#1
Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pm
Jerry Seinfeld Live!
The stand-up legend does a live set at the Chicago Theatre, one night only.
One Weekend Only
Date night in West Loop, Chicago the Weekend of Oct 9–12, 2026
Stumblday's hand-checked ranking of the best date night in West Loop, Chicago, Downtown, the Loop & West Loop the weekend of Oct 9–12, 2026: 20 picks.
20 picks · checked Sep 21
20 picks
#1Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pm · One Weekend Only
Jerry Seinfeld Live!
The stand-up legend does a live set at the Chicago Theatre, one night only.
Add to calendar#2
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
The Olivier-winning musical about a WWII deception plot built around a dead body.
One Weekend Only
#2Through 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#3
Lyric Opera House, Downtown, the Loop & West LoopZesmeralda · CC BY-SA 2.0 · Wikimedia CommonsSat, Oct 10, 2026 · 7:30pm
Don Giovanni
Lyric opens its 2026/27 season with the tale of a charismatic lord's spectacular downfall.
One Day Only
#3Sat, Oct 10, 2026 · 7:30pm · One Day Only
Lyric Opera House, Downtown, the Loop & West LoopZesmeralda · CC BY-SA 2.0 · Wikimedia CommonsDon Giovanni
Lyric opens its 2026/27 season with the tale of a charismatic lord's spectacular downfall.
Add to calendar#4
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsFriday 7 PM; Saturday 2 & 7:30 PM; Sunday 1 & 6:30 PM
Jekyll & Hyde
The gothic musical plays five weekend performances at Broadway Playhouse.
Limited Run
#4Friday 7 PM; Saturday 2 & 7:30 PM; Sunday 1 & 6:30 PM · Limited Run
Broadway Playhouse at Water Tower Place, 175 E. Chestnut St, Downtown, the Loop & West Loopw_lemay · CC BY-SA 2.0 · Wikimedia CommonsJekyll & Hyde
The gothic musical plays five weekend performances at Broadway Playhouse.
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#5
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
#5September 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#6
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSaturday, October 10, 2026 · 2 PM audio-described performanceTicketed via Lookingglass The…
Kowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
One Day Only
#6Saturday, October 10, 2026 · 2 PM audio-described performance · One Day Only
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#7
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsMonday 7pm
Faust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Limited Run
#7Monday 7pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsFaust with Live Score by ten thousand lakes
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
Add to calendar#8
The Comedy Bar, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 7:00pm$25 – $35
Paul Elia at The Comedy Bar
Paul Elia at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Weekend Only
#8Fri, Oct 9, 2026 · 7:00pm · One Weekend Only
The Comedy Bar, Downtown, the Loop & West LoopPaul Elia at The Comedy Bar
Paul Elia at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#9
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopExtended through November 15, 2026; 75-minute timed performances
Theater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Limited Run
#9Extended through November 15, 2026; 75-minute timed performances · Limited Run
Reid Murdoch Building – 333 N LaSalle, Downtown, the Loop & West LoopTheater of the Mind
Theater of the Mind has enough weekend energy to earn a spot on the board.
Add to calendar#10
The Comedy Bar, Downtown, the Loop & West LoopSun, Oct 11, 2026 · 6:30pm$25 – $35
Tim Shropshire at The Comedy Bar
Tim Shropshire at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#10Sun, Oct 11, 2026 · 6:30pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopTim Shropshire at The Comedy Bar
Tim Shropshire at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#11
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 7:30pm
(dark) Toilet Fire (matter(s))
(dark) Toilet Fire (matter(s)) has enough weekend energy to earn a spot on the board.
One Weekend Only
#11Fri, Oct 9, 2026 · 7:30pm · One Weekend Only
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre, Downtown, the Loop & West Loop(dark) Toilet Fire (matter(s))
(dark) Toilet Fire (matter(s)) has enough weekend energy to earn a spot on the board.
Add to calendar#12
Gene Siskel Film Center, Downtown, the Loop & West LoopSaturday 2pm
Starship Troopers
Starship Troopers has enough weekend energy to earn a spot on the board.
Limited Run
#12Saturday 2pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopStarship Troopers
Starship Troopers has enough weekend energy to earn a spot on the board.
Add to calendar#13
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday 6:30pm
Destroy ALL Monsters
Destroy ALL Monsters has enough weekend energy to earn a spot on the board.
Limited Run
#13Friday 6:30pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopDestroy ALL Monsters
Destroy ALL Monsters has enough weekend energy to earn a spot on the board.
Add to calendar#14
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 7:00pm
Drunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) has enough weekend energy to earn a spot on the board.
Limited Run
#14Fri, Oct 9, 2026 · 7:00pm · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
Drunk Shakespeare: Drunk Dracula (21+ Event) has enough weekend energy to earn a spot on the board.
Add to calendar#15
Gene Siskel Film Center, Downtown, the Loop & West Loop#15Sunday 12pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#16
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday 6pm
How Lucky Can One Man Get
How Lucky Can One Man Get has enough weekend energy to earn a spot on the board.
Limited Run
#16Friday 6pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West LoopHow Lucky Can One Man Get
How Lucky Can One Man Get has enough weekend energy to earn a spot on the board.
Add to calendar#17
Gene Siskel Film Center, Downtown, the Loop & West Loop#17Saturday 7pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#18
The Comedy Bar, Downtown, the Loop & West LoopMon, Oct 12, 2026 · 7:00pm$25 – $30
Late Nite Mic w/ Vik Pandya at The Comedy Bar
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#18Mon, Oct 12, 2026 · 7:00pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopLate Nite Mic w/ Vik Pandya at The Comedy Bar
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#19
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 9:00pm
Carrie Nation and the Speakeasy, the Fabulous Cowboys
Carrie Nation and the Speakeasy, the Fabulous Cowboys has enough weekend energy to earn a spot on the board.
Limited Run
#19Fri, Oct 9, 2026 · 9:00pm · Limited Run
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West LoopCarrie Nation and the Speakeasy, the Fabulous Cowboys
Carrie Nation and the Speakeasy, the Fabulous Cowboys has enough weekend energy to earn a spot on the board.
Add to calendar#20
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopSeptember 26 – November 1, 2026Tickets via the Goodman
Dead Girl's Quinceañera
Dead Girl's Quinceañera has enough weekend energy to earn a spot on the board.
Limited Run
#20September 26 – November 1, 2026 · Limited Run
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopDead Girl's Quinceañera
Dead Girl's Quinceañera has enough weekend energy to earn a spot on the board.
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