts & Culture
Moving Identities: 16 Voices of Belonging
Chicago Cultural Center · The Loop
Free
Sixteen LGBTQI+ artists with Chicago ties get a proper gallery room at the Cultural Center — painting, photography, textile, mixed media, all circling questions of access, autonomy, and care rather than just Pride-month posturing. Free, walk-in, and closes mid-November, so it's not a catch-it-next-time kind of show.
Sep17
Arts & Culture
Reeling: The Chicago LGBTQ+ International Film Festival
Landmark Century Centre Cinema · Lincoln Park
$15 general/$13 members per film; passes from $65
The world's second-oldest LGBTQ+ film festival, now in its 44th year — 36 features and 59 shorts from 22 countries over 11 straight days, not a one-weekend token gesture. Individual tickets and multi-film passes are both on sale, so a late start on planning still leaves real options.
Nov6
Music & Nightlife
Jai Wolf: 10 Year Anniversary Tour
Concord Music Hall · Logan Square
$25 GA
Ten years since the electronic producer broke out behind 'Indian Summer,' and he's marking it with an anniversary tour instead of another single-album victory lap. 18+, and a mid-size room rather than an arena keeps this one feeling like an actual show, not a spectacle.
Jan15
Sports
Chicago Cubs Convention 2027
Sheraton Grand Chicago Riverwalk · Streeterville
Not yet listed (2025 weekend pass was $125)
Three days of panels, autograph lines, and off-season small talk with players and front-office staff — the 28th annual edition of what's really the fanbase's own midwinter holiday more than a trade-show convention. Weekend-pass pricing for 2027 isn't posted yet; 2025's ran $125.
Nov21
Family & Free Community
Holiday Magic at Brookfield Zoo Chicago
Brookfield Zoo Chicago · Brookfield, IL (western suburb)
From $29.95; free for members
3.5 million lights, a light-up maze, and a Holiday Dolphin Show make Brookfield's answer to Lincoln Park's ZooLights a real destination on its own, not just the suburban backup option. A dedicated sensory-friendly night (Wed Dec 3) is a genuinely useful detail most holiday-lights events don't bother offering.
⚠ Located in Brookfield, a western suburb, not the city proper.
Mar16
Sports
Blackhawks vs. San Jose Sharks
United Center · Near West Side
From $45
Macklin Celebrini, the No. 1 pick from 2024 and already an alternate captain at 20, brings the rebuilding Sharks to the United Center for their only Chicago stop of the season — a good one to catch if you want to see the league's next wave of stars before the price of admission catches up.
Oct25
Family & Free Community
Harvest on Harrison
Harrison St. (Oak Park Arts District) · Oak Park, IL (western suburb)
Free
Oak Park's arts district turns Harrison Street into a free afternoon of gallery receptions, a kids' nature-STEM workshop, and live music — small, walkable, and the kind of neighborhood event that never makes the big festival roundups but is genuinely worth the trip west.
⚠ Located in Oak Park, a western suburb, not the city proper.
Nov27
Music & Nightlife
A Drag Queen Christmas
Riviera Theatre · Uptown
From $132
Nina West hosts the self-proclaimed longest-running drag tour in America for its annual Riviera stop — a full holiday production built around RuPaul's Drag Race alums, not just a club night with tinsel taped to the walls. 18+, and a genuinely different Chicago holiday tradition than the tree-lighting circuit.
Dec11
Arts & Culture
Elf in Concert
Symphony Center · Loop
From $79
The 2003 Will Ferrell movie plays in full on the big screen while the Chicago Symphony Orchestra performs the score live underneath it — the same film-with-orchestra format the CSO has run for other family titles, just with more yelling about maple syrup.
Jan26
Arts & Culture
All Things Equal: The Life & Trials of Ruth Bader Ginsburg
Broadway Playhouse at Water Tower Place · Near North Side
Not yet listed
Michelle Azar reprises the role she originated, cramming RBG's landmark cases and unlikely friendships (Scalia included) into 90 focused minutes. It's a short, three-night stand rather than an extended run, so it's genuinely easy to miss if you're not watching for it.
