Stumblday calendar · Chicago

Free things to do in Chicago

Free events across Chicago each weekend: festivals, outdoor shows, talks and markets, checked against the organizers' pages.

Hand-picked by Stumblday. Pulled from each week’s Chicago board, where every listing is checked against the organizer’s own page.

Upcoming · 35

Friday, Oct 2

3 PM Lincoln Square Ravenswood Apple Fest 2026 Lincoln Avenue (Lawrence to Sunnyside), Lincoln Square · Free

4 PM The Great Highwood Pumpkin Festival Downtown Highwood, Highwood, Far Suburbs · Free

4 PM 60th Annual St. Benedict Oktoberfest St. Benedict Parish, North Center, Lincoln Park, Lakeview & Wrigleyville · Free

5 PM Harmony Fest Featuring the Taste of Arlington Heights Harmony Park, Arlington Heights, Far Suburbs · Free

5 PM Sauced Night Market HOSTE, Pilsen, West Town & the West Side · Free

7 PM Campfire Horrors: The Rocky Horror Picture Show Northerly Island Park, South Loop, Downtown, the Loop & West Loop · Free

9 PM World Music Festival Chicago: Grupo Rebolu and Radio Free Honduras Chop Shop + 1st Ward Events, Wicker Park · Free

Saturday, Oct 3

9 AM South Side Science Festival The University of Chicago, Hyde Park · Free

11 AM The Great Art Tailgate with Bad at Sports Museum of Contemporary Art Chicago, Streeterville, Downtown, the Loop & West Loop · Free

11 AM Bollywood Groove Indian Dances & Stories at Holstein Bucktown · Free

12 PM Block Club Chicago Block Party Half Acre Beer Co. — Balmoral, Bowmanville, Andersonville, Uptown & Lincoln Square · Free

1 PM Bernice Wolnik Poetry at the Polish Museum of America West Town · Free

1:30 PM Fall Fest Four Seasons, Lombard, Far Suburbs · Free

2 PM Smart Museum Fall Exhibition Opening Smart Museum of Art, Hyde Park · Free

2 PM World Music Festival Chicago: The Klezmatics and Los Vega Beverly Arts Center, Beverly, Hyde Park, Bronzeville & the South Side · Free

7 PM Campfire Horrors: The Addams Family at Loyola Park Rogers Park, Andersonville, Uptown & Lincoln Square · Free

9 PM World Music Festival Chicago: Saha Gnawa and Chamni Sripraram Thai Music Ensemble Sleeping Village, Avondale, Lincoln Park, Lakeview & Wrigleyville · Free

Sunday, Oct 4

10 AM Maxwell Street Market – season finale Maxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West Loop · Free

12 PM World Music Festival Chicago: Global Peace Party Humboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & Bucktown · Free

12 PM 2026 Final Auditions Lyric Opera House, Loop · Free

Thursday, Oct 8

10 AM Abbott Health & Fitness Expo McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West Loop · Free

Friday, Oct 9

5 PM Transilience: Chicago Trans Pride Festival at Eckhart Eckhart (Bernard) Park, West Town, Logan Square, Wicker Park & Bucktown · Free

6 PM The Heart of the Story at Douglass Douglass Park, North Lawndale, Pilsen, West Town & the West Side · Free

6 PM Apple Bottoms x Chicago Three Cities Social Club – Wicker Park, Wicker Park · Free

Saturday, Oct 10

10 AM Really Really Free Market AIDS Garden Chicago, Lincoln Park, Lakeview & Wrigleyville · Free

11 AM Family Day | Warmups Museum of Contemporary Art Chicago, Streeterville, Downtown, the Loop & West Loop · Free

11 AM Chicago Zine Fest 2026 Harold Washington Library Center, Loop · Free

11 AM Indigenous Peoples' Day Celebration at Harrison Harrison (Carter) Park, Pilsen · Free

11 AM Oktoberfestiversary Begyle Brewing and Dovetail Brewery, Ravenswood, Andersonville, Uptown & Lincoln Square · Free

11 AM Healing Arts Chicago Summit Malcolm X College, Near West Side, Pilsen, West Town & the West Side · Free

Sunday, Oct 11

3 PM Chicago Latino Dance Festival at Humboldt Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & Bucktown · Free

4 PM teamLab & Allison Martino in Conversation Smart Museum of Art, Hyde Park · Free

Monday, Oct 12

9:30 AM Chicago History Museum Illinois Resident Free Day Chicago History Museum, Lincoln Park · Free

10 AM Indigenous Peoples' Day Free Admission at Gichigamiin Indigenous Nations Museum Gichigamiin Indigenous Nations Museum, Evanston · Free

7:30 PM Indigenous Peoples' Day featuring Colectivo Sayba, Tamanaco Tambor & Trio Axol Old Town School of Folk Music, Lincoln Square · Free