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Things to Do in Chicago — September 2026
Explore 416 upcoming things to do in Chicago in September 2026, including Nate Sib (18+ Event) and The Second City's: Pandemonium, Please Hold. Compare…
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416 things to do
Showing 145–168 of 416 · Chicago
Tue, Sep 8, 20268:00 PM
Theatre & Show · Chicago
The Second City's: Pandemonium, Please Hold
Check ticketsSecond City
Wed, Sep 9, 20261:00 PM
Theatre & Show · Chicago
Kokandy Productions Jekyll & Hyde (Chicago)
Check ticketsKokandy Productions Jekyll & Hyde
Wed, Sep 9, 20266:40 PM
Sports · Chicago
Chicago White Sox vs. Pittsburgh Pirates
Check ticketsChicago White Sox
Wed, Sep 9, 20267:00 PM
Theatre & Show · Chicago
Drunk Shakespeare: Drunk Romeo & Juliet (21+ Event)
Check ticketsDrunk Shakespeare
Wed, Sep 9, 20267:00 PM
Comedy · Chicago
Something Different Presents: Unpopular Opinion Chicago
Check ticketsAnd Now for Something Completely Different
Wed, Sep 9, 20267:30 PM
Sports · Chicago
Chicago Fire FC vs. Inter Miami CF (Rally Towel to 1st 20K)
Check ticketsChicago Fire FC
Wed, Sep 9, 20268:00 PM
Theatre & Show · Chicago
The Second City's: Pandemonium, Please Hold
Check ticketsSecond City
Wed, Sep 9, 20269:00 PM
Nightlife · Chicago
Plantasia Pre-Party with James K / Dorothy Carlos / gs70
$33.17
Thu, Sep 10, 20265:30 PM
Concert · Chicago
Plantasia - Day 1 with Helado Tropical (Helado Negro and Reyna Tropical) / James K / Gigi Masin / Elori Saxl and Henry Solomon +more
Free
Thu, Sep 10, 20266:40 PM
Sports · Chicago
Chicago White Sox vs. Pittsburgh Pirates
Check ticketsChicago White Sox
Thu, Sep 10, 20267:00 PM
Theatre & Show · Chicago
Drunk Shakespeare: Drunk Romeo & Juliet (21+ Event)
Check ticketsDrunk Shakespeare
Thu, Sep 10, 20267:00 PM
Theatre & Show · Chicago
Kokandy Productions Jekyll & Hyde (Chicago)
Check ticketsKokandy Productions Jekyll & Hyde
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Explore 416 upcoming things to do in Chicago in September 2026, including Nate Sib (18+ Event) and The Second City's: Pandemonium, Please Hold. Compare…
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