Stumblday's hand-checked ranking of the best things to do in Chicago the weekend of Oct 2–4, 2026: 274 picks, refreshed weekly. Concerts, festivals, art, markets, and free outdoor events.
274 picks · checked Sep 21
Soldier Field, Downtown, the Loop & West LoopPhoto by Joon Han Contact: onejoon@hotmail.com · CC BY-SA 3.0 · Wikimedia CommonsThe Bears face the Jets at Soldier Field at noon.
Soldier Field, Downtown, the Loop & West LoopPhoto by Joon Han Contact: onejoon@hotmail.com · CC BY-SA 3.0 · Wikimedia Commons
United Center, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsDoja Cat brings her Tour Ma Vie World Tour to United Center.
United Center, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsDoja Cat brings her Tour Ma Vie World Tour to United Center.
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United Center, Pilsen, West Town & the West SideAlacoolwiki · CC BY-SA 4.0 · Wikimedia CommonsLE Sserafim brings the Pureflow Tour to United Center on the West Side.
United Center, Pilsen, West Town & the West SideAlacoolwiki · CC BY-SA 4.0 · Wikimedia CommonsLE Sserafim brings the Pureflow Tour to United Center on the West Side.
Add to calendarBill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
Bill Burr, host of the Monday Morning Podcast and creator of specials including Paper Tiger, takes his stand-up to the Chicago Theatre.
Add to calendarIt lands the Friday before, plus every Friday until then. Unsubscribe anytime.
Lincoln Avenue, Lawrence to Sunnyside, Lincoln Square, Andersonville, Uptown & Lincoln Squarew_lemay · CC BY-SA 2.0 · Wikimedia CommonsBuild an autumn outing around apple treats, neighborhood vendors and live music along Lincoln Avenue.
Lincoln Avenue, Lawrence to Sunnyside, Lincoln Square, Andersonville, Uptown & Lincoln Squarew_lemay · CC BY-SA 2.0 · Wikimedia Commons7 added to calendar
Build an autumn outing around apple treats, neighborhood vendors and live music along Lincoln Avenue.
Add to calendarThe Chicks headline The Auditorium downtown for a single night.
The Chicks headline The Auditorium downtown for a single night.
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The University of Chicago, Hyde Park, Bronzeville & the South SideNdshankar · CC BY-SA 4.0 · Wikimedia CommonsUChicago scientists run free hands-on demos, brain-bending challenges and a sub-zero science show.
The University of Chicago, Hyde Park, Bronzeville & the South SideNdshankar · CC BY-SA 4.0 · Wikimedia CommonsUChicago scientists run free hands-on demos, brain-bending challenges and a sub-zero science show.
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Humboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & BucktownSteven Kevil · CC BY-SA 4.0 · Wikimedia CommonsThe festival ends with a free outdoor afternoon: Dogo du Togo, El Laberinto del Coco and more.
Humboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & BucktownSteven Kevil · CC BY-SA 4.0 · Wikimedia CommonsThe festival ends with a free outdoor afternoon: Dogo du Togo, El Laberinto del Coco and more.
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Maxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopMaxwell Street's free open-air market returns with vendors, food and music.
Maxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopMaxwell Street's free open-air market returns with vendors, food and music.
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Downstairs Theatre At Steppenwolf Theatre – Chicago, Lincoln Park, Lakeview & Wrigleyvillevictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsA play about brotherhood, identity and survival in Steppenwolf's intimate Downstairs Theatre.
Downstairs Theatre At Steppenwolf Theatre – Chicago, Lincoln Park, Lakeview & Wrigleyvillevictorgrigas · CC BY-SA 3.0 · Wikimedia CommonsA play about brotherhood, identity and survival in Steppenwolf's intimate Downstairs Theatre.
Add to calendarCollege football at Ryan Field in Evanston, with a food festival that starts at 5pm.
College football at Ryan Field in Evanston, with a food festival that starts at 5pm.
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Credit Union 1 Amphitheatre, Far SuburbsFuerza Regida opens the fall leg of its This Is Our Dream Tour at Credit Union 1 Amphitheatre.
Credit Union 1 Amphitheatre, Far SuburbsFuerza Regida opens the fall leg of its This Is Our Dream Tour at Credit Union 1 Amphitheatre.