Sep18
Halloween & Fall Seasonal
Kuipers Family Farm Fall Harvest Fest (25th Anniversary)
Kuipers Family Farm · Maple Park, IL (western exurb)
$26.99 weekend admission
Twenty-five years in, this working farm's fall season runs a full six weeks — corn maze, pig races, a duck pond, and a U-pick apple orchard alongside the usual pumpkin patch, more actual farm than seasonal pop-up. A real alternative to Goebbert's and Richardson's, further out past St. Charles.
⚠ Located in Maple Park, a far-western exurb (near St. Charles), not the city proper.
Mar5
Family & Free Community
Monster Jam
Allstate Arena · Rosemont, IL (western suburb)
From $35
Ten-foot-tall trucks doing donuts and backflips for a weekend — pure kid-magnet spectacle that doesn't need a cultural hook to justify the trip. Three days of shows means there's almost always a slot that fits a Saturday-morning family schedule.
⚠ Located in Rosemont, a western suburb, not the city proper.
Nov8
Sports
Bulls vs. Philadelphia 76ers (Nov 8)
United Center · Near West Side
From $152
A weekend home date against Philadelphia 76ers — easier to plan around than most on this schedule.
Nov11
Sports
Bulls vs. San Antonio Spurs
United Center · Near West Side
From $92
A regular weeknight home date against San Antonio Spurs at the United Center.
Nov20
Sports
Bulls vs. Washington Wizards
United Center · Near West Side
From $42
A regular weeknight home date against Washington Wizards at the United Center.
Nov22
Sports
Bulls vs. Denver Nuggets
United Center · Near West Side
From $54
A weekend home date against Denver Nuggets — easier to plan around than most on this schedule.
Nov23
Sports
Bulls vs. Cleveland Cavaliers (Nov 23)
United Center · Near West Side
From $41
A regular weeknight home date against Cleveland Cavaliers at the United Center.
Nov28
Sports
Bulls vs. Indiana Pacers (Nov 28)
United Center · Near West Side
From $79
A weekend home date against Indiana Pacers — easier to plan around than most on this schedule.
Dec3
Sports
Bulls vs. Cleveland Cavaliers (Dec 3)
United Center · Near West Side
From $49
Second of two meetings with Cleveland Cavaliers this season at the United Center.
Dec13
Sports
Bulls vs. Houston Rockets
United Center · Near West Side
From $58
A weekend home date against Houston Rockets — easier to plan around than most on this schedule.
Dec14
Sports
Bulls vs. Miami Heat
United Center · Near West Side
From $59
A regular weeknight home date against Miami Heat at the United Center.
Dec16
Sports
Bulls vs. Utah Jazz
United Center · Near West Side
From $37
A regular weeknight home date against Utah Jazz at the United Center.
Dec26
Sports
Bulls vs. Detroit Pistons (Dec 26)
United Center · Near West Side
From $100
A weekend home date against Detroit Pistons — easier to plan around than most on this schedule.
Dec30
Sports
Bulls vs. Boston Celtics (Dec 30)
United Center · Near West Side
From $91
A regular weeknight home date against Boston Celtics at the United Center.
Jan2
Sports
Bulls vs. Los Angeles Lakers
United Center · Near West Side
From $162
A weekend home date against Los Angeles Lakers — easier to plan around than most on this schedule.
Jan5
Sports
Bulls vs. Milwaukee Bucks (Jan 5)
United Center · Near West Side
From $40
A regular weeknight home date against Milwaukee Bucks at the United Center.
Jan14
Sports
Bulls vs. Minnesota Timberwolves
United Center · Near West Side
From $56
A regular weeknight home date against Minnesota Timberwolves at the United Center.
Jan17
Sports
Bulls vs. Toronto Raptors
United Center · Near West Side
From $47
A weekend home date against Toronto Raptors — easier to plan around than most on this schedule.
Jan23
Sports
Bulls vs. Philadelphia 76ers (Jan 23)
United Center · Near West Side
From $158
Second of two meetings with Philadelphia 76ers this season at the United Center.
Jan25
Sports
Bulls vs. Dallas Mavericks
United Center · Near West Side
From $48
A regular weeknight home date against Dallas Mavericks at the United Center.
Feb6
Sports
Bulls vs. New Orleans Pelicans
United Center · Near West Side
From $54
A weekend home date against New Orleans Pelicans — easier to plan around than most on this schedule.
