#1
Harris Theater Rooftop, Downtown, the Loop & West LoopThrough Sep 27, 2026
Chicago Gourmet 2026
Chicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
One Weekend OnlyPopular
Date night in Downtown, the Loop & West Loop the Weekend of Sep 25–27, 2026
Stumblday's hand-checked ranking of the best date night in Downtown, the Loop & West Loop the weekend of Sep 25–27, 2026: 27 picks, refreshed weekly.
27 picks · checked Sep 21
27 picks
Harris Theater Rooftop, Downtown, the Loop & West Loop#1Through Sep 27, 2026 · One Weekend Only
Harris Theater Rooftop, Downtown, the Loop & West LoopChicago Gourmet 2026
Chicago Gourmet pairs its chef-led festival with a dance-inspired theme, including events at the Harris Theater Rooftop.
Add to calendar#2
Arie Crown Theater, Downtown, the Loop & West LoopFri, Sep 25, 2026 · 8:00pm
Martin Lawrence – Y’all Still Know What It Is! Tour
Legendary comedian and actor Martin Lawrence plays one night live at Arie Crown Theater.
One Day Only
#2Fri, Sep 25, 2026 · 8:00pm · One Day Only
Arie Crown Theater, Downtown, the Loop & West LoopMartin Lawrence – Y’all Still Know What It Is! Tour
Legendary comedian and actor Martin Lawrence plays one night live at Arie Crown Theater.
Add to calendar#3
Lyric Opera House, Loop, Downtown, the Loop & West LoopSeptember 17–27, 2026; selected performances
Liliom — The Joffrey Ballet
The Joffrey Ballet brings Molnár's Liliom to the Lyric stage for select September performances.
Limited Run
#3September 17–27, 2026; selected performances · Limited Run
Lyric Opera House, Loop, Downtown, the Loop & West LoopLiliom — The Joffrey Ballet
The Joffrey Ballet brings Molnár's Liliom to the Lyric stage for select September performances.
Add to calendar#4
Auditorium Theatre, Downtown, the Loop & West LoopCervin Robinson, photographer. · Public domain · Wikimedia CommonsSat, Sep 26, 2026 · 7:30pm
Top Gun: Maverick In Concert
The Chicago Philharmonic plays the score live as Top Gun: Maverick fills the Auditorium screen.
One Day Only
#4Sat, Sep 26, 2026 · 7:30pm · One Day Only
Auditorium Theatre, Downtown, the Loop & West LoopCervin Robinson, photographer. · Public domain · Wikimedia CommonsTop Gun: Maverick In Concert
The Chicago Philharmonic plays the score live as Top Gun: Maverick fills the Auditorium screen.
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#5
Sat, Sep 26, 2026 · 7:00pm
Bassem Youssef – The Belly of the Beast Tour
Bassem Youssef brings his comedy tour to The Chicago Theatre for one night only.
One Day Only
#5Sat, Sep 26, 2026 · 7:00pm · One Day Only
Bassem Youssef – The Belly of the Beast Tour
Bassem Youssef brings his comedy tour to The Chicago Theatre for one night only.
Add to calendar#6
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThrough Oct 4, 2026
The Attic
The 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
Limited Run
#6Through Oct 4, 2026 · Limited Run
Goodman Albert Theatre, Downtown, the Loop & West LoopMichel Curi · CC BY 2.0 · Wikimedia CommonsThe Attic
The 7 Fingers turn a former trapezist's memoir into daring aerial theater, running into October.
Add to calendar#7
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
#7September 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#8
Fri, Sep 25, 7pm; Sat, Sep 26, 2pm & 7:30pm; Sun, Sep 27, 1pm & 6:30pm
Kokandy Productions Jekyll & Hyde (Chicago)
Kokandy Productions stages the Jekyll & Hyde musical at the Broadway Playhouse at Water Tower Place.
One Weekend Only
#8Fri, Sep 25, 7pm; Sat, Sep 26, 2pm & 7:30pm; Sun, Sep 27, 1pm & 6:30pm · One Weekend Only
Kokandy Productions Jekyll & Hyde (Chicago)
Kokandy Productions stages the Jekyll & Hyde musical at the Broadway Playhouse at Water Tower Place.
Add to calendar#9
Gene Siskel Film Center, the Loop, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia CommonsSunday 7pmPasses and individual tickets…
33rd Chicago Underground Film Festival Closing Night: A Stranger Has No Eyes
The Underground Film Festival closes out with A Stranger HAS NO Eyes at Siskel.
Limited Run
#9Sunday 7pm · Limited Run
Gene Siskel Film Center, the Loop, Downtown, the Loop & West LoopMrschimpf · CC BY-SA 4.0 · Wikimedia Commons33rd Chicago Underground Film Festival Closing Night: A Stranger Has No Eyes
The Underground Film Festival closes out with A Stranger HAS NO Eyes at Siskel.
Add to calendar#10
The Chicago Theatre, Downtown, the Loop & West LoopFri, Sep 25, 2026 · 7:30pm
Laura Ramoso – The Calm Down Tour
Laura Ramoso brings The Calm Down Tour to The Chicago Theatre.
One Day Only
#10Fri, Sep 25, 2026 · 7:30pm · One Day Only
The Chicago Theatre, Downtown, the Loop & West LoopLaura Ramoso – The Calm Down Tour
Laura Ramoso brings The Calm Down Tour to The Chicago Theatre.
Add to calendar#11
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West 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
#11September 26 – November 1, 2026 · Limited Run
Goodman Theatre, Owen Theatre, The Loop, Downtown, the Loop & West LoopDead Girl's Quinceañera
Three friends investigate a classmate’s quinceañera disappearance in this comic thriller.
