#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 the Weekend of Oct 9–12, 2026
Stumblday's hand-checked ranking of the best date night in Chicago the weekend of Oct 9–12, 2026: 93 picks, refreshed weekly.
93 picks · checked Sep 21
93 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
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
#6Friday 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.
Add to calendar#7
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
#7Saturday, 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#8
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
#8September 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#9
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
#9Through 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#10
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
#10Saturday, 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#11
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsMon, Oct 12, 2026 · 7:30pm
Simple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
One Day Only
#11Mon, Oct 12, 2026 · 7:30pm · One Day Only
Historic Main Stage at Athenaeum Center, Lincoln Park, Lakeview & WrigleyvilleKeiko Oikawa · Public domain · Wikimedia CommonsSimple TOO Live: An Evening with Yotam Ottolenghi
Chef Yotam Ottolenghi talks through his new cookbook, the follow-up to Ottolenghi Simple, live.
Add to calendar#12
Lookingglass Theatre, The Joan and Paul Theatre, Streeterville, Downtown, the Loop & West LoopChris Rycroft · CC BY 2.0 · Wikimedia CommonsSaturday, October 10, 2026 · 2 PM audio-described performanceTicketed via Lookingglass The…
Kowalski
Johnny Galecki stars in this limited engagement about Williams meeting Brando.
One Day Only
#12Saturday, October 10, 2026 · 2 PM audio-described performance · One Day Only
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#13
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
#13Sat, 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#14
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleSunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM$20 individual programs
Cinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
One Weekend Only
#14Sunday–Monday, October 11–12, 2026 · Sun 7–10 PM; Mon 5–11 PM · One Weekend Only
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleCinema Femme Short Film Festival 2026
The festival opens Sunday, then pairs a panel with two shorts programs.
Add to calendar#15
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
#15Fri, 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#16
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
#16Saturdays 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#17
The Second City, Lincoln Park, Lakeview & WrigleyvilleOpen runTickets starting at $45
Pandemonium, Please Hold
The Second City's 114th Mainstage revue is a loud, fast six-person comedy show.
Limited Run
#17Open run · Limited Run
The Second City, Lincoln Park, Lakeview & WrigleyvillePandemonium, Please Hold
The Second City's 114th Mainstage revue is a loud, fast six-person comedy show.
#18
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleMonday, October 12, 2026 · 7 PM; post-film director Q&A$15 general admission
Begotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Limited Run
#18Monday, October 12, 2026 · 7 PM; post-film director Q&A · Limited Run
Music Box Theatre, Southport Corridor, Lakeview, Lincoln Park, Lakeview & WrigleyvilleBegotten: New Restoration with E. Elias Merhige
A new 4K restoration screens with director E. Elias Merhige in person for a Q&A.
Add to calendar#19
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
#19Fri, 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#20
Park West, Lincoln Park, Lakeview & WrigleyvilleSun, Oct 11, 2026 · 7:00pm
Kanan Gill: Not This Again
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
One Day Only
#20Sun, Oct 11, 2026 · 7:00pm · One Day Only
Park West, Lincoln Park, Lakeview & WrigleyvilleKanan Gill: Not This Again
Comedian Kanan Gill brings a brand-new stand-up show to Park West.
Add to calendar#21
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
#21September 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#22
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
#22Friday, 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#23
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
#23Fri, 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#24
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
#24August 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