Feb25
Sports
Bulls vs. Atlanta Hawks
United Center · Near West Side
From $44
A regular weeknight home date against Atlanta Hawks at the United Center.
Feb27
Sports
Bulls vs. Brooklyn Nets
United Center · Near West Side
From $58
A weekend home date against Brooklyn Nets — easier to plan around than most on this schedule.
Mar6
Sports
Bulls vs. Charlotte Hornets (Mar 6)
United Center · Near West Side
From $54
A weekend home date against Charlotte Hornets — easier to plan around than most on this schedule.
Mar7
Sports
Bulls vs. Portland Trail Blazers
United Center · Near West Side
From $58
A weekend home date against Portland Trail Blazers — easier to plan around than most on this schedule.
Mar9
Sports
Bulls vs. Boston Celtics (Mar 9)
United Center · Near West Side
From $67
Second of two meetings with Boston Celtics this season at the United Center.
Mar11
Sports
Bulls vs. Phoenix Suns
United Center · Near West Side
From $44
A regular weeknight home date against Phoenix Suns at the United Center.
Mar13
Sports
Bulls vs. Memphis Grizzlies
United Center · Near West Side
From $64
A weekend home date against Memphis Grizzlies — easier to plan around than most on this schedule.
Mar15
Sports
Bulls vs. Orlando Magic (Mar 15)
United Center · Near West Side
From $44
A regular weeknight home date against Orlando Magic at the United Center.
Mar22
Sports
Bulls vs. Sacramento Kings
United Center · Near West Side
From $39
A regular weeknight home date against Sacramento Kings at the United Center.
Mar24
Sports
Bulls vs. Orlando Magic (Mar 24)
United Center · Near West Side
From $44
Second of two meetings with Orlando Magic this season at the United Center.
Mar27
Sports
Bulls vs. LA Clippers
United Center · Near West Side
From $58
A weekend home date against LA Clippers — easier to plan around than most on this schedule.
Mar29
Sports
Bulls vs. Indiana Pacers (Mar 29)
United Center · Near West Side
From $46
Second of two meetings with Indiana Pacers this season at the United Center.
Apr2
Sports
Bulls vs. Detroit Pistons (Apr 2)
United Center · Near West Side
From $63
Second of two meetings with Detroit Pistons this season at the United Center.
Apr7
Sports
Bulls vs. Charlotte Hornets (Apr 7)
United Center · Near West Side
From $38
Second of two meetings with Charlotte Hornets this season at the United Center.
Apr9
Sports
Bulls vs. Milwaukee Bucks (Apr 9)
United Center · Near West Side
From $54
Second of two meetings with Milwaukee Bucks this season at the United Center.
Mar27
Sports
Cubs vs. Cleveland Guardians (Mar 27)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cleveland Guardians at Wrigley Field.
Mar28
Sports
Cubs vs. Cleveland Guardians (Mar 28)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cleveland Guardians at Wrigley Field.
Mar29
Sports
Cubs vs. St. Louis Cardinals (Mar 29)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Mar30
Sports
Cubs vs. St. Louis Cardinals (Mar 30)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Mar31
Sports
Cubs vs. St. Louis Cardinals (Mar 31)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Apr9
Sports
Cubs vs. Texas Rangers (Apr 9)
Wrigley Field · Lakeview
From $22
Regular-season home game against Texas Rangers at Wrigley Field.
Apr10
Sports
Cubs vs. Texas Rangers (Apr 10)
Wrigley Field · Lakeview
From $22
Regular-season home game against Texas Rangers at Wrigley Field.
Apr11
Sports
Cubs vs. Texas Rangers (Apr 11)
Wrigley Field · Lakeview
From $22
Regular-season home game against Texas Rangers at Wrigley Field.
Apr13
Sports
Cubs vs. Philadelphia Phillies (Apr 13)
Wrigley Field · Lakeview
From $22
Regular-season home game against Philadelphia Phillies at Wrigley Field.
Apr14
Sports
Cubs vs. Philadelphia Phillies (Apr 14)
Wrigley Field · Lakeview
From $22
Regular-season home game against Philadelphia Phillies at Wrigley Field.
