#1
Multiple LocationsOct 16, 2026–Oct 18, 2026
62nd Chicago International Film Festival
62nd Chicago International Film Festival is listed for Chicago this weekend.
One Weekend Only
Things to Do in Chicago Sunday Night, Oct 18
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best things to do in Chicago on Sunday night, Oct 18: 51 picks, refreshed weekly.
51 picks · checked Sep 28
51 picks
The 10 picks
Multiple Locations#1Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Multiple Locations62nd Chicago International Film Festival
62nd Chicago International Film Festival is listed for Chicago this weekend.
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Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West LoopThursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026Free and open to the public
ART on THE Mart
ART on THE Mart is listed for Chicago this weekend.
FreeArt
#2Thursdays through Sundays, 7:30–8:00 PM, through Nov 15, 2026 · Limited Run
Chicago Riverwalk (Wells St. to Franklin St.), River North, Downtown, the Loop & West Loop#3
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
#3September 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.
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Music Box Theatre, LakeviewOctober 1–31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24Most screenings $13 ($10 Musi…
Music Box of Horrors: The Final Chapter
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Limited Run
#4October 1–31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24 · Limited Run
Music Box Theatre, LakeviewMusic Box of Horrors: The Final Chapter
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
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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
#5August 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.
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Redtwist TheatreSep 17, 2026–Oct 18, 2026$50
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” is listed for.
Limited Run
#6Sep 17, 2026–Oct 18, 2026 · Limited Run
Redtwist TheatreRedtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle”
Redtwist Theatre Presents The First Show of Its 22nd Season, “Prayer Circle” is listed for.
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House of Blues Chicago, River North, Downtown, the Loop & West LoopSep 13, 2026–Oct 18, 2026
World Famous Gospel Brunch at House of Blues (CHI)
World Famous Gospel Brunch at House of Blues (CHI) is listed for Chicago this weekend.
Limited Run
#7Sep 13, 2026–Oct 18, 2026 · Limited Run
House of Blues Chicago, River North, Downtown, the Loop & West LoopWorld Famous Gospel Brunch at House of Blues (CHI)
World Famous Gospel Brunch at House of Blues (CHI) is listed for Chicago this weekend.
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Greenhouse Theater CenterSep 26, 2026–Oct 18, 2026
If You Give a Mouse a Cookie
If You Give a Mouse a Cookie is listed for Chicago this weekend.
Limited Run
#8Sep 26, 2026–Oct 18, 2026 · Limited Run
Greenhouse Theater CenterIf You Give a Mouse a Cookie
If You Give a Mouse a Cookie is listed for Chicago this weekend.
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Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopSep 18, 2026–Oct 18, 2026
Theater of the Mind
Theater of the Mind is listed for Chicago this weekend.
Limited Run
#9Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#10
Open Space ArtsSep 25, 2026–Oct 18, 2026$30.00
The Swallow
The Swallow is listed for Chicago this weekend.
Limited Run
#10Sep 25, 2026–Oct 18, 2026 · Limited Run
Open Space ArtsMore picks for Oct 16–18, 2026
#11
Chicago’s First Lady CruisesSep 18, 2026–Oct 18, 2026$50
Chicago By Night River & Lake
Chicago By Night River & Lake is listed for Chicago this weekend.
Limited Run
#11Sep 18, 2026–Oct 18, 2026 · Limited Run
Chicago’s First Lady CruisesChicago By Night River & Lake
Chicago By Night River & Lake is listed for Chicago this weekend.
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The Den Theatre, Logan Square, Wicker Park & BucktownSep 18, 2026–Oct 18, 2026$12 – $40
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire”
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” is listed for Chicago.
Limited Run
#12Sep 18, 2026–Oct 18, 2026 · Limited Run
The Den Theatre, Logan Square, Wicker Park & BucktownRefracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire”
Refracted Theatre Company Presents “I’m Gonna Marry You Tobey Maguire” is listed for Chicago.
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Facility TheatreSep 20, 2026–Oct 18, 2026$25
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago.
Limited Run
#13Sep 20, 2026–Oct 18, 2026 · Limited Run
Facility TheatreThe 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago Venues
The 37th Annual Rhinoceros Theater Festival Returns September 20 – October 26 at Four Chicago.
