#1
Sun, Oct 11, 2026 · 7:00pm
Olivia Rodrigo – The Unraveled Tour
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
One Weekend Only
Things to Do in Chicago on Columbus Day Monday, Oct 12
Stumblday's hand-checked ranking of the best things to do in Chicago on Columbus Day Monday, Oct 12: 89 picks, refreshed weekly.
89 picks · checked Sep 21
89 picks
#1Sun, Oct 11, 2026 · 7:00pm · One Weekend Only
Olivia Rodrigo – The Unraveled Tour
Pop star's arena tour opens its two-night Chicago stand, with Wolf Alice as special guest.
Add to calendar#2
Dearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopAlphaBeta135 · CC BY 4.0 · Wikimedia CommonsMonday, October 12, 2026; opening ceremony at 12 PM at Dearborn Street and Wacker Drive, then the parade steps off south on Dearborn to Van Buren
74th Annual Chicago Columbus Day Parade
Lou Gramm, Tony Danza and Cristiana Dell'Anna lead the march down Dearborn as grand marshals.
One Day Only
#2Monday, October 12, 2026; opening ceremony at 12 PM at Dearborn Street and Wacker Drive, then the parade steps off south on Dearborn to Van Buren · One Day Only
Dearborn Street, Wacker Drive to Van Buren Street, The Loop, Downtown, the Loop & West LoopAlphaBeta135 · CC BY 4.0 · Wikimedia Commons74th Annual Chicago Columbus Day Parade
Lou Gramm, Tony Danza and Cristiana Dell'Anna lead the march down Dearborn as grand marshals.
Add to calendar#3
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsSeptember 25–November 1, 2026; pumpkin patch open daily, live pumpkin carving weekends 10am–1pmFree
Fall Fest at Lincoln Park Zoo
Free harvest fun at the zoo: s'mores, pro pumpkin carvers, pick-your-own pumpkins and live music.
FreeLimited Run
#3September 25–November 1, 2026; pumpkin patch open daily, live pumpkin carving weekends 10am–1pm · Limited Run
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleJrbarc! · CC BY-SA 4.0 · Wikimedia CommonsFall Fest at Lincoln Park Zoo
Free harvest fun at the zoo: s'mores, pro pumpkin carvers, pick-your-own pumpkins and live music.
Add to calendar#4
United Center, Near West Side, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsMonday, October 12, 2026, 7:00 PMTickets via Ticketmaster
Olivia Rodrigo: The Unraveled Tour – Night Two
The second of two United Center nights, on the holiday, is the other shot at a top pop act.
Limited Run
#4Monday, October 12, 2026, 7:00 PM · Limited Run
United Center, Near West Side, Pilsen, West Town & the West SideUser:JeremyA · CC BY-SA 2.5 · Wikimedia CommonsOlivia Rodrigo: The Unraveled Tour – Night Two
The second of two United Center nights, on the holiday, is the other shot at a top pop act.
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#5
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:30pm
Topdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Limited Run
#5Fri, Oct 9, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Add to calendar#6
F1 Arcade, River North, Downtown, the Loop & West LoopOpen this weekend — recently opened
F1 Arcade
A newly opened River North bar with 61 driving simulators, plus brisket tacos and burgers.
Limited Run
#6Open this weekend — recently opened · Limited Run
F1 Arcade, River North, Downtown, the Loop & West LoopF1 Arcade
A newly opened River North bar with 61 driving simulators, plus brisket tacos and burgers.
Add to calendar#7
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsOctober 8–18, 2026 · Events at venues across Chicago
Chicago Fashion Week
The citywide fashion calendar spans markets, runway shows and store events.
Limited Run
#7October 8–18, 2026 · Events at venues across Chicago · Limited Run
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsChicago Fashion Week
The citywide fashion calendar spans markets, runway shows and store events.
Add to calendar#8
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#8September 11–October 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! — Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendar#9
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsMon, Oct 12, 2026 · 7:30pm
Simple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
One Day Only
#9Mon, Oct 12, 2026 · 7:30pm · One Day Only
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsSimple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
Add to calendar#10
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM$20 individual programs
Cinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
One Weekend Only
#10Sunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM · One Weekend Only
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleCinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
Add to calendar#11
Brookfield Zoo Chicago, Evanston & Oak ParkThrough Oct 25, 2026
BOO! at the Zoo
Brookfield Zoo's Halloween tradition brings festive décor and family-friendly surprises.
Limited Run
#11Through Oct 25, 2026 · Limited Run
Brookfield Zoo Chicago, Evanston & Oak ParkBOO! at the Zoo
Brookfield Zoo's Halloween tradition brings festive décor and family-friendly surprises.
Add to calendar#12
Chicago History Museum, Lincoln Park, Lakeview & WrigleyvilleGoldnpuppy · CC BY-SA 3.0 · Wikimedia CommonsMonday, October 12, 2026 · 9:30 AM–4:30 PMFree for Illinois residents
Chicago History Museum Illinois Resident Free Day
Illinois residents get free Monday access to the museum’s permanent and temporary shows.