Apr15
Sports
Cubs vs. Philadelphia Phillies (Apr 15)
Wrigley Field · Lakeview
From $22
Regular-season home game against Philadelphia Phillies at Wrigley Field.
Apr23
Sports
Cubs vs. Pittsburgh Pirates (Apr 23)
Wrigley Field · Lakeview
From $22
Regular-season home game against Pittsburgh Pirates at Wrigley Field.
Apr24
Sports
Cubs vs. Pittsburgh Pirates (Apr 24)
Wrigley Field · Lakeview
From $22
Regular-season home game against Pittsburgh Pirates at Wrigley Field.
Apr25
Sports
Cubs vs. Pittsburgh Pirates (Apr 25)
Wrigley Field · Lakeview
From $22
Regular-season home game against Pittsburgh Pirates at Wrigley Field.
Apr26
Sports
Cubs vs. Milwaukee Brewers (Apr 26)
Wrigley Field · Lakeview
From $22
Regular-season home game against Milwaukee Brewers at Wrigley Field.
Apr27
Sports
Cubs vs. Milwaukee Brewers (Apr 27)
Wrigley Field · Lakeview
From $22
Regular-season home game against Milwaukee Brewers at Wrigley Field.
Apr28
Sports
Cubs vs. Milwaukee Brewers (Apr 28)
Wrigley Field · Lakeview
From $22
Regular-season home game against Milwaukee Brewers at Wrigley Field.
May7
Sports
Cubs vs. Seattle Mariners (May 7)
Wrigley Field · Lakeview
From $22
Regular-season home game against Seattle Mariners at Wrigley Field.
May8
Sports
Cubs vs. Seattle Mariners (May 8)
Wrigley Field · Lakeview
From $22
Regular-season home game against Seattle Mariners at Wrigley Field.
May9
Sports
Cubs vs. Seattle Mariners (May 9)
Wrigley Field · Lakeview
From $22
Regular-season home game against Seattle Mariners at Wrigley Field.
May11
Sports
Cubs vs. Miami Marlins (May 11)
Wrigley Field · Lakeview
From $22
Regular-season home game against Miami Marlins at Wrigley Field.
May12
Sports
Cubs vs. Miami Marlins (May 12)
Wrigley Field · Lakeview
From $22
Regular-season home game against Miami Marlins at Wrigley Field.
May13
Sports
Cubs vs. Miami Marlins (May 13)
Wrigley Field · Lakeview
From $22
Regular-season home game against Miami Marlins at Wrigley Field.
May21
Sports
Cubs vs. Washington Nationals (May 21)
Wrigley Field · Lakeview
From $22
Regular-season home game against Washington Nationals at Wrigley Field.
May22
Sports
Cubs vs. Washington Nationals (May 22)
Wrigley Field · Lakeview
From $22
Regular-season home game against Washington Nationals at Wrigley Field.
May23
Sports
Cubs vs. Washington Nationals (May 23)
Wrigley Field · Lakeview
From $22
Regular-season home game against Washington Nationals at Wrigley Field.
May25
Sports
Cubs vs. Kansas City Royals (May 25)
Wrigley Field · Lakeview
From $22
Regular-season home game against Kansas City Royals at Wrigley Field.
May26
Sports
Cubs vs. Kansas City Royals (May 26)
Wrigley Field · Lakeview
From $22
Regular-season home game against Kansas City Royals at Wrigley Field.
May27
Sports
Cubs vs. Kansas City Royals (May 27)
Wrigley Field · Lakeview
From $22
Regular-season home game against Kansas City Royals at Wrigley Field.
Jun3
Sports
Cubs vs. Los Angeles Dodgers (Jun 3)
Wrigley Field · Lakeview
From $22
Regular-season home game against Los Angeles Dodgers at Wrigley Field.
Jun4
Sports
Cubs vs. Los Angeles Dodgers (Jun 4)
Wrigley Field · Lakeview
From $22
Regular-season home game against Los Angeles Dodgers at Wrigley Field.
Jun5
Sports
Cubs vs. Los Angeles Dodgers (Jun 5)
Wrigley Field · Lakeview
From $22
Regular-season home game against Los Angeles Dodgers at Wrigley Field.
Jun6
Sports
Cubs vs. Los Angeles Dodgers (Jun 6)
Wrigley Field · Lakeview
From $22
Regular-season home game against Los Angeles Dodgers at Wrigley Field.
