#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 Sunday, Oct 11
Stumblday's hand-checked ranking of the best things to do in Chicago on Sunday, Oct 11: 130 picks, refreshed weekly.
130 picks · checked Sep 21
130 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
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsSunday, October 11, 2026, 7:30 AM start
Bank of America Chicago Marathon
A World Marathon Major winds through dozens of neighborhoods and cheering the route needs no bib.
Limited Run
#2Sunday, October 11, 2026, 7:30 AM start · Limited Run
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsBank of America Chicago Marathon
A World Marathon Major winds through dozens of neighborhoods and cheering the route needs no bib.
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
Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & BucktownGazeboJake · CC0 · Wikimedia CommonsSunday, October 11, 2026, 3:00–5:00 PMFREE
Chicago Latino Dance Festival at Humboldt
Eight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
FreeOne Day Only
#4Sunday, October 11, 2026, 3:00–5:00 PM · One Day Only
Humboldt (Alexander Von) Park, Humboldt Park, Logan Square, Wicker Park & BucktownGazeboJake · CC0 · Wikimedia CommonsChicago Latino Dance Festival at Humboldt
Eight companies dance free and outdoors in Humboldt Park, from Afro-Latin to folkloric styles.
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#5
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsThrough Oct 11, 2026
Operation Mincemeat: A New Musical
The Olivier-winning musical about a WWII deception plot built around a dead body.
One Weekend Only
#5Through Oct 11, 2026 · One Weekend Only
CIBC Theatre, Downtown, the Loop & West LoopOnasill - Bill Badzo - 144 Million Views from Canada · Public domain · Wikimedia CommonsOperation Mincemeat: A New Musical
The Olivier-winning musical about a WWII deception plot built around a dead body.
Add to calendar#6
Sun, Oct 11, 2026 · 7:00pm
Interpol – 2026 North American Tour
The band's North American tour hits the Salt Shed, with DIIV as special guest.
One Day Only
#6Sun, Oct 11, 2026 · 7:00pm · One Day Only
Interpol – 2026 North American Tour
The band's North American tour hits the Salt Shed, with DIIV as special guest.
Add to calendar#7
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
#7Fri, 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#8
Jonquil Park, Lincoln Park, Lakeview & WrigleyvilleWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsOctober 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pmGeneral admission from $30
Lincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#8October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln Park, Lakeview & WrigleyvilleWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsLincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
Add to calendar#9
Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia CommonsSunday, October 11, 2026, 9:30 AM–4:00 PM
27th Mile Post-Race Party
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
One Day Only
#9Sunday, October 11, 2026, 9:30 AM–4:00 PM · One Day Only
Butler Field, Grant Park, Downtown, the Loop & West LoopDaniel Schwen · CC BY-SA 4.0 · Wikimedia Commons27th Mile Post-Race Party
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
Add to calendar#10
Pullman Exhibit Hall, Pullman, Hyde Park, Bronzeville & the South SideJ. W. Taylor · public domain · Wikimedia CommonsSaturday–Sunday, October 10–11, 2026, 11 a.m.–5 p.m.$21 advance through October 8
53rd Annual Historic Pullman House Tour
The 53rd Pullman House Tour opens private landmark interiors across the historic neighborhood.
One Weekend Only
#10Saturday–Sunday, October 10–11, 2026, 11 a.m.–5 p.m. · One Weekend Only
Pullman Exhibit Hall, Pullman, Hyde Park, Bronzeville & the South SideJ. W. Taylor · public domain · Wikimedia Commons53rd Annual Historic Pullman House Tour
The 53rd Pullman House Tour opens private landmark interiors across the historic neighborhood.
Add to calendar#11
Downtown St. Charles, St. Charles, Far SuburbsAneekr at English Wikipedia · CC BY-SA 3.0 · Wikimedia CommonsFriday, October 9 – Sunday, October 11, 2026
St. Charles Scarecrow Weekend
Over 120 handmade scarecrows you vote on fill downtown, plus live music, for a fall trip.
One Weekend Only
#11Friday, October 9 – Sunday, October 11, 2026 · One Weekend Only
Downtown St. Charles, St. Charles, Far SuburbsAneekr at English Wikipedia · CC BY-SA 3.0 · Wikimedia CommonsSt. Charles Scarecrow Weekend
Over 120 handmade scarecrows you vote on fill downtown, plus live music, for a fall trip.
Add to calendar#12
Studebaker Theater, The Loop, Downtown, the Loop & West LoopAlexanderUtz · CC BY-SA 4.0 · Wikimedia CommonsSunday, October 11, 2026, 6:30 PMTicketed via the Fine Arts Bu…
Exile in Bookville Presents Hernan Diaz in Conversation with Greta Johnsen
The Pulitzer winner's follow-up to Trust, in conversation at the 1898 Studebaker.
Limited Run
#12Sunday, October 11, 2026, 6:30 PM · Limited Run
Studebaker Theater, The Loop, Downtown, the Loop & West LoopAlexanderUtz · CC BY-SA 4.0 · Wikimedia CommonsExile in Bookville Presents Hernan Diaz in Conversation with Greta Johnsen
The Pulitzer winner's follow-up to Trust, in conversation at the 1898 Studebaker.
