#1
Sun, Oct 11, 2026 · 7:00pmPaid ticket required
Olivia Rodrigo – The Unraveled Tour
Pilsen, West Town & the West Side
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, Columbus Day Weekend 2026
164 picks
The 10 best things to do in Chicago on Sunday, Oct 11
- Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
- Bank of America Chicago Marathon — Sunday, October 11, 7:30 AM start · Downtown
- Fall Fest at Lincoln Park Zoo — Sep 25–Oct 18, 2026 · Free · Lincoln Park
- Chicago Latino Dance Festival at Humboldt — Sunday, October 11, 3:00–5:00 PM · Free · Logan Square
- Lincoln Park Wine Fest — October 9–11; Friday 5–10pm · General admission from $30 · Lincoln Park
- Operation Mincemeat: A New Musical — Through Oct 11 · Downtown
- Interpol – 2026 North American Tour — Sun, Oct 11 7:00pm · Logan Square
- Don Giovanni — Oct 10–Oct 18, 2026 · Lyric Opera House
- Topdog/Underdog — Runs September 18–October 18 · Lincoln Park
- 27th Mile Post-Race Party — Sunday, October 11, 9:30 AM–4:00 PM · Downtown
#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
Downtown, the Loop & West Loop
The Chicago Marathon sends runners through the city before a Grant Park finish.
One Day Only
#2Sunday, October 11, 2026, 7:30 AM start · One Day Only
Grant Park, Downtown, the Loop & West LoopRaymondbritt · CC BY-SA 3.0 · Wikimedia CommonsBank of America Chicago Marathon
The Chicago Marathon sends runners through the city before a Grant Park finish.
Add to calendar#3
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleSep 25, 2026–Oct 18, 2026Free
Fall Fest at Lincoln Park Zoo
Lincoln Park, Lakeview & Wrigleyville
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
FreeLimited Run
#3Sep 25, 2026–Oct 18, 2026 · Limited Run
Lincoln Park Zoo, Lincoln Park, Lakeview & WrigleyvilleFall Fest at Lincoln Park Zoo
Fall Fest at Lincoln Park Zoo is listed for Chicago this weekend.
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
Logan Square, Wicker Park & Bucktown
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.
Add to calendar#5
Jonquil Park, Lincoln ParkWarren 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
Jonquil Park, Lincoln Park
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#5October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln ParkWarren 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#6
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
Downtown, the Loop & West Loop
The Olivier-winning musical about a WWII deception plot built around a dead body.
One Weekend Only
#6Through 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#7
Sun, Oct 11, 2026 · 7:00pmTicket required
Interpol – 2026 North American Tour
Logan Square, Wicker Park & Bucktown
The band's North American tour hits the Salt Shed, with DIIV as special guest.
One Day Only
#7Sun, 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#8
Lyric Opera HouseOct 10, 2026–Oct 18, 2026
Don Giovanni
Lyric Opera House
Don Giovanni is listed for Chicago this weekend.
Limited Run
#8Oct 10, 2026–Oct 18, 2026 · Limited Run
Lyric Opera House#9
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleRuns September 18–October 18, 2026; weekend performances.
Topdog/Underdog
Lincoln Park, Lakeview & Wrigleyville
Topdog/Underdog brings its two-brother drama to Steppenwolf’s Downstairs Theater.
Limited Run
#9Runs September 18–October 18, 2026; weekend performances. · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog brings its two-brother drama to Steppenwolf’s Downstairs Theater.
Add to calendar#10
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
Downtown, the Loop & West Loop
The part of marathon Sunday in Grant Park that needs no bib, to 4pm.
One Day Only
#10Sunday, 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 calendarMore on Sunday
#11
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
Hyde Park, Bronzeville & the South Side
The 53rd Pullman House Tour opens private landmark interiors across the historic neighborhood.
One Weekend Only
#11Saturday–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#12
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
St. Charles, Far Suburbs
Scarecrow Weekend fills downtown St. Charles with displays and fall activities.
One Weekend Only
#12Friday, 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
Scarecrow Weekend fills downtown St. Charles with displays and fall activities.
