Stumblday calendar · Chicago
Date Night Ideas in Chicago
Follow Date Night Ideas in Chicago and its events show up in Your events. No emails unless you ask.
This calendar gathers evening plans across Chicago that work well for a date. You will find a rotating mix of live music, independent film screenings, comedy sets, and cultural performances around town. The list updates continuously as local venues and organizers announce new shows, making it an easy place to start when planning a night out together.
Hand-picked by Stumblday. Pulled from each week’s Chicago board, where every listing is checked against the organizer’s own page.
Upcoming · 56
Sunday, Oct 4
Wallace & Gromit: The Curse of the Were-Rabbit
2 PM
FACETS Film Forum, Lincoln Park, Lakeview & Wrigleyville
Parkinson’s Foundation Special Event
4 PM
Zanies Comedy Club, Old Town, Downtown, the Loop & West Loop
Legs Will Be Broken: A Play, Improvised
7 PM
Judy’s Beat Lounge at the Second City Training Center, Lincoln Park, Lakeview & Wrigleyville
Watch What Crappens – Chicago, IL – In The Mix Tour
7:30 PM
The Vic Theatre, Lincoln Park, Lakeview & Wrigleyville
Friday, Oct 9
The Heart of the Story at Douglass
6 PM
Douglass Park, North Lawndale, Pilsen, West Town & the West Side
Music Theater Works Presents: Escape to Margaritaville
7 PM
North Theatre at North Shore Center for the Performing Arts, 9501 Skokie Blvd, Evanston & Oak Park
(dark) Toilet Fire (matter(s))
7:30 PM
Northwestern University Chicago Campus – Abbott Hall Wirtz Theatre, Downtown, the Loop & West Loop
Carrie Nation and the Speakeasy, the Fabulous Cowboys
9 PM
Reggies Music Joint, 2105 South State Street, Downtown, the Loop & West Loop
Godfrey
9:30 PM
Chicago Improv - Schaumburg, 5 Woodfield Mall K 120B, Schaumburg, IL 60173, Far Suburbs
Saturday, Oct 10
Music Box of Horrors: Possession, In the Mouth of Madness & Event Horizon
6:45 PM
Music Box Theatre, Lakeview
Dance Divas 2026: “Everything Old Is New Again”
8 PM
The Rhapsody Theater, Andersonville, Uptown & Lincoln Square