Jun11
Sports
Cubs vs. Colorado Rockies (Jun 11)
Wrigley Field · Lakeview
From $22
Regular-season home game against Colorado Rockies at Wrigley Field.
Jun12
Sports
Cubs vs. Colorado Rockies (Jun 12)
Wrigley Field · Lakeview
From $22
Regular-season home game against Colorado Rockies at Wrigley Field.
Jun13
Sports
Cubs vs. Colorado Rockies (Jun 13)
Wrigley Field · Lakeview
From $22
Regular-season home game against Colorado Rockies at Wrigley Field.
Jun14
Sports
Cubs vs. Cincinnati Reds (Jun 14)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Jun15
Sports
Cubs vs. Cincinnati Reds (Jun 15)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Jun16
Sports
Cubs vs. Cincinnati Reds (Jun 16)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Jul1
Sports
Cubs vs. St. Louis Cardinals (Jul 1)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Jul2
Sports
Cubs vs. St. Louis Cardinals (Jul 2)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Jul3
Sports
Cubs vs. St. Louis Cardinals (Jul 3)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Jul16
Sports
Cubs vs. Chicago White Sox (Jul 16)
Wrigley Field · Lakeview
From $22
Regular-season home game against Chicago White Sox at Wrigley Field.
Jul17
Sports
Cubs vs. Chicago White Sox (Jul 17)
Wrigley Field · Lakeview
From $22
Regular-season home game against Chicago White Sox at Wrigley Field.
Jul18
Sports
Cubs vs. Chicago White Sox (Jul 18)
Wrigley Field · Lakeview
From $22
Regular-season home game against Chicago White Sox at Wrigley Field.
Jul19
Sports
Cubs vs. Pittsburgh Pirates (Jul 19)
Wrigley Field · Lakeview
From $22
Regular-season home game against Pittsburgh Pirates at Wrigley Field.
Jul20
Sports
Cubs vs. Pittsburgh Pirates (Jul 20)
Wrigley Field · Lakeview
From $22
Regular-season home game against Pittsburgh Pirates at Wrigley Field.
Jul21
Sports
Cubs vs. Pittsburgh Pirates (Jul 21)
Wrigley Field · Lakeview
From $22
Regular-season home game against Pittsburgh Pirates at Wrigley Field.
Jul30
Sports
Cubs vs. Boston Red Sox (Jul 30)
Wrigley Field · Lakeview
From $22
Regular-season home game against Boston Red Sox at Wrigley Field.
Jul31
Sports
Cubs vs. Boston Red Sox (Jul 31)
Wrigley Field · Lakeview
From $22
Regular-season home game against Boston Red Sox at Wrigley Field.
Aug1
Sports
Cubs vs. Boston Red Sox (Aug 1)
Wrigley Field · Lakeview
From $22
Regular-season home game against Boston Red Sox at Wrigley Field.
Aug2
Sports
Cubs vs. San Francisco Giants (Aug 2)
Wrigley Field · Lakeview
From $22
Regular-season home game against San Francisco Giants at Wrigley Field.
Aug3
Sports
Cubs vs. San Francisco Giants (Aug 3)
Wrigley Field · Lakeview
From $22
Regular-season home game against San Francisco Giants at Wrigley Field.
Aug4
Sports
Cubs vs. San Francisco Giants (Aug 4)
Wrigley Field · Lakeview
From $22
Regular-season home game against San Francisco Giants at Wrigley Field.
Aug9
Sports
Cubs vs. St. Louis Cardinals (Aug 9)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Aug10
Sports
Cubs vs. St. Louis Cardinals (Aug 10)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Aug11
Sports
Cubs vs. St. Louis Cardinals (Aug 11)
Wrigley Field · Lakeview
From $22
Regular-season home game against St. Louis Cardinals at Wrigley Field.
Aug13
Sports
Cubs vs. Tampa Bay Rays (Aug 13)
Wrigley Field · Lakeview
From $22
Regular-season home game against Tampa Bay Rays at Wrigley Field.
Aug14
Sports
Cubs vs. Tampa Bay Rays (Aug 14)
Wrigley Field · Lakeview
From $22
Regular-season home game against Tampa Bay Rays at Wrigley Field.
