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Hand-picked every week — checked against organizers’ own pages.
Stumblday's ranked list of the best date night in Chicago tomorrow, Thursday, October 29 — hand-curated and refreshed daily.
16 picks · checked Oct 28
Albany Park, Andersonville, Uptown & Lincoln SquareAndersonville, Uptown & Lincoln Square
Only 28 guests at a time enter an Albany Park warehouse for this immersive final-season opening.
Albany Park, Andersonville, Uptown & Lincoln SquareOnly 28 guests at a time enter an Albany Park warehouse for this immersive final-season opening.
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Jazz ShowcaseJazz Showcase
The influential jazz guitarist opens a four-night quintet residency at Jazz Showcase.
Jazz ShowcaseThe influential jazz guitarist opens a four-night quintet residency at Jazz Showcase.
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Cadillac Palace, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
The Book of Mormon plays a 7 PM Thursday performance at the Cadillac Palace.
Cadillac Palace, Downtown, the Loop & West LoopThe Book of Mormon plays a 7 PM Thursday performance at the Cadillac Palace.
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George Van Dusen Theatre at North Shore Center, 9501 Skokie Blvd, Evanston & Oak Park9501 Skokie Blvd, Evanston & Oak Park
The United European Ballet Company brings Cinderella to Skokie for a 7 PM performance.
George Van Dusen Theatre at North Shore Center, 9501 Skokie Blvd, Evanston & Oak ParkThe United European Ballet Company brings Cinderella to Skokie for a 7 PM performance.
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The Second City, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Comedy show at The Second City October 29 at. Listed on The Second City's official calendar.
The Second City, Lincoln Park, Lakeview & WrigleyvilleComedy show at The Second City October 29 at. Listed on The Second City's official calendar.
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Gene Siskel Film Center, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Screening at Gene Siskel Film Center October 29 at. Listed on Gene Siskel Film Center's official calendar.
Gene Siskel Film Center, Downtown, the Loop & West LoopScreening at Gene Siskel Film Center October 29 at. Listed on Gene Siskel Film Center's official calendar.
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Gene Siskel Film Center, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Screening at Gene Siskel Film Center October 29 at 6 PM. Listed on Gene Siskel Film Center's official calendar.
Gene Siskel Film Center, Downtown, the Loop & West LoopScreening at Gene Siskel Film Center October 29 at 6 PM. Listed on Gene Siskel Film Center's official calendar.
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Theater Wit, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Babes With Blades stages King Lear at Theater Wit with fight choreography by Jess Pennachio.
Theater Wit, Lincoln Park, Lakeview & WrigleyvilleBabes With Blades stages King Lear at Theater Wit with fight choreography by Jess Pennachio.
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FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
A 95-minute drama follows two refugee-camp brothers making comedy sketches and dreaming of zombie films.
FACETS Film Forum, Lincoln Park, Lakeview & WrigleyvilleA 95-minute drama follows two refugee-camp brothers making comedy sketches and dreaming of zombie films.
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Gene Siskel Film Center, Downtown, the Loop & West LoopDowntown, the Loop & West Loop
Cristian Mungiu’s 2026 multilingual drama screens digitally at the Siskel Film Center.
Gene Siskel Film Center, Downtown, the Loop & West LoopCristian Mungiu’s 2026 multilingual drama screens digitally at the Siskel Film Center.
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Second City-Chicago: Mainstage, 1616 N. Wells St., Lincoln Park, Lakeview & WrigleyvilleLincoln Park, Lakeview & Wrigleyville
Second City’s Mainstage presents Pandemonium, Please Hold night.
Second City-Chicago: Mainstage, 1616 N. Wells St., Lincoln Park, Lakeview & WrigleyvilleSecond City’s Mainstage presents Pandemonium, Please Hold night.
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Annoyance Theatre & BarAnnoyance Theatre & Bar
Comedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
Annoyance Theatre & BarComedy Hour at Annoyance Theatre at Annoyance Theatre & Bar.
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Aguijón TheaterAguijón Theater
I.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival at Aguijón.
Aguijón TheaterI.A. Inteligencia Actoral – Destinos: 9th Chicago International Latino Theater Festival at Aguijón.
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KermessKermess
Premonitions Inc. at Kermess at Kermess.
KermessFriday at 5pm, one email. Unsubscribe anytime.
Music Box Theatre, LakeviewMusic Box Theatre, Lakeview
Music Box of Horrors: The Final Chapter is listed for Chicago this weekend.
Music Box Theatre, LakeviewMusic Box of Horrors: The Final Chapter is listed for Chicago this weekend.
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Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln SquareAndersonville, Uptown & Lincoln Square
A Strange Loop is listed for Chicago this weekend.
Raven Theatre, Edgewater, Andersonville, Uptown & Lincoln Square
