#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 Saturday Night, Oct 10
Stumblday's hand-checked ranking of the best date night in Chicago on Saturday night, Oct 10: 44 picks, refreshed weekly.
44 picks · checked Sep 21
44 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
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
#4Fri, 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.
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#5
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
#5October 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#6
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleBrandon Olafsson · CC BY 2.0 · Wikimedia CommonsSaturday, October 10, 2026, 6:45 PM$13 for most screenings
Music Box of Horrors: Possession, In the Mouth of Madness & Event Horizon
One ticket covers a horror triple bill, two films on 35mm, running late into the night.
Limited Run
#6Saturday, October 10, 2026, 6:45 PM · Limited Run
Music Box Theatre, Lakeview, Lincoln Park, Lakeview & WrigleyvilleBrandon Olafsson · CC BY 2.0 · Wikimedia CommonsMusic Box of Horrors: Possession, In the Mouth of Madness & Event Horizon
One ticket covers a horror triple bill, two films on 35mm, running late into the night.
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
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsThrough Oct 11, 2026From $34 in person
Mean Girls
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Limited Run
#8Through Oct 11, 2026 · Limited Run
Paramount Theatre, Aurora, Far SuburbsJoseph Gage · CC BY-SA 2.0 · Wikimedia CommonsMean Girls
The Chicago-area premiere of the Tina Fey musical, a big Equity production in Aurora from $34.
Add to calendar#9
The Edge Off Broadway Theatre, Andersonville, Uptown & Lincoln SquareSaturday, October 10, 2026, 8 p.m.$20–$30
Idle Muse Theatre Company Presents “Witch”
Idle Muse Theatre Company stages Jen Silverman's Witch for its 20th season.
One Day Only
#9Saturday, October 10, 2026, 8 p.m. · One Day Only
The Edge Off Broadway Theatre, Andersonville, Uptown & Lincoln SquareIdle Muse Theatre Company Presents “Witch”
Idle Muse Theatre Company stages Jen Silverman's Witch for its 20th season.
Add to calendar#10
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleSat, Oct 10, 2026 · 7:30pm$20–$60
Vladimir
Erika Sheffer's Vladimir follows an independent journalist under a new Russian regime.
One Day Only
#10Sat, Oct 10, 2026 · 7:30pm · One Day Only
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleVladimir
Erika Sheffer's Vladimir follows an independent journalist under a new Russian regime.
Add to calendar#11
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
#11Fri, 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#12
Green Mill Cocktail Lounge, Uptown, Andersonville, Uptown & Lincoln SquareKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsSaturdays at 3pm (doors 1pm); no end date announcedFREE
The Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
FreeLimited Run
#12Saturdays at 3pm (doors 1pm); no end date announced · Limited Run
Green Mill Cocktail Lounge, Uptown, Andersonville, Uptown & Lincoln SquareKenneth C. Zirkel · CC BY-SA 4.0 · Wikimedia CommonsThe Paper Machete
The script is new every week at this free two-hour show in the Green Mill, a bar since 1907.
Add to calendar#13
Northlight Theatre, Evanston, Evanston & Oak ParkSeptember 9 – October 25, 2026 (extended)Ticketed
The Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Limited Run
#13September 9 – October 25, 2026 (extended) · Limited Run
Northlight Theatre, Evanston, Evanston & Oak ParkThe Front Page
The classic Chicago newspaper comedy continues its extended run at Northlight in Evanston.
Add to calendar#14
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
#14Fri, 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#15
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsAugust 19–October 18, 2026Tickets via Drury Lane box of…
The Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Limited Run
#15August 19–October 18, 2026 · Limited Run
Drury Lane Theatre, Oakbrook Terrace, Far SuburbsThe Buddy Holly Story
Buddy Holly’s songs drive this biographical musical at Drury Lane Theatre.
Add to calendar#16
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareOctober 8 – November 8, 2026Tickets via Raven Theatre
A Strange Loop
A Strange Loop has enough weekend energy to earn a spot on the board.
Limited Run
#16October 8 – November 8, 2026 · Limited Run
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square#17
The Second City, Lincoln Park, Lakeview & WrigleyvilleSat, Oct 10, 2026 · 7:30pm$25
Baby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical has enough weekend energy to earn a spot on the board.
One Day Only
#17Sat, Oct 10, 2026 · 7:30pm · One Day Only
The Second City, Lincoln Park, Lakeview & WrigleyvilleBaby Wants Candy! The Original Completely Improvised Musical
Baby Wants Candy! The Original Completely Improvised Musical has enough weekend energy to earn a spot on the board.
Add to calendar#18
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleSaturday 7pm
The Raspberry Reich
The Raspberry Reich has enough weekend energy to earn a spot on the board.
One Day Only
#18Saturday 7pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleThe Raspberry Reich
The Raspberry Reich has enough weekend energy to earn a spot on the board.
Add to calendar#19
Stars and Garters Theater, Lincoln Park, Lakeview & WrigleyvilleSat, Oct 10, 2026 · 7:00pm$40
The Séance: Live (and dead) in Chicago
A theatrical séance recreating 19th-century spirit circles at Stars and Garters.
One Day Only
#19Sat, Oct 10, 2026 · 7:00pm · One Day Only
Stars and Garters Theater, Lincoln Park, Lakeview & WrigleyvilleThe Séance: Live (and dead) in Chicago
A theatrical séance recreating 19th-century spirit circles at Stars and Garters.
Add to calendar#20
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
#20Fri, 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#21
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
#21Fri, 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#22
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleSaturday 5pm
The Misandrists
The Misandrists has enough weekend energy to earn a spot on the board.
One Day Only
#22Saturday 5pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleThe Misandrists
The Misandrists has enough weekend energy to earn a spot on the board.
Add to calendar#23
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
#23Extended 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#24
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleSaturday 9:30pm
Pierrot Lunaire
Pierrot Lunaire has enough weekend energy to earn a spot on the board.
One Day Only
#24Saturday 9:30pm · One Day Only
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvillePierrot Lunaire
Pierrot Lunaire has enough weekend energy to earn a spot on the board.
Add to calendar