#1
Multiple LocationsOct 16, 2026âOct 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 Saturday, Oct 17
Hand-picked every week â checked against organizersâ own pages.
Stumblday's hand-checked ranking of the best date night in Chicago on Saturday, Oct 17: 65 picks, refreshed weekly.
65 picks · checked Sep 28
65 picks
The 10 picks
Multiple Locations#1Oct 16, 2026âOct 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 11âOctober 18, 2026; selected performances
Play On! â Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Limited Run
#2September 11âOctober 18, 2026; selected performances · Limited Run
The Yard at Chicago Shakespeare Theater, Navy Pier, Downtown, the Loop & West LoopPlay On! â Chicago Shakespeare Theater
A new play runs select dates at Chicago Shakespeare's Navy Pier stage.
Add to calendar#3
Music Box Theatre, LakeviewOctober 1â31, 2026; horror screenings most nights, plus a 24-hour marathon on October 24Most screenings $13 ($10 MusiâŠ
Music Box of Horrors: The Final Chapter
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Limited Run
#3October 1â31, 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 19âOctober 18, 2026Tickets via Drury Lane box ofâŠ
The Buddy Holly Story
Buddy Hollyâs songs drive this biographical musical at Drury Lane Theatre.
Limited Run
#4August 19âOctober 18, 2026 · Limited Run
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsThe Buddy Holly Story
Buddy Hollyâs songs drive this biographical musical at Drury Lane Theatre.
Add to calendar#5
Redtwist TheatreSep 17, 2026âOct 18, 2026$50
Redtwist Theatre Presents The First Show of Its 22nd Season, âPrayer Circleâ
Redtwist Theatre Presents The First Show of Its 22nd Season, âPrayer Circleâ is listed for.
Limited Run
#5Sep 17, 2026âOct 18, 2026 · Limited Run
Redtwist TheatreRedtwist Theatre Presents The First Show of Its 22nd Season, âPrayer Circleâ
Redtwist Theatre Presents The First Show of Its 22nd Season, âPrayer Circleâ is listed for.
Add to calendar#6
Judyâs Beat Lounge at the Second City Training CenterSep 19, 2026âOct 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
#6Sep 19, 2026âOct 17, 2026 · Limited Run
Judyâs 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#7
Greenhouse Theater CenterSep 26, 2026âOct 18, 2026
If You Give a Mouse a Cookie
If You Give a Mouse a Cookie is listed for Chicago this weekend.
Limited Run
#7Sep 26, 2026âOct 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#8
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln SquareSep 19, 2026âOct 17, 2026
Kino, Kaffee und Kuchen
Kino, Kaffee und Kuchen is listed for Chicago this weekend.
Limited Run
#8Sep 19, 2026âOct 17, 2026 · Limited Run
DANK Haus German American Cultural Center, Andersonville, Uptown & Lincoln Square#9
Reid Murdoch Building â 333 N LaSalle, Downtown, the Loop & West LoopSep 18, 2026âOct 18, 2026
Theater of the Mind
Theater of the Mind is listed for Chicago this weekend.
Limited Run
#9Sep 18, 2026âOct 18, 2026 · Limited Run
Reid Murdoch Building â 333 N LaSalle, Downtown, the Loop & West Loop#10
Annoyance Theatre & BarSep 18, 2026âOct 17, 2026Free
Comedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre is listed for Chicago this weekend.
FreeLimited Run
#10Sep 18, 2026âOct 17, 2026 · Limited Run
Annoyance Theatre & BarComedy Hour at Annoyance Theatre
Comedy Hour at Annoyance Theatre is listed for Chicago this weekend.
Add to calendarMore picks for Oct 16â18, 2026
#11
Open Space ArtsSep 25, 2026âOct 18, 2026$30.00
The Swallow
The Swallow is listed for Chicago this weekend.
Limited Run
#11Sep 25, 2026âOct 18, 2026 · Limited Run
Open Space Arts#12
The iO Theater, 1501 N Kingsbury St, Chicago, IL 60642, USASep 18, 2026âOct 16, 2026$15
Voila: The Improvised Musical
Voila: The Improvised Musical is listed for Chicago this weekend.
