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Things to Do in Chicago — September 2026
Explore 411 upcoming things to do in Chicago in September 2026, including ChiTown Drive-In Presents - Obsession (2026) and Chicago Architecture Center River…
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411 things to do
Showing 1–24 of 411 · Chicago
Wed, Sep 2, 202611:00 AM
Family · Chicago
Balloon Museum | EmotionAir - Art You Can Feel - Chicago
Check ticketsBalloon Museum
Wed, Sep 2, 20267:00 PM
Concert · Chicago
Depaul Blue Demons Womens Volleyball vs. Portland State Vikings Womens Volleyball
Check ticketsDepaul Blue Demons Womens Volleyball
Wed, Sep 2, 20267:00 PM
Theatre & Show · Chicago
Drunk Shakespeare: Drunk Romeo & Juliet (21+ Event)
Check ticketsDrunk Shakespeare
Wed, Sep 2, 20268:00 PM
Event · Chicago
ChiTown Drive-In Presents - Ferris Bueller's Day Off
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Wed, Sep 2, 20268:00 PM
Theatre & Show · Chicago
The Second City's: Pandemonium, Please Hold
Check ticketsSecond City
Wed, Sep 2, 202610:15 PM
Seasonal Event · Chicago
ChiTown Drive-In Presents - Halloween (the 1978 Original!)
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Thu, Sep 3, 202611:00 AM
Family · Chicago
Balloon Museum | EmotionAir - Art You Can Feel - Chicago
Check ticketsBalloon Museum
Thu, Sep 3, 20266:30 PM
Concert · Chicago
ISAIAH RASHAD: Lil Sunny's Awful Road Trip
Check ticketsIsaiah Rashad
Thu, Sep 3, 20267:00 PM
Theatre & Show · Chicago
Drunk Shakespeare: Drunk Romeo & Juliet (21+ Event)
Check ticketsDrunk Shakespeare
Thu, Sep 3, 20267:30 PM
Theatre & Show · Chicago
Vape! The Grease Parody
Check ticketsVape! The Grease Parody
Local event guide
Chicago event calendar
Browse events, shows and things to do in Chicago in September 2026. Compare dates, venues and start times, then open an event for current ticket information and nearby planning options.
411 things to do in this calendar; current dates span Sep 1–3, 2026; highlights include ChiTown Drive-In Presents - Obsession (2026) and Chicago Architecture Center River Cruise Aboard First Lady. Use the date and category links on this page when you want a narrower plan.
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Explore 411 upcoming things to do in Chicago in September 2026, including ChiTown Drive-In Presents - Obsession (2026) and Chicago Architecture Center River…
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