Arts in the Dark
Photograph: Neal O'Bryan
Photograph: Neal O'Bryan

The best October 2026 events in Chicago

Plot out your October in Chicago with our calendar of things to do, including the best festivals and Halloween parties.

Shannon Shreibak
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The official start of fall in Chicago might be in September, but the season doesn't really hit its stride until October—a month replete with crisp air, colorful fall foliage and a heaping helping of spooky fun. Take advantage of everything autumn has to offer by exploring the best pumpkin patches near Chicago, attending an apple-themed neighborhood fest, getting lost in corn mazes or staring up at the changing leaves at your local park or garden. And of course, celebrate Halloween in Chicago with spooky pop-ups, haunted houses, horror movie marathons and even more ghoulish events. Ready to embrace autumn? Check out the rest of the best things do to in Chicago this October. 

RECOMMENDED: Events calendar for Chicago in 2026

Time Out Market Chicago

We've rounded up the best chefs in the city to join us at Time Out Market Chicago, a culinary and cultural destination in the heart of Fulton Market featuring more than 15 kitchens, three bars and one drop-dead gorgeous rooftop terrace—all spread across three floors.

Best Chicago events in October 2026

  • Things to do
Celebrating Chicago culture through couture, Chicago Fashion Week brings runway shows, markets, educational programs and more—many of which are free to attend—throughout the city. The full gamut of programming is yet to be announced; stay updated via CFW's website. 

GYG Chicago TTD

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