Stumblday accountsFor organizers and followers
Stumblday's day-by-day guide to Chicago for the next seven days, Friday, October 2 through Thursday, October 8: the best bet for every day, including Lincoln Square Ravenswood Apple Fest 2026, Doja Cat – Tour Ma Vie World Tour and Chicago Bears vs. New York Jets, then each day's shortlist — hand-checked against organizers' own pages.
Friday, Oct 2 – Thursday, Oct 8
Lincoln Avenue (Lawrence to Sunnyside), Lincoln Squarew_lemay · CC BY-SA 2.0 · Wikimedia CommonsLincoln Square's 39th Apple Fest: Midwest orchard apples and cider, cider donuts and taffy apples, 100+ vendors and live music on a closed-off Lincoln Avenue.
Lincoln Avenue (Lawrence to Sunnyside), Lincoln Squarew_lemay · CC BY-SA 2.0 · Wikimedia CommonsLincoln Square's 39th Apple Fest: Midwest orchard apples and cider, cider donuts and taffy apples, 100+ vendors and live music on a closed-off Lincoln Avenue.
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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 the United Center.
United Center, Pilsen, West Town & the West SideAlacoolwiki · CC BY-SA 4.0 · Wikimedia CommonsLE Sserafim brings the Pureflow Tour to the United Center.
Add to calendarBill Burr headlines The Chicago Theatre for a weekend stand-up set.
Downstairs Theatre At Steppenwolf Theatre – ChicagoTopdog/Underdog – Chicago is listed for Chicago this weekend.
Downstairs Theatre At Steppenwolf Theatre – ChicagoTopdog/Underdog – Chicago is listed for Chicago this weekend.
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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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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United Center, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsDoja Cat brings the Tour Ma Vie World Tour to the United Center.
United Center, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsDoja Cat brings the Tour Ma Vie World Tour to the United Center.
Add to calendarThe Chicks bring Taking the Long Way to the Auditorium Theatre.
The Chicks bring Taking the Long Way to the Auditorium Theatre.
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The University of Chicago, Hyde ParkNdshankar · CC BY-SA 4.0 · Wikimedia CommonsThe South Side Science Festival fills the University of Chicago with hands-on discovery.
The University of Chicago, Hyde ParkNdshankar · CC BY-SA 4.0 · Wikimedia CommonsThe South Side Science Festival fills the University of Chicago with hands-on discovery.
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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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CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOperation Mincemeat brings its wartime musical caper to the CIBC Theatre.
CIBC Theatre, 18 West Monroe, Downtown, the Loop & West LoopOperation Mincemeat brings its wartime musical caper to 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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Soldier Field, Museum Campus, Downtown, the Loop & West LoopPhoto by Joon Han Contact: onejoon@hotmail.com · CC BY-SA 3.0 · Wikimedia CommonsThe Bears host the Jets at Soldier Field in a Sunday NFL matchup.
Soldier Field, Museum Campus, Downtown, the Loop & West LoopPhoto by Joon Han Contact: onejoon@hotmail.com · CC BY-SA 3.0 · Wikimedia CommonsThe Bears host the Jets at Soldier Field in a Sunday NFL matchup.
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Humboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & BucktownSteven Kevil · CC BY-SA 4.0 · Wikimedia CommonsThe Global Peace Party brings World Music Festival Chicago to Humboldt Park.
Humboldt Park Fieldhouse (outdoor), Humboldt Park, Logan Square, Wicker Park & BucktownSteven Kevil · CC BY-SA 4.0 · Wikimedia CommonsThe Global Peace Party brings World Music Festival Chicago to Humboldt Park.
Add to calendarFriday at 5pm, one email. Unsubscribe anytime.
Maxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopMaxwell Street Market closes its season with food, vendors and live music.
Maxwell Street between S. Halsted St. and S. Union Ave., Downtown, the Loop & West LoopMaxwell Street Market closes its season with food, vendors and live music.
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Cahn Auditorium, EvanstonMjgrygleski · CC BY-SA 4.0 · Wikimedia CommonsEric Idle pairs stories with a Monty Python singalong at Cahn Auditorium.
Cahn Auditorium, EvanstonMjgrygleski · CC BY-SA 4.0 · Wikimedia CommonsEric Idle pairs stories with a Monty Python singalong at Cahn Auditorium.
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Metro Chicago, Lincoln Park, Lakeview & WrigleyvilleJoi Ito · CC BY 2.0 · Wikimedia CommonsBright Eyes takes the Metro stage for a Chicago concert.
Metro Chicago, Lincoln Park, Lakeview & WrigleyvilleJoi Ito · CC BY 2.0 · Wikimedia CommonsChicago Stars FC take on Denver Summit FC at Martin Stadium in Evanston.
Chicago Stars FC take on Denver Summit FC at Martin Stadium in Evanston.
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Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsSeventy-five giant pumpkins, live carving and performers light a three-night garden walk.
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsSeventy-five giant pumpkins, live carving and performers light a three-night garden walk.
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Stolp Island Theatre, Aurora, Far SuburbsMillion Dollar Quartet is listed for Chicago this weekend.
Stolp Island Theatre, Aurora, Far Suburbs
McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsFree and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
McCormick Place, North Building, Hall B1, Near South Side, Downtown, the Loop & West LoopWarren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia CommonsFree and open to anyone: marathon bib pickup and the whole race-weekend trade floor.
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Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsThe citywide fashion calendar spans markets, runway shows and store events.
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsThe citywide fashion calendar spans markets, runway shows and store events.
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Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareA Strange Loop is listed for Chicago this weekend.
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia CommonsART on THE Mart is listed for Chicago this weekend.
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopChris Rycroft from Madison, Wisconsin, United States · CC BY 2.0 · Wikimedia Commons