#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 Chicago Friday Night, Oct 9
Stumblday's hand-checked ranking of the best date night in Chicago on Friday night, Oct 9: 30 picks, refreshed weekly.
30 picks · checked Sep 21
30 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
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:30pm
Topdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Limited Run
#2Fri, Oct 9, 2026 · 7:30pm · Limited Run
Steppenwolf Downstairs Theater, Lincoln Park, Lakeview & WrigleyvilleTopdog/Underdog
Topdog/Underdog follows brothers Lincoln and Booth, getting by in America, at Steppenwolf.
Add to calendar#3
Jonquil Park, Lincoln Park, Lakeview & WrigleyvilleWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsOctober 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pmGeneral admission from $30
Lincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#3October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln Park, Lakeview & WrigleyvilleWarren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia CommonsLincoln Park Wine Fest
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
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
Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM
Music Theater Works Presents: Escape to Margaritaville
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
One Weekend Only
#5Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM · One Weekend Only
Music Theater Works Presents: Escape to Margaritaville
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
Add to calendar#6
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:00pm
Robby Hoffman – Live on Tour
Comedian Robby Hoffman brings a headlining stand-up tour to the Vic Theatre.
One Day Only
#6Fri, Oct 9, 2026 · 7:00pm · One Day Only
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleRobby Hoffman – Live on Tour
Comedian Robby Hoffman brings a headlining stand-up tour to the Vic Theatre.
Add to calendar#7
Douglass Park, North Lawndale, Pilsen, West Town & the West SideFriday, October 9, 2026 · 6–8 PMFREE
The Heart of the Story at Douglass
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
FreeOne Day Only
#7Friday, October 9, 2026 · 6–8 PM · One Day Only
Douglass Park, North Lawndale, Pilsen, West Town & the West SideThe Heart of the Story at Douglass
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
Add to calendar#8
The Factory Theater, Andersonville, Uptown & Lincoln SquareFri, Oct 9, 2026 · 7:30pm$30
The Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater Presents the World Premiere of “Radical Futures” has enough weekend energy to earn a spot on the board.
One Weekend Only
#8Fri, Oct 9, 2026 · 7:30pm · One Weekend Only
The Factory Theater, Andersonville, Uptown & Lincoln SquareThe Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater Presents the World Premiere of “Radical Futures” has enough weekend energy to earn a spot on the board.
Add to calendar#9
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleFriday 9:30pm
No Skin Off My Ass
No Skin Off My Ass has enough weekend energy to earn a spot on the board.
One Day Only
#9Friday 9:30pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleNo Skin Off My Ass
No Skin Off My Ass has enough weekend energy to earn a spot on the board.
Add to calendar#10
Oil Lamp Theater, Evanston & Oak ParkFri, Oct 9, 2026 · 7:30pm$55
Oil Lamp Theater Presents “Dial M for Murder”
Oil Lamp Theater Presents “Dial M for Murder” has enough weekend energy to earn a spot on the board.
One Weekend Only
#10Fri, Oct 9, 2026 · 7:30pm · One Weekend Only
Oil Lamp Theater, Evanston & Oak ParkOil Lamp Theater Presents “Dial M for Murder”
Oil Lamp Theater Presents “Dial M for Murder” has enough weekend energy to earn a spot on the board.
Add to calendar#11
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
#11Fri, 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#12
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#12Friday 7pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#13
The Den Theatre, 1331 N Milwaukee Ave, Logan Square, Wicker Park & BucktownFri, Oct 9, 2026 · 7:15pm
Phil Hanley
Phil Hanley has enough weekend energy to earn a spot on the board.
Limited Run
#13Fri, Oct 9, 2026 · 7:15pm · Limited Run
The Den Theatre, 1331 N Milwaukee Ave, Logan Square, Wicker Park & Bucktown#14
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
#14Fri, 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#15
Facility Theatre, Logan Square, Wicker Park & BucktownSeptember 20–October 26, 2026; times and venues varyPay what you can
37th Annual Rhinoceros Theater Festival
37th Annual Rhinoceros Theater Festival has enough weekend energy to earn a spot on the board.
Limited Run
#15September 20–October 26, 2026; times and venues vary · Limited Run
Facility Theatre, Logan Square, Wicker Park & Bucktown37th Annual Rhinoceros Theater Festival
37th Annual Rhinoceros Theater Festival has enough weekend energy to earn a spot on the board.
Add to calendar#16
The Space at Rockwell, Lincoln Park, Lakeview & WrigleyvilleOctober 9–25, 2026$45
T A K E
T A K E has enough weekend energy to earn a spot on the board.
Limited Run
#16October 9–25, 2026 · Limited Run
The Space at Rockwell, Lincoln Park, Lakeview & Wrigleyville#17
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
#17Friday 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#18
The Second City, Lincoln Park, Lakeview & WrigleyvilleOpen run
Best of the Second City
A greatest-hits revue from the comedy theater that launched Tina Fey and Steve Carell.
Limited Run
#18Open run · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvilleBest of the Second City
A greatest-hits revue from the comedy theater that launched Tina Fey and Steve Carell.
Add to calendar#19
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
#19Fri, 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#20
iO Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:30pm$22
Devil’s Daughter
Devil’s Daughter has enough weekend energy to earn a spot on the board.
One Day Only
#20Fri, Oct 9, 2026 · 7:30pm · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvilleDevil’s Daughter
Devil’s Daughter has enough weekend energy to earn a spot on the board.
Add to calendar#21
The Annoyance Theatre, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 8:00pm$15
Missed Call Sketch Comedy Show
Missed Call writes and performs a brand-new sketch show inspired by an audience suggestion.
One Day Only
#21Fri, Oct 9, 2026 · 8:00pm · One Day Only
The Annoyance Theatre, Lincoln Park, Lakeview & WrigleyvilleMissed Call Sketch Comedy Show
Missed Call writes and performs a brand-new sketch show inspired by an audience suggestion.
Add to calendar#22
Stars and Garters Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 10:00pm
Rising Stars Burlesque Revue
Rising Stars Burlesque Revue has enough weekend energy to earn a spot on the board.
One Day Only
#22Fri, Oct 9, 2026 · 10:00pm · One Day Only
Stars and Garters Theater, Lincoln Park, Lakeview & WrigleyvilleRising Stars Burlesque Revue
Rising Stars Burlesque Revue has enough weekend energy to earn a spot on the board.
Add to calendar#23
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
#23Friday 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#24
iO Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 9:30pm$15
Kohl’s Cash: Tgif (That’s Good Improv Friday)
iO house team Kohl's Cash builds a fully original improv show from audience suggestions.
One Day Only
#24Fri, Oct 9, 2026 · 9:30pm · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvilleKohl’s Cash: Tgif (That’s Good Improv Friday)
iO house team Kohl's Cash builds a fully original improv show from audience suggestions.
Add to calendar