FreeOne Day Only
#12Monday, October 12, 2026 · 9:30 AM–4:30 PM · One Day Only
Chicago History Museum, Lincoln Park, Lakeview & WrigleyvilleGoldnpuppy · CC BY-SA 3.0 · Wikimedia CommonsChicago History Museum Illinois Resident Free Day
Illinois residents get free Monday access to the museum’s permanent and temporary shows.
Add to calendar#13
Green Mill Cocktail Lounge, Uptown, Andersonville, Uptown & Lincoln SquareKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsSaturdays at 3pm (doors 1pm); no end date announcedFREE
The Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
FreeLimited Run
#13Saturdays at 3pm (doors 1pm); no end date announced · Limited Run
Green Mill Cocktail Lounge, Uptown, Andersonville, Uptown & Lincoln SquareKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsThe Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
Add to calendar#14
Abbey Farms, Aurora, Far SuburbsSeptember 19–November 1, 2026; September weekends 10 a.m.–6 p.m.; October Wed–Fri and Sun 10 a.m.–6 p.m., Sat 10 a.m.–10 p.m.$21 online or $23 at the gate…
Pumpkin Daze
Pumpkin Daze runs September 19–November 1 at Abbey Farms with a corn maze, pumpkins, family rides, games and food.
Limited Run
#14September 19–November 1, 2026; September weekends 10 a.m.–6 p.m.; October Wed–Fri and Sun 10 a.m.–6 p.m., Sat 10 a.m.–10 p.m. · Limited Run
Abbey Farms, Aurora, Far SuburbsPumpkin Daze
Pumpkin Daze runs September 19–November 1 at Abbey Farms with a corn maze, pumpkins, family rides, games and food.
Add to calendar#15
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleMonday, October 12, 2026 · 7 PM; post-film director Q&A$15 general admission
Begotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Limited Run
#15Monday, October 12, 2026 · 7 PM; post-film director Q&A · Limited Run
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleBegotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Add to calendar#16
Richard H. Driehaus Museum, River North, Downtown, the Loop & West LoopOctober 9, 2026 – April 18, 2027Adults $23
Emma Stebbins: Carving Out History
Emma Stebbins: Carving Out History
ArtLimited Run
#16October 9, 2026 – April 18, 2027 · Limited Run
Richard H. Driehaus Museum, River North, Downtown, the Loop & West Loop#17
Chicago Children’s Museum, Navy Pier, Downtown, the Loop & West LoopMonday, October 12, 2026 · 10 AM–3 PMMuseum admission applies
Indigenous People’s Day at Chicago Children’s Museum
A story lounge and native Illinois seed-ball activity mark Indigenous People’s Day.
One Day Only
#17Monday, October 12, 2026 · 10 AM–3 PM · One Day Only
Chicago Children’s Museum, Navy Pier, Downtown, the Loop & West LoopIndigenous People’s Day at Chicago Children’s Museum
A story lounge and native Illinois seed-ball activity mark Indigenous People’s Day.
Add to calendar#18
Northlight Theatre, Evanston, Evanston & Oak ParkSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Limited Run
#18September 9 – October 25, 2026 (extended) · Limited Run
Northlight Theatre, Evanston, Evanston & Oak ParkThe Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendar#19
Old Town School of Folk Music, Lincoln Square, Andersonville, Uptown & Lincoln SquareMonday, October 12, 2026, 7:30pmFree
Indigenous Peoples' Day featuring Colectivo Sayba, Tamanaco Tambor & Trio Axol
Indigenous Peoples' Day featuring Colectivo Sayba, Tamanaco Tambor & Trio Axol has enough weekend energy to earn a spot on the board.
FreeLimited Run
#19Monday, October 12, 2026, 7:30pm · Limited Run
Old Town School of Folk Music, Lincoln Square, Andersonville, Uptown & Lincoln SquareIndigenous Peoples' Day featuring Colectivo Sayba, Tamanaco Tambor & Trio Axol
Indigenous Peoples' Day featuring Colectivo Sayba, Tamanaco Tambor & Trio Axol has enough weekend energy to earn a spot on the board.
Add to calendar#20
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsAugust 19–October 18, 2026Tickets via Drury Lane box of…
The Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Limited Run
#20August 19–October 18, 2026 · Limited Run
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsThe Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Add to calendar#21
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 – November 8, 2026Tickets via Raven Theatre
A Strange Loop
A Strange Loop has enough weekend energy to earn a spot on the board.
Limited Run
#21October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#22
Chicago Cultural Center, The Loop, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsThrough Nov 8, 2026FREE
Tangible Sound: Arrival to a Higher Ground
DCASE's free flagship show in the Loop, open daily 10am to 5pm.
FreeLimited Run
#22Through Nov 8, 2026 · Limited Run
Chicago Cultural Center, The Loop, Downtown, the Loop & West LoopGrant Henninger · CC BY-SA 4.0 · Wikimedia CommonsTangible Sound: Arrival to a Higher Ground
DCASE's free flagship show in the Loop, open daily 10am to 5pm.
Add to calendar#23
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsMonday 7pm
Faust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Limited Run
#23Monday 7pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsFaust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Add to calendar#24
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopExtended through November 15, 2026; 75-minute timed performances
Theater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Limited Run
#24Extended through November 15, 2026; 75-minute timed performances · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopTheater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Add to calendar