#1
Sun, Oct 11, 2026 · 7:00pm
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 Sunday Night, Columbus Day Weekend 2026
63 picks
The 10 best things to do in Chicago on Sunday night, Oct 11
- Olivia Rodrigo – The Unraveled Tour — Sun, Oct 11 7:00pm · Pilsen
- 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
- Topdog/Underdog — Runs September 18–October 18 · Lincoln Park
- Exile in Bookville Presents Hernan Diaz in Conversation with Greta Johnsen — Sunday, October 11, 6:30 PM · The Loop
- Jekyll& Hyde — Oct 2–Oct 18, 2026 · Downtown
- Night of 1,000 Jack-o'-Lanterns — October 7–11, 14–18 and 21–25, 6:30–10:30 PM · Adults from $24 for nonmember… · Glencoe
- Mean Girls — Through Oct 11 · From $34 in person · Aurora
#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
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
#2Sunday, 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#3
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
#3October 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#4
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
#4Through 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#5
Sun, Oct 11, 2026 · 7:00pm
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
#5Sun, 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#6
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
#6Runs 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#7
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
#7Sunday, 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#8
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
#8Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#9
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
#9October 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#10
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
#10Through 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 calendarMore on Sunday night
#11
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
#11September 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#12
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
#12September 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#13
Sun, Oct 11, 2026 · 8:00pm
Metaphor: ReFantazio Orchestra Concert
Downtown, the Loop & West Loop
A live orchestra plays Shoji Meguro's score for the ATLUS RPG, touring after selling out in Japan.
One Day Only
#13Sun, 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#14
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleOct 2, 2026–Oct 18, 2026
Vladimir
Lincoln Park, Lakeview & Wrigleyville
Vladimir is listed for Chicago this weekend.
Limited Run
#14Oct 2, 2026–Oct 18, 2026 · Limited Run
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleThe whole weekend, in one email.
Friday at 5pm, one email. Unsubscribe anytime.
#15
Aragon Ballroom, 1106 W Lawrence, Andersonville, Uptown & Lincoln SquareSun, Oct 11, 2026 · 6:00pm
Taste of Chaos: Hollywood Undead & In This Moment
Andersonville, Uptown & Lincoln Square
This touring concert plays the Aragon Ballroom's big room for one night only.
One Day Only
#15Sun, Oct 11, 2026 · 6:00pm · One Day Only
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#16
Music Box Theatre, Southport Corridor, LakeviewSunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM$20 individual programs
Cinema Femme Short Film Festival 2026
Southport Corridor, Lakeview
The festival opens Sunday, then pairs a panel with two shorts programs.
One Weekend Only
#16Sunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM · One Weekend Only
Music Box Theatre, Southport Corridor, LakeviewCinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
Add to calendar#17
Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM
Music Theater Works Presents: Escape to Margaritaville
9501 Skokie Blvd, Evanston & Oak Park
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
One Weekend Only
#17Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM · One Weekend Only
Music Theater Works Presents: Escape to Margaritaville
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
Add to calendar#18
Smart Museum of Art, Hyde ParkSunday, October 11, 2026 · 4–5 PMFREE
teamLab & Allison Martino in Conversation
Smart Museum of Art, Hyde Park
A teamLab member and the exhibition curator discuss the collective’s creative practice.
FreeOne Day Only
#18Sunday, October 11, 2026 · 4–5 PM · One Day Only
Smart Museum of Art, Hyde ParkteamLab & Allison Martino in Conversation
A teamLab member and the exhibition curator discuss the collective’s creative practice.
Add to calendar#19
Green Mill Cocktail Lounge, UptownKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsSaturdays at 3pm (doors 1pm); no end date announcedFREE
The Paper Machete
Green Mill Cocktail Lounge, Uptown
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
FreeLimited Run
#19Saturdays at 3pm (doors 1pm); no end date announced · Limited Run
Green Mill Cocktail Lounge, UptownKenneth 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#20
Inside Chicago Walking Tours, Downtown, the Loop & West LoopSep 18, 2026–Oct 17, 2026
Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Downtown, the Loop & West Loop
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Limited Run
#20Sep 18, 2026–Oct 17, 2026 · Limited Run
Inside Chicago Walking Tours, Downtown, the Loop & West LoopHaunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Haunted by Our Dark Side: Chicago Ghosts, Gangsters and True Crime Tour is listed for Chicago.
Add to calendar#21
Park West, Lincoln ParkSun, Oct 11, 2026 · 7:00pm
Kanan Gill: Not This Again
Park West, Lincoln Park
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
One Day Only
#21Sun, Oct 11, 2026 · 7:00pm · One Day Only
Park West, Lincoln ParkKanan Gill: Not This Again
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
Add to calendar#22
Northlight Theatre, EvanstonSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
Northlight Theatre, Evanston
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Limited Run
#22September 9 – October 25, 2026 (extended) · Limited Run
Northlight Theatre, EvanstonThe Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendar#23
Arcada Theatre, St. Charles, Far SuburbsSaturday, October 10 and Sunday, October 11, 2026, 7:00 PMTicketed via the Arcada Theat…
W.a.s.p. – 1984 to Headless, with special guest KK's Priest
St. Charles, Far Suburbs
W.a.s.p. – 1984 to Headless, with special guest KK's Priest has enough weekend energy to earn a spot on the board.
One Weekend Only
#23Saturday, October 10 and Sunday, October 11, 2026, 7:00 PM · One Weekend Only
Arcada Theatre, St. Charles, Far SuburbsW.a.s.p. – 1984 to Headless, with special guest KK's Priest
W.a.s.p. – 1984 to Headless, with special guest KK's Priest has enough weekend energy to earn a spot on the board.
Add to calendar#24
Begyle Brewing and Dovetail Brewery, Ravenswood, Andersonville, Uptown & Lincoln SquareSaturday, October 10, 11:00 AM–9:00 PM, and Sunday, October 11, 11:00 AM–8:00 PM, 2026Free
Oktoberfestiversary
Andersonville, Uptown & Lincoln Square
Oktoberfestiversary has enough weekend energy to earn a spot on the board.
FreeOne Weekend Only
#24Saturday, October 10, 11:00 AM–9:00 PM, and Sunday, October 11, 11:00 AM–8:00 PM, 2026 · One Weekend Only
Begyle Brewing and Dovetail Brewery, Ravenswood, Andersonville, Uptown & Lincoln SquareOktoberfestiversary
Oktoberfestiversary has enough weekend energy to earn a spot on the board.
Add to calendarAbout this list
Stumblday's hand-checked ranking of the best things to do in Chicago on Sunday night of Columbus Day weekend, Oct 11: 63 picks, refreshed weekly.