Limited Run
#12Sep 18, 2026âOct 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#13
The Den Theatre, Logan Square, Wicker Park & BucktownSep 18, 2026âOct 18, 2026$12 â $40
Refracted Theatre Company Presents âIâm Gonna Marry You Tobey Maguireâ
Refracted Theatre Company Presents âIâm Gonna Marry You Tobey Maguireâ is listed for Chicago.
Limited Run
#13Sep 18, 2026âOct 18, 2026 · Limited Run
The Den Theatre, Logan Square, Wicker Park & BucktownRefracted Theatre Company Presents âIâm Gonna Marry You Tobey Maguireâ
Refracted Theatre Company Presents âIâm Gonna Marry You Tobey Maguireâ is listed for Chicago.
Add to calendar#14
Stars and Garters TheaterSep 18, 2026âOct 16, 2026
Rising Stars Burlesque Revue
Rising Stars Burlesque Revue is listed for Chicago this weekend.
Limited Run
#14Sep 18, 2026âOct 16, 2026 · Limited Run
Stars and Garters TheaterRising Stars Burlesque Revue
Rising Stars Burlesque Revue is listed for Chicago this weekend.
Add to calendarPlanning ahead for Oct 16â18, 2026?
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#15
de Maat Theatre at Second CitySep 19, 2026âOct 17, 2026$20
The Improvised Movie: Summer Blockbusters
The Improvised Movie: Summer Blockbusters is listed for Chicago this weekend.
Limited Run
#15Sep 19, 2026âOct 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#16
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSep 19, 2026âOct 17, 2026$25
Saturday Night Sketch
Saturday Night Sketch is listed for Chicago this weekend.
Limited Run
#16Sep 19, 2026âOct 17, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#17
Facility TheatreSep 20, 2026âOct 18, 2026$25
The 37th Annual Rhinoceros Theater Festival Returns September 20 â October 26 at Four Chicago Venues
The 37th Annual Rhinoceros Theater Festival Returns September 20 â October 26 at Four Chicago.
Limited Run
#17Sep 20, 2026âOct 18, 2026 · Limited Run
Facility TheatreThe 37th Annual Rhinoceros Theater Festival Returns September 20 â October 26 at Four Chicago Venues
The 37th Annual Rhinoceros Theater Festival Returns September 20 â October 26 at Four Chicago.
Add to calendar#18
iO Theater, Lincoln Park, Lakeview & WrigleyvilleSep 20, 2026âOct 18, 2026$15
Marquee: Musical Improv
Marquee: Musical Improv is listed for Chicago this weekend.
Limited Run
#18Sep 20, 2026âOct 18, 2026 · Limited Run
iO Theater, Lincoln Park, Lakeview & Wrigleyville#19
Marriott TheatreSep 18, 2026âOct 18, 2026$80 â $100
Marriott Theatre Presents Come From Away
Marriott Theatre Presents Come From Away is listed for Chicago this weekend.
Limited Run
#19Sep 18, 2026âOct 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#20
The Second City, Lincoln Park, Lakeview & WrigleyvilleSep 19, 2026âOct 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
#20Sep 19, 2026âOct 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#21
Theatre YSep 24, 2026âOct 18, 2026
I am the Wind
I am the Wind is listed for Chicago this weekend.
Limited Run
#21Sep 24, 2026âOct 18, 2026 · Limited Run
Theatre Y#22
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 â November 8, 2026Tickets via Raven Theatre
A Strange Loop
A Strange Loop is listed for Chicago this weekend.
Limited Run
#22October 8 â November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#23
Wintrust ArenaSaturday, October 17, 2026, 8:00 PMâ11:00 PM
Sweetest Day Comedy Jam
Sweetest Day Comedy Jam is listed for Chicago this weekend.
One Day Only
#23Saturday, October 17, 2026, 8:00 PMâ11:00 PM · One Day Only
Wintrust Arena#24
Studio5 Performing Arts CenterFriday · Oct 16, 2026âOct 17, 2026
All at Once â The Seldoms with Timothy Daisy
All at Once â The Seldoms with Timothy Daisy is listed for Chicago this weekend.
One Weekend Only
#24Friday · Oct 16, 2026âOct 17, 2026 · One Weekend Only
Studio5 Performing Arts CenterAll at Once â The Seldoms with Timothy Daisy
All at Once â The Seldoms with Timothy Daisy is listed for Chicago this weekend.
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