Aug15
Sports
Cubs vs. Tampa Bay Rays (Aug 15)
Wrigley Field · Lakeview
From $22
Regular-season home game against Tampa Bay Rays at Wrigley Field.
Aug16
Sports
Cubs vs. Arizona Diamondbacks (Aug 16)
Wrigley Field · Lakeview
From $22
Regular-season home game against Arizona Diamondbacks at Wrigley Field.
Aug17
Sports
Cubs vs. Arizona Diamondbacks (Aug 17)
Wrigley Field · Lakeview
From $22
Regular-season home game against Arizona Diamondbacks at Wrigley Field.
Aug18
Sports
Cubs vs. Arizona Diamondbacks (Aug 18)
Wrigley Field · Lakeview
From $22
Regular-season home game against Arizona Diamondbacks at Wrigley Field.
Aug27
Sports
Cubs vs. Atlanta Braves (Aug 27)
Wrigley Field · Lakeview
From $22
Regular-season home game against Atlanta Braves at Wrigley Field.
Aug28
Sports
Cubs vs. Atlanta Braves (Aug 28)
Wrigley Field · Lakeview
From $22
Regular-season home game against Atlanta Braves at Wrigley Field.
Aug29
Sports
Cubs vs. Atlanta Braves (Aug 29)
Wrigley Field · Lakeview
From $22
Regular-season home game against Atlanta Braves at Wrigley Field.
Aug30
Sports
Cubs vs. Milwaukee Brewers (Aug 30)
Wrigley Field · Lakeview
From $22
Regular-season home game against Milwaukee Brewers at Wrigley Field.
Aug31
Sports
Cubs vs. Milwaukee Brewers (Aug 31)
Wrigley Field · Lakeview
From $22
Regular-season home game against Milwaukee Brewers at Wrigley Field.
Sep1
Sports
Cubs vs. Milwaukee Brewers (Sep 1)
Wrigley Field · Lakeview
From $22
Regular-season home game against Milwaukee Brewers at Wrigley Field.
Sep9
Sports
Cubs vs. Cincinnati Reds (Sep 9)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Sep10
Sports
Cubs vs. Cincinnati Reds (Sep 10)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Sep11
Sports
Cubs vs. Cincinnati Reds (Sep 11)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Sep12
Sports
Cubs vs. Cincinnati Reds (Sep 12)
Wrigley Field · Lakeview
From $22
Regular-season home game against Cincinnati Reds at Wrigley Field.
Sep14
Sports
Cubs vs. Baltimore Orioles (Sep 14)
Wrigley Field · Lakeview
From $22
Regular-season home game against Baltimore Orioles at Wrigley Field.
Sep15
Sports
Cubs vs. Baltimore Orioles (Sep 15)
Wrigley Field · Lakeview
From $22
Regular-season home game against Baltimore Orioles at Wrigley Field.
Sep16
Sports
Cubs vs. Baltimore Orioles (Sep 16)
Wrigley Field · Lakeview
From $22
Regular-season home game against Baltimore Orioles at Wrigley Field.
Sep17
Sports
Cubs vs. New York Mets (Sep 17)
Wrigley Field · Lakeview
From $22
Regular-season home game against New York Mets at Wrigley Field.
Sep18
Sports
Cubs vs. New York Mets (Sep 18)
Wrigley Field · Lakeview
From $22
Regular-season home game against New York Mets at Wrigley Field.
Sep19
Sports
Cubs vs. New York Mets (Sep 19)
Wrigley Field · Lakeview
From $22
Regular-season home game against New York Mets at Wrigley Field.
Apr3
Sports
White Sox vs. Milwaukee Brewers (Apr 3)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Milwaukee Brewers at Rate Field.
Apr4
Sports
White Sox vs. Milwaukee Brewers (Apr 4)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Milwaukee Brewers at Rate Field.
May17
Sports
White Sox vs. Cleveland Guardians (May 17)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Cleveland Guardians at Rate Field.
May18
Sports
White Sox vs. Cleveland Guardians (May 18)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Cleveland Guardians at Rate Field.
May19
Sports
White Sox vs. Cleveland Guardians (May 19)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Cleveland Guardians at Rate Field.
