Festivals & Street Fairs Events in Chicago

37 real events — independently sourced, no listings dumps.

Maxwell Street Market

Maxwell St. (Halsted to Union)Sun Sept 13 & Sun Oct 4, 2026Free

Randolph Street Market

1341 W. Randolph St.Sept 26–27, 2026$14 online/$15 door ($5–10 discounts)

Lincoln Square Ravenswood Apple Fest

N. Lincoln Ave (Sunnyside to Lawrence)Fri Oct 2 (3–7PM), Sat–Sun Oct 3–4 (9AM–6PM), 2026$5 suggested donation

Bank of America Chicago Marathon

Course through 29 neighborhoods, finish in Grant ParkSun Oct 11, 2026Free to spectate

Open House Chicago

170+ sites across 20+ neighborhoodsOct 17–18, 2026Free

Chicago Artisan Market – Fulton Market

Morgan MFG, 401 N. Morgan St.Sun Oct 18, 2026$8 advance / $10 door

One of a Kind Holiday Show

The Mart (222 Merchandise Mart Plaza, 7th Floor)Thu–Sun Dec 3–6, 2026$12–$80 depending on day/tier

Geneva Christmas Walk

Geneva Courthouse lawn & downtownFri Dec 4, 2026Free

Randolph Street Market: Holiday Market

1341 W. Randolph St. (Plumbers Union Hall)Sat–Sun Dec 12–13, 2026$14 online/$15 door (kids 12 & under free)

Renegade Craft Fair: Chicago Holiday Market

Bridgeport Art CenterFri–Sun Dec 18–20, 2026Free

Chicago Boat, RV & Sail Show

Donald E. Stephens Convention CenterWed Feb 3 – Sun Feb 7, 2027Not listed — tickets online, price TBA

Chicago Chinatown Lunar New Year Parade

Wentworth Ave. (24th St. to Cermak)Sun Feb 14, 2027Free

Chicago St. Patrick's Day Parade & River Dyeing

Columbus Drive (Balbo Dr. to Monroe St.); river dyeing near the Columbus Dr. bridgeExpected Sat March 13, 2027 (city hasn't formally confirmed yet — parade always lands the Saturday nearest March 17)Free

South Side Irish Parade

Western Ave. (103rd to 111th St.)Expected Sun March 14, 2027 (Sunday before St. Patrick's Day — city hasn't formally confirmed the 2027 date yet)Free

Polish Constitution Day Parade

Columbus Dr.Expected Sat May 1, 2027 (Saturday closest to May 3 — 2027 dates not yet confirmed)Free

Sueños Music Festival

Grant ParkSat–Sun May 29–30, 2027From $279 (2-day GA)

Do Division Street Fest

Division St. (Ashland to Leavitt)Expected Sat–Mon May 29–31, 2027 (Memorial Day weekend — 2027 dates not yet formally confirmed)Free (suggested $10 donation)

57th Street Art Fair

57th St. (Kimbark to Kenwood Ave.)Expected Sat–Sun June 5–6, 2027 (2027 dates not yet confirmed — pattern-based estimate)Free

Andersonville Midsommarfest

Clark St. (Andersonville)Expected Fri–Sun June 11–13, 2027 (second weekend of June — 2027 dates not yet confirmed)Free ($10 suggested donation)

Wells Street Art Festival

Wells St. (North Ave. to Division St.)Expected Sat–Sun June 12–13, 2027 (2027 dates not yet confirmed — pattern-based estimate)Free (gate donations suggested)

Puerto Rican People's Day Parade & Festival

Division St. & Campbell Ave. (Paseo Boricua)Expected Sat June 12, 2027 (second Saturday of June — 2027 dates not yet confirmed)Free

Chicago Pride Parade

Broadway & Halsted (Lakeview/Boystown route)Sun June 27, 2027Free

Northalsted Market Days

Halsted St. (Northalsted)Expected Fri–Sun Aug 6–8, 2027 (2026 ran Aug 7–9 — 2027 dates not yet formally confirmed)Free (suggested $20/day donation)

Bud Billiken Parade & Festival

Dr. Martin Luther King Jr. Drive (35th to 55th St.)Sat Aug 14, 2027Free to watch (VIP seating available)

Chicago Air & Water Show

North Avenue Beach / lakefrontExpected Sat–Sun Aug 21–22, 2027 (third weekend of August — 2027 dates not yet formally confirmed)Free

Argyle Lunar New Year Celebration

Argyle St. & Sheridan Rd.Expected mid-to-late Feb 2027 (2026 ran Feb 21 — exact 2027 date not yet announced)Free

Chicago Auto Show

McCormick PlaceSat Feb 13 – Sun Feb 21, 2027$20 adults / $15 seniors & kids 4–12; free under 3 (weekday & first-responder discounts available)

Chicago Blues Festival

Millennium ParkExpected early June 2027 (2027 dates not yet formally confirmed)Free

Chicago Flower & Garden Show

Navy Pier (Festival Hall)March 7–15, 2027 (one source said March 18–22 — confirm exact dates closer to the show)$20 adult / $5 child (ages 5–12)

Chinatown Summer Fair

Wentworth Ave. (Cermak to 24th Pl.)Expected late July 2027 (2026 ran Jul 25–26 — 2027 dates not yet formally announced)Free

Christkindlmarket Aurora

RiverEdge ParkFri Nov 20 – Thu Dec 24, 2026Free admission

Christkindlmarket Chicago at Daley Plaza

Daley Plaza (50 W. Washington St.)Nov 20 – Dec 24, 2026Free admission

Christkindlmarket Wrigleyville

Gallagher Way (3635 N. Clark St.)Nov 20 – Dec 31, 2026Free admission

Fiesta del Sol

Ashland & Cermak to Morgan & CermakExpected late July 2027 (2026 ran Jul 23–26 — 2027 dates not yet formally announced)Free

Logan Square Farmers Market (Winter, Indoor)

Avondale Collective, 2800 N. Milwaukee Ave.Saturdays, Dec 2026 – March 2027Free

Neighborhood Farmers Markets (recurring)

Daley Plaza; Jarvis Square; Andersonville; SOAR StreetervilleThrough late Oct 2026 (Thu/Fri/varies by site)Free

World Music Festival Chicago

Chicago Cultural Center, Millennium Park, Navy Pier, Old Town School, Nat'l Museum of Mexican Art, Logan Center, Pritzker PavilionSept 25 – Oct 4, 2026Free