#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 the Weekend of Oct 16–18, 2026
Hand-picked every week — checked against organizers’ own pages.
Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Oct 16–18, 2026: 93 picks, refreshed weekly.
93 picks · checked Sep 28
93 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.
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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
#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.
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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
#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.
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The Annoyance TheatreSep 18, 2026–Oct 16, 2026$15
Missed Call Sketch Comedy Show
Missed Call Sketch Comedy Show is listed for Chicago this weekend.
Limited Run
#5Sep 18, 2026–Oct 16, 2026 · Limited Run
The Annoyance TheatreMissed Call Sketch Comedy Show
Missed Call Sketch Comedy Show is listed for Chicago this weekend.
Add to calendar#6
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.
Add to calendar#7
Judy’s Beat Lounge at the Second City Training CenterSep 19, 2026–Oct 17, 2026$25
Standup Throw Down: Millennials vs Gen X
Standup Throw Down: Millennials vs Gen X is listed for Chicago this weekend.
Limited Run
#7Sep 19, 2026–Oct 17, 2026 · Limited Run
Judy’s Beat Lounge at the Second City Training CenterStandup Throw Down: Millennials vs Gen X
Standup Throw Down: Millennials vs Gen X is listed for Chicago this weekend.
Add to calendar#8
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.
Add to calendar#9
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareSep 19, 2026–Oct 17, 2026
Kino, Kaffee und Kuchen
Kino, Kaffee und Kuchen is listed for Chicago this weekend.
Limited Run
#9Sep 19, 2026–Oct 17, 2026 · Limited Run
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln Square#10
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
#10Sep 18, 2026–Oct 18, 2026 · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopMore picks for Oct 16–18, 2026
#11
Annoyance Theatre & BarSep 18, 2026–Oct 17, 2026Free
Comedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre is listed for Chicago this weekend.
FreeLimited Run
#11Sep 18, 2026–Oct 17, 2026 · Limited Run
Annoyance Theatre & BarComedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre is listed for Chicago this weekend.
Add to calendar#12
Open Space ArtsSep 25, 2026–Oct 18, 2026$30.00
The Swallow
The Swallow is listed for Chicago this weekend.
Limited Run
#12Sep 25, 2026–Oct 18, 2026 · Limited Run
Open Space Arts#13
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USASep 18, 2026–Oct 16, 2026$15
Voila: The Improvised Musical
Voila: The Improvised Musical is listed for Chicago this weekend.
Limited Run
#13Sep 18, 2026–Oct 16, 2026 · Limited Run
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USAVoila: The Improvised Musical
Voila: The Improvised Musical is listed for Chicago this weekend.
Add to calendar#14
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
#14Sep 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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#15
Stars and Garters TheaterSep 18, 2026–Oct 16, 2026
Rising Stars Burlesque Revue
Rising Stars Burlesque Revue is listed for Chicago this weekend.
Limited Run
#15Sep 18, 2026–Oct 16, 2026 · Limited Run
Stars and Garters TheaterRising Stars Burlesque Revue
Rising Stars Burlesque Revue is listed for Chicago this weekend.
Add to calendar#16
de Maat Theatre at Second CitySep 19, 2026–Oct 17, 2026$20
The Improvised Movie: Summer Blockbusters
The Improvised Movie: Summer Blockbusters is listed for Chicago this weekend.
Limited Run
#16Sep 19, 2026–Oct 17, 2026 · Limited Run
de Maat Theatre at Second CityThe Improvised Movie: Summer Blockbusters
The Improvised Movie: Summer Blockbusters is listed for Chicago this weekend.
Add to calendar#17
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSep 19, 2026–Oct 17, 2026$25
Saturday Night Sketch
Saturday Night Sketch is listed for Chicago this weekend.
Limited Run
#17Sep 19, 2026–Oct 17, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#18
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
#18Sep 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 calendar#19
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
#19Sep 20, 2026–Oct 18, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#20
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
#20Sep 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#21
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSep 18, 2026–Oct 16, 2026$15
Kohl’s Cash: Tgif (That’s Good Improv Friday)
Kohl’s Cash: Tgif (That’s Good Improv Friday) is listed for Chicago this weekend.
Limited Run
#21Sep 18, 2026–Oct 16, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & WrigleyvilleKohl’s Cash: Tgif (That’s Good Improv Friday)
Kohl’s Cash: Tgif (That’s Good Improv Friday) is listed for Chicago this weekend.
Add to calendar#22
The Second City, Lincoln Park, Lakeview & WrigleyvilleSep 19, 2026–Oct 17, 2026$25
Baby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical is listed for Chicago this weekend.
Limited Run
#22Sep 19, 2026–Oct 17, 2026 · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvilleBaby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical is listed for Chicago this weekend.
Add to calendar#23
Theatre Y#23Sep 24, 2026–Oct 18, 2026 · Limited Run
Theatre Y#24
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
#24Sunday, 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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