Food & Drink Events in Chicago

27 real events — independently sourced, no listings dumps.

Chi Food Truck Fest (weekly)

Daley PlazaFridays Sept 4, 11, 18, 25 & Oct 2, 2026Free entry (pay per item)

St. Alphonsus Oktoberfest (25th Annual)

1429 W Wellington AveSept 25–27, 2026$10 Fri/Sat; $5 suggested donation Sun

Jerk, Seafood & Vegan Fest (JSVFest) / African-Caribbean Int'l Festival

Union Park (per JSVFest listing) — one source says Washington ParkSept 25–27, 2026Not listed

Oktoberfest Chicago (Downtown Oak Park)

Marion St. (Lake St. to North Blvd.)Fri–Sat Sept 25–26, 2026Free

All You Can Eataly: Septemberfest

Eataly ChicagoFri Sept 26, 2026GA $150.99; VIP $210.01

2026 Chicago Top Shelf Tequila and Whiskey Tasting Festival

Downtown Chicago (exact address via ticket link)Sat Sept 26, 2026Not listed (limited to 299 guests)

WingOut Chicago

Gallagher WaySat–Sun Sept 26–27, 2026From $20 GA / $109 VIP

Andersonville Fall Wine Walk

Clark St., Balmoral & Summerdale (Andersonville)Sun Sept 27, 2026$40 per ticket

Cider and Ale Festival at The Morton Arboretum

The Morton ArboretumSat Oct 3, 2026From $45 (members) / $55 (general)

Oktoberfestiversary (Dovetail x Begyle)

Shared lot, Dovetail Brewery & Begyle BrewingOct 10–11, 2026$5 suggested donation (benefits food pantry)

West Pullman Food Truck Festival

821 W. 115th St.Sat Oct 10, 2026Not listed

Lincoln Park Wine Fest (10th Anniversary)

Jonquil ParkSun Oct 11, 2026Not listed (21+ only)

Whisky Jewbilee Chicago 2026

Artifact EventsThu Oct 15, 2026Not listed

International Wine and Spirits Trade Show

Navy PierOct 18–19, 2026Not listed (trade-focused)

Chicago Pizza Summit (10th Anniversary)

Venue TBATue Nov 3, 2026Not yet announced

Elf'd Up

Stretch Bar & GrillOpens Fri Nov 7, 2026 (through early January 2027 — sources disagree on the exact closing date; confirm before you go)No cover (pay per drink/item)

FOBAB (Festival of Wood & Barrel-Aged Beer)

Credit Union 1 ArenaFri–Sat Nov 13–14, 2026$85 per session

Simply Ina: An Evening with Ina Garten

Auditorium TheatreThu Nov 19, 2026From $98

Clark Street Cookie Crawl

Clark St. (Fullerton to Diversey)Sun Dec 6, 2026$30 general / $45 boozy

Ribfest Chicago

Lincoln Ave. (Irving Park Rd. to Hutchinson)Expected Fri–Sun June 4–6, 2027 (2026 ran June 5–7 — 2027 dates not yet formally confirmed)$10 suggested donation

Windy City Smokeout

United Center (outdoor lots)Thu–Sun July 8–11, 2027Not yet listed — check windycitysmokeout.com

Chicago Beer Festival

Field MuseumExpected late Feb 2027 (2026 ran Feb 28 — 2027 date not yet formally confirmed)$60 general / $75 early admission

Chicago Restaurant Week 2027

Citywide — participating restaurantsTBA — 2027 dates not yet announced (2026 ran Jan 23 – Feb 8)Fixed-price menus, set per restaurant

Fulton Market Oktoberfest (Oktoberfest Nation)

171 N Peoria StSept 17 – Oct 24/26, 2026Ticketed, price TBD

James Beard Awards Week

Lyric Opera House & venues citywideExpected mid-June 2027 (exact 2027 date not yet announced — 2026 ceremony was June 15)Ceremony sold out to industry; satellite events $175+

Oktoberfest at The Northman Beer & Cider Garden

233 E RiverwalkSept 18 – Oct 4, 2026Not listed

Taste of Randolph

Randolph St. (near 900 W.)Expected mid-to-late June 2027 (2026 ran June 19–21 — 2027 dates not yet confirmed)Free