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Night of 1,000 Jack-o'-Lanterns
Photograph: Courtesy Chicago Botanic Garden

October 2021 events calendar for Chicago

Plot out your October in Chicago with our calendar of things to do, including the best theater and concerts

By Emma Krupp and Zach Long

Welcome to October! The air is crisp, fall foliage in Chicago is about to reach its fiery zenith and it's officially spooky season: What more could you ask for? When you're not busy carving pumpkins and stomping on crunchy leaves this year, take advantage of the many drive-in movie theaters near Chicago, some of which are hosting film fests on everything from international cinema to horror and grindhouse. You can also celebrate Halloween at tons of creepy local attractions, like a path of lit-up jack-o'-lanterns at the Chicago Botanic Gardens. Want to soak up some more time outdoors before temps really plummet? Hop in a car to check out the best pumpkin patches near Chicago, or plan out a walking tour of local architecture with the help of programming from the socially-distanced version of Open House Chicago. Bundle up in your favorite fall sweater and check out our guide to the best things to do in Chicago this October.

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Architecture Cruise
Photograph: Barry Butler

The ultimate list of things to do in Chicago

Things to do

Whether you prefer to pore over iconic artwork in a museum, indulge your epicurean side at top-notch restaurants or see some classic attractions, there's truly something for everyone in Chicago—allow us to point you in the right direction


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