#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
Date night in Chicago on Sunday, Oct 18
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best date night in Chicago on Sunday, Oct 18: 44 picks, refreshed weekly.
44 picks · checked Sep 28
44 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.
Add to calendar#2
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
#2September 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#3
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
#3October 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.
Add to calendar#4
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
#4August 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#5
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
#5Sep 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.
Add to calendar#6
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
#6Sep 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.
Add to calendar#7
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
#7Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West Loop#8
Open Space ArtsSep 25, 2026–Oct 18, 2026$30.00
The Swallow
The Swallow is listed for Chicago this weekend.
Limited Run
#8Sep 25, 2026–Oct 18, 2026 · Limited Run
Open Space Arts#9
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
#9Sep 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.
Add to calendar#10
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
#10Sep 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.
Add to calendarMore picks for Oct 16–18, 2026
#11
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
#11Sep 20, 2026–Oct 18, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#12
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
#12Sep 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.
Add to calendar#13
Theatre Y#13Sep 24, 2026–Oct 18, 2026 · Limited Run
Theatre Y#14
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
#14Sunday, 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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#15
Gene Siskel Film Center, Downtown, the Loop & West Loop#15Sunday 5:30pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#16
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
#16October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#17
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
#17September 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#18
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
#18Sep 5 – Oct 25, 2026 · Limited Run
Black Ensemble Theater, Uptown#19
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
#19Oct 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.
Add to calendar#20
Stolp Island Theatre, Aurora, Far SuburbsOctober 7, 2026 – January 3, 2027$87 in person
Million Dollar Quartet
Million Dollar Quartet is listed for Chicago this weekend.
Limited Run
#20October 7, 2026 – January 3, 2027 · Limited Run
Stolp Island Theatre, Aurora, Far Suburbs#21
Goodman Theatre, Owen Theatre, The LoopSeptember 26 – November 1, 2026Tickets via the Goodman
Dead Girl's Quinceañera
Three friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Limited Run
#21September 26 – November 1, 2026 · Limited Run
Goodman Theatre, Owen Theatre, The LoopDead Girl's Quinceañera
Three friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Add to calendar#22
Northlight Theatre, EvanstonSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
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
Gene Siskel Film Center, Downtown, the Loop & West Loop#23Sunday 12pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#24
Downstairs Theatre At Steppenwolf Theatre – ChicagoOct 2, 2026–Oct 17, 2026$50 – $171
Topdog/Underdog – Chicago
Topdog/Underdog – Chicago is listed for Chicago this weekend.
Limited Run
#24Oct 2, 2026–Oct 17, 2026 · Limited Run
Downstairs Theatre At Steppenwolf Theatre – ChicagoTopdog/Underdog – Chicago
Topdog/Underdog – Chicago is listed for Chicago this weekend.
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