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iO Theater, Lincoln Park, Lakeview & WrigleyvilleSep 20, 2026–Oct 18, 2026$15
Marquee: Musical Improv
Marquee: Musical Improv is listed for Chicago this weekend.
Limited Run
#14Sep 20, 2026–Oct 18, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & WrigleyvillePlanning ahead for Oct 16–18, 2026?
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#15
Marriott TheatreSep 18, 2026–Oct 18, 2026$80 – $100
Marriott Theatre Presents Come From Away
Marriott Theatre Presents Come From Away is listed for Chicago this weekend.
Limited Run
#15Sep 18, 2026–Oct 18, 2026 · Limited Run
Marriott TheatreMarriott Theatre Presents Come From Away
Marriott Theatre Presents Come From Away is listed for Chicago this weekend.
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Theatre Y#16Sep 24, 2026–Oct 18, 2026 · Limited Run
Theatre Y#17
Evanston Art CenterSunday, October 18, 2026, 3:00 PM–5:00 PMFree
Fashion Film Festival Chicago
Fashion Film Festival Chicago is listed for Chicago this weekend.
FreeOne Day Only
#17Sunday, October 18, 2026, 3:00 PM–5:00 PM · One Day Only
Evanston Art CenterFashion Film Festival Chicago
Fashion Film Festival Chicago is listed for Chicago this weekend.
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Gene Siskel Film Center, Downtown, the Loop & West Loop#18Sunday 5:30pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#19
Obama Presidential CenterSunday, October 18, 2026, 5:00 PM–7:00 PM$25.00
Lessons in Ethical Leadership: Speaking Stones of Emperor Ashoka (268 BCE)
Lessons in Ethical Leadership: Speaking Stones of Emperor Ashoka (268 BCE) is listed for Chicago.
One Day Only
#19Sunday, October 18, 2026, 5:00 PM–7:00 PM · One Day Only
Obama Presidential CenterLessons in Ethical Leadership: Speaking Stones of Emperor Ashoka (268 BCE)
Lessons in Ethical Leadership: Speaking Stones of Emperor Ashoka (268 BCE) is listed for Chicago.
Add to calendar#20
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 – November 8, 2026Tickets via Raven Theatre
A Strange Loop
A Strange Loop is listed for Chicago this weekend.
Limited Run
#20October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#21
Schaumburg, Far SuburbsTony Webster from Minneapolis, Minnesota, United States · CC BY-SA 2.0 · Wikimedia CommonsOct 14–17, 2026 · Convention hall Thu noon–11pm, Fri 10am–midnight, Sat 10am–1amSingle day $55 Thu or Fri
Pinball Expo 2026
The 42nd Pinball Expo fills a Schaumburg convention hall with hundreds of machines set to free play, plus tournaments and factory tours.
One Weekend Only
#21Oct 14–17, 2026 · Convention hall Thu noon–11pm, Fri 10am–midnight, Sat 10am–1am · One Weekend Only
Schaumburg, Far SuburbsTony Webster from Minneapolis, Minnesota, United States · CC BY-SA 2.0 · Wikimedia CommonsPinball Expo 2026
The 42nd Pinball Expo fills a Schaumburg convention hall with hundreds of machines set to free play, plus tournaments and factory tours.
Add to calendar#22
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
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#22September 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#23
Black Ensemble Theater, UptownSep 5 – Oct 25, 2026Ticketed via Black Ensemble T…
You Can't Fake the Funk
You Can't Fake the Funk is listed for Chicago this weekend.
Limited Run
#23Sep 5 – Oct 25, 2026 · Limited Run
Black Ensemble Theater, Uptown#24
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleOct 16, 2026–Oct 18, 2026$34 – $55
Remy Bumppo Theatre Company Presents “Mud Row”
Remy Bumppo Theatre Company Presents “Mud Row” is listed for Chicago this weekend.
One Weekend Only
#24Oct 16, 2026–Oct 18, 2026 · One Weekend Only
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleRemy Bumppo Theatre Company Presents “Mud Row”
Remy Bumppo Theatre Company Presents “Mud Row” is listed for Chicago this weekend.
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