Add to calendar#13
Studebaker Theater, The 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
Studebaker Theater, The Loop
The Pulitzer winner's follow-up to Trust, in conversation at the 1898 Studebaker.
Limited Run
#13Sunday, October 11, 2026, 6:30 PM · Limited Run
Studebaker Theater, The 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#14
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
Lisle, Far Suburbs
The Morton Arboretum displays more than 8,000 glass pumpkins with live glassmaking demonstrations.
One Weekend Only
#14Friday–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.
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#15
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West LoopOct 2, 2026–Oct 18, 2026
Jekyll& Hyde
Downtown, the Loop & West Loop
Jekyll& Hyde is listed for Chicago this weekend.
Limited Run
#15Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#16
Chicago Botanic Garden, Glencoe, Far Suburbscultivar413 · CC BY 2.0 · Wikimedia CommonsOctober 7–11, 14–18 and 21–25, 2026, 6:30–10:30 PMAdults from $24 for nonmember…
Night of 1,000 Jack-o'-Lanterns
Glencoe, Far Suburbs
Seventy-five giant pumpkins, live carving and performers light a three-night garden walk.
One Weekend Only
#16October 7–11, 14–18 and 21–25, 2026, 6:30–10:30 PM · 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#17
F1 Arcade, River North, Downtown, the Loop & West LoopOpen this weekend — recently opened
F1 Arcade
Downtown, the Loop & West Loop
F1 Arcade is listed for Chicago this weekend.
Limited Run
#17Open this weekend — recently opened · Limited Run
F1 Arcade, River North, Downtown, the Loop & West Loop#18
Venues across Chicago, Citywide, Downtown, the Loop & West LoopMatt Reeves / Darkroom Demons · CC0 · Wikimedia CommonsOctober 8–18, 2026; events at venues across the city
Chicago Fashion Week
Downtown, the Loop & West Loop
The citywide fashion calendar spans markets, runway shows and store events.
Limited Run
#18October 8–18, 2026; events at venues across the city · 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#19
Griffin Museum of Science and IndustryOct 10, 2026–Oct 16, 2026$40.00
Escape the Museum at Griffin Museum of Science and Industry
Griffin Museum of Science and Industry
Escape the Museum at Griffin Museum of Science and Industry is listed for Chicago this weekend.
ArtOne Weekend Only
#19Oct 10, 2026–Oct 16, 2026 · One Weekend Only
Griffin Museum of Science and IndustryEscape the Museum at Griffin Museum of Science and Industry
Escape the Museum at Griffin Museum of Science and Industry is listed for Chicago this weekend.
Add to calendar#20
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsThrough Oct 11, 2026From $34 in person
Mean Girls
Aurora, Far Suburbs
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Limited Run
#20Through 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#21
Logan Center for the Arts, Hyde ParkCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsOn view July 10 – October 11, 2026
Longer Than the Sky: Art of the Obama Years
Logan Center for the Arts, Hyde Park
A curator-led 11 a.m. walkthrough adds a timed hook to this Obama-era art survey.
ArtLimited Run
#21On view July 10 – October 11, 2026 · Limited Run
Logan Center for the Arts, Hyde ParkCharter6281 · CC BY-SA 4.0 · Wikimedia CommonsLonger Than the Sky: Art of the Obama Years
A curator-led 11 a.m. walkthrough adds a timed hook to this Obama-era art survey.
Add to calendar#22
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopSeptember 11–October 18, 2026; selected performances
Play On! — Chicago Shakespeare Theater
Downtown, the Loop & West Loop
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#22September 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#23
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Downtown, the Loop & West Loop
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#23September 15 – October 25, 2026 · Limited Run
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsKowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Add to calendar#24
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
9301 Bryn Mawr Avenue, Evanston & Oak Park
A two-day trading-card and collectibles convention with vendors from across the hobby.
One Weekend Only
#24Saturday, 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 calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Chicago on Sunday of Columbus Day weekend, Oct 11: 164 picks, refreshed weekly.