May28
Sports
White Sox vs. Seattle Mariners (May 28)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Seattle Mariners at Rate Field.
May29
Sports
White Sox vs. Seattle Mariners (May 29)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Seattle Mariners at Rate Field.
May30
Sports
White Sox vs. Seattle Mariners (May 30)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Seattle Mariners at Rate Field.
May31
Sports
White Sox vs. Tampa Bay Rays
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Tampa Bay Rays at Rate Field.
Jun18
Sports
White Sox vs. Minnesota Twins (Jun 18)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Minnesota Twins at Rate Field.
Jun19
Sports
White Sox vs. Minnesota Twins (Jun 19)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Minnesota Twins at Rate Field.
Jun20
Sports
White Sox vs. Minnesota Twins (Jun 20)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Minnesota Twins at Rate Field.
Jun21
Sports
White Sox vs. Texas Rangers (Jun 21)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Texas Rangers at Rate Field.
Jun22
Sports
White Sox vs. Texas Rangers (Jun 22)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Texas Rangers at Rate Field.
Jun23
Sports
White Sox vs. Texas Rangers (Jun 23)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Texas Rangers at Rate Field.
Jun24
Sports
White Sox vs. Kansas City Royals (Jun 24)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Kansas City Royals at Rate Field.
Jun25
Sports
White Sox vs. Kansas City Royals (Jun 25)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Kansas City Royals at Rate Field.
Jun26
Sports
White Sox vs. Kansas City Royals (Jun 26)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Kansas City Royals at Rate Field.
Jun27
Sports
White Sox vs. Kansas City Royals (Jun 27)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Kansas City Royals at Rate Field.
Jul9
Sports
White Sox vs. Arizona Diamondbacks (Jul 9)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Arizona Diamondbacks at Rate Field.
Jul10
Sports
White Sox vs. Arizona Diamondbacks (Jul 10)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Arizona Diamondbacks at Rate Field.
Jul11
Sports
White Sox vs. Arizona Diamondbacks (Jul 11)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Arizona Diamondbacks at Rate Field.
Aug9
Sports
White Sox vs. Boston Red Sox (Aug 9)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Boston Red Sox at Rate Field.
Aug10
Sports
White Sox vs. Boston Red Sox (Aug 10)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Boston Red Sox at Rate Field.
Aug11
Sports
White Sox vs. Boston Red Sox (Aug 11)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against Boston Red Sox at Rate Field.
Sep24
Sports
White Sox vs. San Diego Padres (Sep 24)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against San Diego Padres at Rate Field.
Sep25
Sports
White Sox vs. San Diego Padres (Sep 25)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against San Diego Padres at Rate Field.
Sep26
Sports
White Sox vs. San Diego Padres (Sep 26)
Rate Field · Armour Square / Bridgeport
From $20
Regular-season home game against San Diego Padres at Rate Field.
Sep25
Food & Drink
Oktoberfest Chicago (Downtown Oak Park)
Marion St. (Lake St. to North Blvd.) · Oak Park, IL (western suburb)
Free
A free two-day Bavarian street party on Marion Street — craft beer and wine, live oompah-adjacent music, and a kids' garden that keeps it a genuine family stop rather than just another beer tent. Smaller and easier to actually move around in than the big-name Oktoberfests downtown.
⚠ Located in Oak Park, a western suburb, not the city proper.
Oct9
Music & Nightlife
Tito Nieves: 50 Años La Historia Continúa
Copernicus Center · Jefferson Park
From $65
The 'King of Salsa Romantica' marks 50 years in the business at the Copernicus Center's ornate old theater — still the voice behind 'I Like It Like That' decades on, and a genuine crossover name rather than a niche booking.
Oct31
Halloween & Fall Seasonal
Haunted Halloween Ball
Congress Plaza Hotel · South Loop
From $20
A 21+ costume gala inside a hotel USA Today has called one of the most haunted in the world — 20,000 square feet of ballroom turned into an 'abandoned hotel run by zombies,' with a DJ, theatrical performers, and a $2,000 costume contest. Real production value, not just a bar with cobwebs taped up.
Oct3
Music & Nightlife
Best of iO Improv (45th Anniversary)
iO Theater · Lincoln Park
Not listed
Two teams of top iO improvisers run through classic house forms — the Living Room, Weirdass, Shotgun — built around 'The Dream,' a surreal bit spun live from an audience member's own interview. Marks 45 years of the theater that trained half the comedians you already know.