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Metro Chicago, Lincoln Park, Lakeview & WrigleyvilleJoi Ito · CC BY 2.0 · Wikimedia CommonsBright Eyes plays Metro Chicago in Lakeview evening.
Metro Chicago, Lincoln Park, Lakeview & WrigleyvilleJoi Ito · CC BY 2.0 · Wikimedia Commons
Riviera Theatre, Andersonville, Uptown & Lincoln SquarePaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsMastodon brings the Poisonous Weapons Tour to the Riviera Theatre.
Riviera Theatre, Andersonville, Uptown & Lincoln SquarePaul R. Burley · CC BY-SA 4.0 · Wikimedia CommonsMastodon brings the Poisonous Weapons Tour to the Riviera Theatre.
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Downtown Highwood, Highwood, Far SuburbsAdam Moss · CC BY-SA 2.0 · Wikimedia CommonsThe North Shore's big fall street fest: pumpkin walls, carving, a carnival and two music stages.
Downtown Highwood, Highwood, Far SuburbsAdam Moss · CC BY-SA 2.0 · Wikimedia CommonsThe North Shore's big fall street fest: pumpkin walls, carving, a carnival and two music stages.
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The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleDJ Shadow celebrates 30 years of his debut album Endtroducing at The Vic Theatre.
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleDJ Shadow celebrates 30 years of his debut album Endtroducing at The Vic Theatre.
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CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOperation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOperation Mincemeat turns a bizarre Second World War deception plot into a musical comedy at the CIBC Theatre.
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Schiller Woods East, Grove 13, Schiller Woods, Logan Square, Wicker Park & BucktownGanesha811 · CC BY-SA 4.0 · Wikimedia CommonsChicago's oldest powwow, running since 1953, with Grand Entries at 11 and 3.
Schiller Woods East, Grove 13, Schiller Woods, Logan Square, Wicker Park & BucktownGanesha811 · CC BY-SA 4.0 · Wikimedia CommonsChicago's oldest powwow, running since 1953, with Grand Entries at 11 and 3.
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Cahn Auditorium, Evanston, Evanston & Oak ParkEric Idle talks and leads a singalong at Cahn Auditorium in Evanston afternoon.
Cahn Auditorium, Evanston, Evanston & Oak ParkEric Idle talks and leads a singalong at Cahn Auditorium in Evanston afternoon.
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Humboldt Park, Logan Square, Wicker Park & Bucktownpublic-domain postcard scan · public domain · Wikimedia CommonsA Humboldt Park 5K ends with a daytime concert featuring Diplo and Felix da Housecat.
Humboldt Park, Logan Square, Wicker Park & Bucktownpublic-domain postcard scan · public domain · Wikimedia CommonsA Humboldt Park 5K ends with a daytime concert featuring Diplo and Felix da Housecat.
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Smart Museum of Art, Hyde Park, Bronzeville & the South SideMichael Barera · CC BY-SA 4.0 · Wikimedia CommonsA free afternoon opening for three new shows, including teamLab and Nina Chanel Abney.
Smart Museum of Art, Hyde Park, Bronzeville & the South SideMichael Barera · CC BY-SA 4.0 · Wikimedia CommonsA free afternoon opening for three new shows, including teamLab and Nina Chanel Abney.
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Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsMäkelä leads the orchestra through Mahler's Ninth at Orchestra Hall.
Orchestra Hall, Symphony Center, Downtown, the Loop & West LoopI'm nonpartisan · CC BY-SA 3.0 · Wikimedia CommonsMäkelä leads the orchestra through Mahler's Ninth at Orchestra Hall.
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Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFree harvest fun at the zoo: s'mores, pro pumpkin carvers, pick-your-own pumpkins and live music.
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFree harvest fun at the zoo: s'mores, pro pumpkin carvers, pick-your-own pumpkins and live music.
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Multiple Chicago venuesw_lemay · CC BY-SA 2.0 · Wikimedia CommonsFollow free international music performances across Chicago, from an afternoon park gathering to late club shows and a closing outdoor celebration.
Multiple Chicago venuesw_lemay · CC BY-SA 2.0 · Wikimedia CommonsFollow free international music performances across Chicago, from an afternoon park gathering to late club shows and a closing outdoor celebration.
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