#1
Fri, Oct 9, 2026 · 7pm; Sat, Oct 10 · 5pm and 8pmTicket required
Jerry Seinfeld Live!
Downtown, the Loop & West Loop
The stand-up legend does a live set at the Chicago Theatre, one night only.
One Weekend Only
Date night in Downtown, the Loop & West Loop Columbus Day Weekend 2026
18 picks
The 10 best date night picks in Downtown, the Loop & West Loop over Columbus Day Weekend (Oct 9–12)
- Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
- Operation Mincemeat: A New Musical — Through Oct 11 · Downtown
- Jekyll& Hyde — Oct 2–Oct 18, 2026 · Downtown
- Drunk Shakespeare: Drunk Dracula (21+ Event) — Runs through Oct 9 · Downtown
- Play On! — Chicago Shakespeare Theater — September 11–October 18; selected performances · Downtown
- Kowalski — September 15 – October 25 · Downtown
- Faust with Live Score by ten thousand lakes — Monday 7pm · Downtown
- Paul Elia at The Comedy Bar — Fri, Oct 9 7:00pm · $25 – $35 · Downtown
- Theater of the Mind — Sep 18–Oct 18, 2026 · Downtown
- Tim Shropshire at The Comedy Bar — Sun, Oct 11 6:30pm · $25 – $35 · Downtown
#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
Downtown, the Loop & West Loop
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
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West LoopOct 2, 2026–Oct 18, 2026
Jekyll& Hyde
Downtown, the Loop & West Loop
Jekyll& Hyde is listed for Chicago this weekend.
Limited Run
#3Oct 2, 2026–Oct 18, 2026 · Limited Run
Broadway Playhouse at Water Tower Place, Downtown, the Loop & West Loop#4
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopRuns through Oct 9, 2026
Drunk Shakespeare: Drunk Dracula (21+ Event)
Downtown, the Loop & West Loop
A gothic comedy remixes Dracula with an audience-facing, adults-only Shakespeare format.
Limited Run
#4Runs through Oct 9, 2026 · Limited Run
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopDrunk Shakespeare: Drunk Dracula (21+ Event)
A gothic comedy remixes Dracula with an audience-facing, adults-only Shakespeare format.
Add to calendar#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
Downtown, the Loop & West Loop
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 CommonsSeptember 15 – October 25, 2026Ticketed via Lookingglass The…
Kowalski
Downtown, the Loop & West Loop
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
Limited Run
#6September 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#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
Downtown, the Loop & West Loop
The Gene Siskel Film Center screens Faust with a live score by ten thousand lakes.
One Day Only
#7Monday 7pm · One Day Only
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
Downtown, the Loop & West Loop
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 LoopSep 18, 2026–Oct 18, 2026
Theater of the Mind
Downtown, the Loop & West Loop
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
The Comedy Bar, Downtown, the Loop & West LoopSun, Oct 11, 2026 · 6:30pm$25 – $35
Tim Shropshire at The Comedy Bar
Downtown, the Loop & West Loop
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 calendarMore this weekend
#11
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre, Downtown, the Loop & West LoopFri, Oct 9, 2026 · 7:30pm
(dark) Toilet Fire (matter(s))
Downtown, the Loop & West Loop
(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
Downtown, the Loop & West Loop
Starship Troopers has enough weekend energy to earn a spot on the board.
One Day Only
#12Saturday 2pm · One Day Only
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
Downtown, the Loop & West Loop
Destroy ALL Monsters has enough weekend energy to earn a spot on the board.
One Day Only
#13Friday 6:30pm · One Day Only
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
Gene Siskel Film Center, Downtown, the Loop & West LoopSunday 12pm
Hackers
Downtown, the Loop & West Loop
Hackers has enough weekend energy to earn a spot on the board.
One Day Only
#14Sunday 12pm · One Day Only
Gene Siskel Film Center, Downtown, the Loop & West LoopThe whole weekend, in one email.
Friday at 5pm, one email. Unsubscribe anytime.
#15
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday 6pm
How Lucky Can One Man Get
Downtown, the Loop & West Loop
How Lucky Can One Man Get has enough weekend energy to earn a spot on the board.
One Day Only
#15Friday 6pm · One Day Only
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#16
Gene Siskel Film Center, Downtown, the Loop & West LoopSaturday 7pm
The Scout
Downtown, the Loop & West Loop
The Scout has enough weekend energy to earn a spot on the board.
One Day Only
#16Saturday 7pm · One Day Only
Gene Siskel Film Center, Downtown, the Loop & West Loop#17
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
Downtown, the Loop & West Loop
Late Nite Mic w/ Vik Pandya at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#17Mon, 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#18
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
Downtown, the Loop & West Loop
Carrie Nation and the Speakeasy, the Fabulous Cowboys has enough weekend energy to earn a spot on the board.
One Day Only
#18Fri, Oct 9, 2026 · 9:00pm · One Day Only
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 calendarAbout this list
Stumblday's hand-checked ranking of the best date night in Downtown, the Loop & West Loop over Columbus Day weekend 2026 (Oct 10–12): 18 picks.