Add to calendar#13
The Morton Arboretum, Lisle, Far SuburbsDavid Wilson · CC BY 2.0 · Wikimedia CommonsFriday–Sunday, October 9–11, 2026, 10 a.m.–5 p.m.Included with Arboretum gener…
Glass Pumpkin Patch 2026
The Morton Arboretum displays more than 8,000 glass pumpkins with live glassmaking demonstrations.
One Weekend Only
#13Friday–Sunday, October 9–11, 2026, 10 a.m.–5 p.m. · One Weekend Only
The Morton Arboretum, Lisle, Far SuburbsDavid Wilson · CC BY 2.0 · Wikimedia CommonsGlass Pumpkin Patch 2026
The Morton Arboretum displays more than 8,000 glass pumpkins with live glassmaking demonstrations.
Add to calendar#14
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsFriday–Sunday, October 9–11, 2026 · 6:30–10:30 PM nightlyAdults from $24 for nonmember…
Night of 1,000 Jack-o'-Lanterns
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
One Weekend Only
#14Friday–Sunday, October 9–11, 2026 · 6:30–10:30 PM nightly · One Weekend Only
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsNight of 1,000 Jack-o'-Lanterns
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
Add to calendar#15
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
#15Open 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#16
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
#16October 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#17
Griffin Museum of Science and Industry, Hyde Park, Bronzeville & the South SideSaturday–Sunday, October 10–11, 2026 · Start times 5–8:30 PM$40 adults
Escape the Museum: The Infinite Grid
A museum-wide escape game turns exhibits into clues across two after-hours nights.
ArtOne Weekend Only
#17Saturday–Sunday, October 10–11, 2026 · Start times 5–8:30 PM · One Weekend Only
Griffin Museum of Science and Industry, Hyde Park, Bronzeville & the South SideEscape the Museum: The Infinite Grid
A museum-wide escape game turns exhibits into clues across two after-hours nights.
Add to calendar#18
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
#18September 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#19
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsThrough Oct 11, 2026From $34 in person
Mean Girls
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Limited Run
#19Through Oct 11, 2026 · Limited Run
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsMean Girls
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Add to calendar#20
Logan Center for the Arts, Hyde Park, Bronzeville & the South SideCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsOn view July 10 – October 11, 2026
Longer Than the Sky: Art of the Obama Years
This survey gathers nearly forty works made in the Obama years, several by Chicago artists.
ArtLimited Run
#20On view July 10 – October 11, 2026 · Limited Run
Logan Center for the Arts, Hyde Park, Bronzeville & the South SideCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsLonger Than the Sky: Art of the Obama Years
This survey gathers nearly forty works made in the Obama years, several by Chicago artists.
Add to calendar#21
Donald E. Stephens Convention Center, 9301 Bryn Mawr Avenue, Evanston & Oak ParkSaturday, October 10 – Sunday, October 11, 2026; Saturday 10am–6pm, Sunday 10am–5pm
Collect-A-Con Chicago
A two-day trading-card and collectibles convention with vendors from across the hobby.
One Weekend Only
#21Saturday, October 10 – Sunday, October 11, 2026; Saturday 10am–6pm, Sunday 10am–5pm · One Weekend Only
Donald E. Stephens Convention Center, 9301 Bryn Mawr Avenue, Evanston & Oak ParkCollect-A-Con Chicago
A two-day trading-card and collectibles convention with vendors from across the hobby.
Add to calendar#22
Sun, Oct 11, 2026 · 8:00pm
Metaphor: ReFantazio Orchestra Concert
A live orchestra plays Shoji Meguro's score for the ATLUS RPG, touring after selling out in Japan.
One Day Only
#22Sun, Oct 11, 2026 · 8:00pm · One Day Only
Metaphor: ReFantazio Orchestra Concert
A live orchestra plays Shoji Meguro's score for the ATLUS RPG, touring after selling out in Japan.
Add to calendar#23
Hyatt Regency O'Hare Chicago, Rosemont, Evanston & Oak ParkFriday–Sunday, October 9–11, 2026 · Program times TBAAt door: $70 adult weekend
Windycon 52: Sanctuary Among the Stars
Chicago’s long-running sci-fi convention brings literary, gaming, art and fan programs.
One Weekend Only
#23Friday–Sunday, October 9–11, 2026 · Program times TBA · One Weekend Only
Hyatt Regency O'Hare Chicago, Rosemont, Evanston & Oak ParkWindycon 52: Sanctuary Among the Stars
Chicago’s long-running sci-fi convention brings literary, gaming, art and fan programs.
Add to calendar#24
Aragon Ballroom, 1106 W Lawrence, Andersonville, Uptown & Lincoln SquareSun, Oct 11, 2026 · 6:00pm
Taste of Chaos: Hollywood Undead & In This Moment
This touring concert plays the Aragon Ballroom's big room for one night only.
Limited Run
#24Sun, Oct 11, 2026 · 6:00pm · Limited Run
Aragon Ballroom, 1106 W Lawrence, Andersonville, Uptown & Lincoln SquareTaste of Chaos: Hollywood Undead & In This Moment
This touring concert plays the Aragon Ballroom's big room for one night only.
Add to calendar