#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 Chicago Friday Night, Columbus Day Weekend 2026
18 picks
The 10 best date night picks in Chicago on Friday night, Oct 9
- Jerry Seinfeld Live! — Fri, Oct 9 7pm; Sat, Oct 10 · 5pm and 8pm · Downtown
- Lincoln Park Wine Fest — October 9–11; Friday 5–10pm · General admission from $30 · Lincoln Park
- Music Theater Works Presents: Escape to Margaritaville — Fri, Oct 9 7 PM; Sat, Oct 10 · 7:30 PM; Sun · 9501 Skokie Blvd
- Robby Hoffman – Live on Tour — Fri, Oct 9 7:00pm · Lincoln Park
- The Heart of the Story at Douglass — Friday, October 9 6–8 PM · Free · Pilsen
- The Factory Theater Presents the World Premiere of “Radical Futures” — Oct 9–Oct 18, 2026 · $30 · The Factory Theater
- No Skin Off My Ass — Friday 9:30pm · Lincoln Park
- Paul Elia at The Comedy Bar — Fri, Oct 9 7:00pm · $25 – $35 · Downtown
- Super 8½ — Friday 7pm · Lincoln Park
- Phil Hanley — Fri, Oct 9 7:15pm · Logan Square
#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
Jonquil Park, Lincoln ParkWarren 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
Jonquil Park, Lincoln Park
The 10th Lincoln Park Wine Fest pours in two-hour sessions in a small neighborhood park; 21+.
One Weekend Only
#2October 9–11, 2026; Friday 5–10pm, Saturday 11am–10pm, Sunday 11am–7pm · One Weekend Only
Jonquil Park, Lincoln ParkWarren 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#3
Fri, Oct 9 · 7 PM; Sat, Oct 10 · 7:30 PM; Sun, Oct 11 · 2 PM
Music Theater Works Presents: Escape to Margaritaville
9501 Skokie Blvd, Evanston & Oak Park
Music Theater Works stages Escape to Margaritaville at the North Shore Center.
One Weekend Only
#3Fri, 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#4
The Vic Theatre, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 7:00pm
Robby Hoffman – Live on Tour
Lincoln Park, Lakeview & Wrigleyville
Comedian Robby Hoffman brings a headlining stand-up tour to the Vic Theatre.
One Day Only
#4Fri, 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#5
Douglass Park, North Lawndale, Pilsen, West Town & the West SideFriday, October 9, 2026 · 6–8 PMFREE
The Heart of the Story at Douglass
Pilsen, West Town & the West Side
Cerqua Rivera’s Dance Ensemble and Jazz Orchestra lead a free all-ages performance.
FreeOne Day Only
#5Friday, 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#6
The Factory TheaterOct 9, 2026–Oct 18, 2026$30
The Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater
The Factory Theater Presents the World Premiere of “Radical Futures” is listed for Chicago this.
Limited Run
#6Oct 9, 2026–Oct 18, 2026 · Limited Run
The Factory TheaterThe Factory Theater Presents the World Premiere of “Radical Futures”
The Factory Theater Presents the World Premiere of “Radical Futures” is listed for Chicago this.
Add to calendar#7
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleFriday 9:30pm
No Skin Off My Ass
Lincoln Park, Lakeview & Wrigleyville
No Skin Off My Ass has enough weekend energy to earn a spot on the board.
One Day Only
#7Friday 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#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
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleFriday 7pm
Super 8½
Lincoln Park, Lakeview & Wrigleyville
Super 8½ has enough weekend energy to earn a spot on the board.
One Day Only
#9Friday 7pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville#10
The Den Theatre, 1331 N Milwaukee Ave, Logan Square, Wicker Park & BucktownFri, Oct 9, 2026 · 7:15pm
Phil Hanley
Logan Square, Wicker Park & Bucktown
Phil Hanley has enough weekend energy to earn a spot on the board.
One Day Only
#10Fri, Oct 9, 2026 · 7:15pm · One Day Only
The Den Theatre, 1331 N Milwaukee Ave, Logan Square, Wicker Park & BucktownMore on Friday night
#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
The Space at RockwellFri, Oct 16, 2026 · 8:00 PM$45
T A K E
The Space at Rockwell
T A K E has enough weekend energy to earn a spot on the board.
Limited Run
#12Fri, Oct 16, 2026 · 8:00 PM · Limited Run
The Space at Rockwell#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 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
#14Friday 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.
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#15
iO Theater, Lincoln Park, Lakeview & WrigleyvilleFri, Oct 9, 2026 · 9:30pm$45
Wine Down Comedy
Lincoln Park, Lakeview & Wrigleyville
Wine Down Comedy has enough weekend energy to earn a spot on the board.
One Day Only
#15Fri, Oct 9, 2026 · 9:30pm · One Day Only
iO Theater, Lincoln Park, Lakeview & WrigleyvilleWine Down Comedy
Wine Down Comedy has enough weekend energy to earn a spot on the board.
Add to calendar#16
Fri, Oct 9, 2026 · 9:30pm
Godfrey
IL 60173, Far Suburbs
Comedian Godfrey does stand-up at Chicago Improv in Schaumburg.
One Day Only
#16Fri, Oct 9, 2026 · 9:30pm · One Day Only
#17
The Comedy Vault, 18 E. Wilson Street, Far SuburbsFri, Oct 9, 2026 · 7:00pm
Yannis Pappas
18 E. Wilson Street, Far Suburbs
Yannis Pappas has enough weekend energy to earn a spot on the board.
One Day Only
#17Fri, Oct 9, 2026 · 7:00pm · One Day Only
The Comedy Vault, 18 E. Wilson Street, Far Suburbs#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 Chicago on Friday night of Columbus Day weekend, Oct 9: 18 picks, refreshed weekly.