Add to calendar#12
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopSaturday, September 26, 2026, 2–5 p.m. or 7–10 p.m.$255+ taxes & fees
Chicago Gourmet: Grand Cru
Acclaimed chefs, winemakers and mixologists pair luxury bites and pours in two rooftop sessions.
One Day Only
#12Saturday, September 26, 2026, 2–5 p.m. or 7–10 p.m. · One Day Only
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopChicago Gourmet: Grand Cru
Acclaimed chefs, winemakers and mixologists pair luxury bites and pours in two rooftop sessions.
Add to calendar#13
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopSunday, September 27, 2026, noon–3 p.m.Ticketed via Chicago Gourmet
Chicago Gourmet: Rise & Shine Gourmet
Art Smith and Erick Williams host a Southern-style rooftop brunch with cocktails.
One Day Only
#13Sunday, September 27, 2026, noon–3 p.m. · One Day Only
Harris Theater Rooftop, the Loop, Downtown, the Loop & West LoopChicago Gourmet: Rise & Shine Gourmet
Art Smith and Erick Williams host a Southern-style rooftop brunch with cocktails.
Add to calendar#14
Studebaker Theater, Downtown, the Loop & West LoopThrough Sep 27, 2026
Lucy Darling – Chicago, IL – Simply Darling Tour
Award-winning magician-comedian Lucy Darling, a 1940s-style socialite, plays intimate live shows.
One Weekend Only
#14Through Sep 27, 2026 · One Weekend Only
Studebaker Theater, Downtown, the Loop & West LoopLucy Darling – Chicago, IL – Simply Darling Tour
Award-winning magician-comedian Lucy Darling, a 1940s-style socialite, plays intimate live shows.
Add to calendar#15
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopSunday, September 27, 2026, 7 p.m.$37.95
Tim Convy & Sean O'Brien at Zanies Chicago
Tim Convy & Sean O'Brien at Zanies Chicago has enough weekend energy to earn a spot on the board.
Limited Run
#15Sunday, September 27, 2026, 7 p.m. · Limited Run
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopTim Convy & Sean O'Brien at Zanies Chicago
Tim Convy & Sean O'Brien at Zanies Chicago has enough weekend energy to earn a spot on the board.
Add to calendar#16
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopThursday through Saturday, September 24–26, 2026; 7 p.m. nightly plus 9:15 p.m. late shows Friday and Saturday$43
Cliff Cash at Zanies Chicago
Cliff Cash at Zanies Chicago has enough weekend energy to earn a spot on the board.
One Weekend Only
#16Thursday through Saturday, September 24–26, 2026; 7 p.m. nightly plus 9:15 p.m. late shows Friday and Saturday · One Weekend Only
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopCliff Cash at Zanies Chicago
Cliff Cash at Zanies Chicago has enough weekend energy to earn a spot on the board.
Add to calendar#17
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
#17Extended 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#18
Gene Siskel Film Center, Downtown, the Loop & West LoopSaturday, September 26 at 4 p.m.; Sunday, September 27 at 2 p.m.
The Sacrifice
The Sacrifice has enough weekend energy to earn a spot on the board.
One Weekend Only
#18Saturday, September 26 at 4 p.m.; Sunday, September 27 at 2 p.m. · One Weekend Only
Gene Siskel Film Center, Downtown, the Loop & West Loop#19
The Comedy Bar, Downtown, the Loop & West LoopSun, Sep 27, 2026 · 6:30pm$25 – $35
Jay Washington at The Comedy Bar
Jay Washington at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#19Sun, Sep 27, 2026 · 6:30pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopJay Washington at The Comedy Bar
Jay Washington at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#20
Gene Siskel Film Center, Downtown, the Loop & West Loop#20Saturday 2pm · Limited Run
Gene Siskel Film Center, Downtown, the Loop & West Loop#21
Hilton Chicago, Downtown, the Loop & West LoopSat, Sep 26, 2026 · 3:00pmFree
Mini Film & Play Fest on Expo Day 2: Reel Stories, Real Vision
Mini Film & Play Fest on Expo Day 2: Reel Stories, Real Vision has enough weekend energy to earn a spot on the board.
FreeOne Day Only
#21Sat, Sep 26, 2026 · 3:00pm · One Day Only
Hilton Chicago, Downtown, the Loop & West LoopMini Film & Play Fest on Expo Day 2: Reel Stories, Real Vision
Mini Film & Play Fest on Expo Day 2: Reel Stories, Real Vision has enough weekend energy to earn a spot on the board.
Add to calendar#22
The Comedy Bar, Downtown, the Loop & West LoopSun, Sep 27, 2026 · 8:30pm$25 – $35
Mike Samp at The Comedy Bar
Mike Samp at The Comedy Bar has enough weekend energy to earn a spot on the board.
One Day Only
#22Sun, Sep 27, 2026 · 8:30pm · One Day Only
The Comedy Bar, Downtown, the Loop & West LoopMike Samp at The Comedy Bar
Mike Samp at The Comedy Bar has enough weekend energy to earn a spot on the board.
Add to calendar#23
The Lion Theatre, 182 N Wabash Ave, Downtown, the Loop & West LoopFri, Sep 25, 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
#23Fri, Sep 25, 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#24
Gene Siskel Film Center, Downtown, the Loop & West LoopFriday, September 25 at 6 p.m.; Saturday, September 26 at 8 p.m.
The Oldest Person in the World
The Oldest Person in the World has enough weekend energy to earn a spot on the board.
One Weekend Only
#24Friday, September 25 at 6 p.m.; Saturday, September 26 at 8 p.m. · One Weekend Only
Gene Siskel Film Center, Downtown, the Loop & West LoopThe Oldest Person in the World
The Oldest Person in the World has enough weekend energy to earn a spot on the board.
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