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Things to Do in Chicago — October 2026
Explore 42 upcoming things to do in Chicago in October 2026, including Sunday Night Live Ft. Vibe Theory and The Dracula Show Halloween Special with Redder…
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42 things to do
Showing 25–42 of 42 · Chicago
Sun, Oct 25, 20269:00 PM
Concert · Chicago
The Dracula Show Halloween Special with Redder Moon / Corpse Dust / DJ Scary Lady Sarah
$20.39
Sun, Oct 25, 20269:30 PM
Seasonal Event · Chicago
ChiTown Drive-In Presents - Halloween (the 1978 Original!)
Check ticketsChiTown Movies
Sun, Oct 25, 2026Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Tour Experience
Mon, Oct 26, 20261:00 PM
Family · Chicago
Balloon Museum | EmotionAir - Art You Can Feel - Chicago
Check ticketsBalloon Museum
Mon, Oct 26, 20267:00 PM
Event · Chicago
ChiTown Drive-In Presents - Obsession (2026)
Check ticketsChiTown Movies
Mon, Oct 26, 20267:00 PM
Theatre & Show · Chicago
Drunk Shakespeare: Drunk Dracula (21+ Event)
Check ticketsDrunk Shakespeare
Mon, Oct 26, 20267:00 PM
Theatre & Show · Chicago
The Best of The Second City
Check ticketsThe Best of The Second City
Mon, Oct 26, 20267:30 PM
Concert · Chicago
Tedeschi Trucks Band: Future Soul 2026 Tour
Check ticketsTedeschi Trucks Band
Mon, Oct 26, 20269:15 PM
Event · Chicago
ChiTown Drive-In Presents - Nightmare on Elm Street
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Mon, Oct 26, 2026Time TBA
Sports · Chicago
Loyola Ramblers Mens Basketball vs. Calumet College Crimson Wave Mens Basketball
Check ticketsLoyola Ramblers Mens Basketball
Tue, Oct 27, 20261:00 PM
Family · Chicago
Balloon Museum | EmotionAir - Art You Can Feel - Chicago
Check ticketsBalloon Museum
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Explore 42 upcoming things to do in Chicago in October 2026, including Sunday Night Live Ft. Vibe Theory and The Dracula Show Halloween Special with Redder…
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