Dec6
Music & Nightlife
Jamila Woods: 10 Years of HEAVN
Thalia Hall · Pilsen
From $51
A hometown finale for the tour marking a decade since HEAVN, the Chicago poet-singer's breakout debut — still one of the sharpest, most specifically-Chicago records to come out of this city's scene. Limited-edition signed vinyl on offer for anyone who wants more than a ticket stub out of the night.
Dec6
Family & Free Community
Hyde Park Holly-Day
Throughout Hyde Park · Hyde Park
Free
The University of Chicago's own neighborhood holiday block party — ice carving demos, photos with Santa, a live reindeer and sleigh, and free holiday-craft stops scattered around the neighborhood. Genuinely free, genuinely low-key, a good alternative to the downtown holiday crowds.
⚠ 2026 date not yet formally confirmed — based on the event's early-December pattern (2025 ran Sat Dec 6).
Oct3
Food & Drink
Cider and Ale Festival at The Morton Arboretum
The Morton Arboretum · Lisle
From $45 (members) / $55 (general)
Sixty-plus ciders and beers from more than 30 regional makers, poured right along the Arboretum's fall-color trails instead of a parking lot — a genuinely pretty way to day-drink outdoors. General admission gets 20 three-ounce tastings and a souvenir glass; go early if you want the trees before the crowd shows up.
Oct5
Music & Nightlife
Journey: Final Frontier Tour
United Center · Near West Side
From $120
Fifty-plus years in and Journey is billing this one as a farewell run — no opener, two full sets with an intermission, and a setlist that reportedly digs into songs the band hasn't played live in decades alongside the stadium anthems everyone already knows by heart. If 'Don't Stop Believin'' has ever talked you through a bad week, this is the night to say thanks in person.
Nov24
Music & Nightlife
John Summit: CTRL/Escape Arena Tour
United Center · Near West Side
From $21
A hometown DJ filling the same arena the Bulls play in is a genuine story — Summit built his following on Twitch livestreams and Chicago house-scene roots before this became an arena tour. Two nights (Nov 24 and 25) with the first trending toward a sellout, so this is the one to move on early if you're going.
Nov15
Arts & Culture
Beatriz González: In Series and Full Color
Art Institute of Chicago · Loop
$32 non-resident / $20 resident; members free
Six decades of a Colombian painter turning tabloid photos and government portraits into flat, garish, unmistakably pop-inflected prints — sharper political commentary than the candy colors let on. This is the first Chicago retrospective dedicated to her drawings and prints, more than 80 works deep, opening the same year she died.
Oct31
Halloween & Fall Seasonal
Slightly Spooky Saturday
Navy Pier · Streeterville
Free
Free, indoors-and-out trick-or-treating along the whole Pier — 30-plus candy stops, aerial performers, a Dia de los Muertos art market, and a Dog Costume Contest at Harry Caray's for anyone whose real motivation is the dog. Good weather-proof option if Halloween weekend turns into a Chicago-in-October surprise.
Dec12
Music & Nightlife
Temples: The BLISS Tour
Thalia Hall · Pilsen
From $57
British psych-rock lifers Temples built a whole sound out of sounding like a lost 1968 acetate, and a decade-plus in, they still haven't run out of new ways to do it. GIFT opens, which means the fuzz starts early — get there on time.
Dec5
Family & Free Community
Downtown Evanston Holiday Light Celebration
Fountain Square · Evanston
Free
The North Shore's answer to the downtown tree-lighting crowds — Fountain Square fills up for carolers, Santa and Mrs. Claus, and one collective countdown before the whole square lights up at once. Small enough to actually enjoy with kids, close enough that you don't need a Loop parking garage.
⚠ Sources disagree on the exact 2026 date (Dec 5 vs. Dec 6) — confirm on the official site before planning around it.
About this section
Every event on this page is independently researched and verified against its own venue or organizer — not pulled from a syndicated listings feed. We update it continuously as new dates get confirmed and old ones pass, and we'd rather flag an unconfirmed date honestly than guess. Suburbs are included alongside the city. Missing something, or spot an error? Let us know.
