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

The best October 2024 events in Chicago

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

Jeffy Mai
Edited by Jeffy Mai
Editor, Time Out Chicago
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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: Check out our 2024 Chicago events calendar

Time Out Market Chicago

Time Out Market Chicago

Time Out Market Chicago
Photograph: Jaclyn Rivas for Time Out

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 2025

The Paper Machete

  • Comedy
  • Uptown
  • Recommended
The Paper Machete
The Paper Machete
Photograph: Sarah Larson
This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.

360 Sky Yoga

  • Sports and fitness
  • Yoga & Pilates
  • Streeterville
  • price 2 of 4
  • Recommended
360 Sky Yoga
360 Sky Yoga
Photograph: Courtesy 360 CHICAGO
Head to 360 Chicago on Saturdays for yoga with a killer view. Instructor Britta Eumann will lead an hour-long class on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Center) that’s suitable for all ages and skill levels—you just need to bring your own mat and arrived properly dressed. Registration is $55 and includes a cocktail or coffee, plus admission to the observation deck so you can stick around and snap some photos after you're done striking poses on the mat.
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WONDRA

  • Things to do
  • Suburbs
WONDRA
WONDRA
Photograph: Courtesy WONDRA
Just when you thought the state's largest mall couldn't surprise you anymore, Woodfield Mall announces WONDRA, a sprawling new immersive experience. Inside, you’ll wander through enchanted meadows that respond to the sound of your voice, stumble across bioluminescent landscapes and drift into crystal caves and celestial gardens that blur the line between digital spectacle and raw wonder. Every corner is crafted to ignite curiosity and inspire a sense of awe we, whether you’re a kid seeing it all for the first time or an adult who forgot what it feels like to play.
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Escape the Museum

  • Things to do
  • Hyde Park
Escape the Museum
Escape the Museum
Photograph: Courtesy of Griffin Museum of Science and Industry
Get ready to unleash your inner Nancy Drew: Escape the Museum is returning to the Griffin Museum of Science and Industry. Participants will journey through a world of mystery, where each exhibit holds clues that lead closer to victory—and the honor of being crowned a member of the Guild of Alchemists. Designed for ages eight and up, the puzzles are engaging for the whole family, while also making this a perfect outing for couples and large groups. The escape room’s runtime averages 50 to 90 minutes, though puzzle-solving prowess may shorten or extend your stay in the museum.
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Sushi Making Class at Sunda

  • Things to do
  • River North
Sushi Making Class at Sunda
Sushi Making Class at Sunda
Photograph: Courtesy Sunda New Asian
Learn how to make your own traditional maki rolls with an interactive class at Sunda. Expert chefs will guide you through the process of assembling temaki (hand-rolled sushi), futomaki (fat-rolled sushi) and uramaki (inside-out rolled sushi) using seaweed wraps, rice, spicy tuna and more. Classes are available at the Fulton Market and River North locations.    
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Lincoln Square Ravenswood Apple Fest

  • Things to do
  • Festivals
  • Lincoln Square
Lincoln Square Ravenswood Apple Fest
Lincoln Square Ravenswood Apple Fest
Photograph: Dan Kasberger
This annual fall street festival returns to Lincoln Square for one apple-filled weekend. Shop autumnal goods at the festival's marketplace, munch on apple-stuffed tamales and apple doughnuts from local restaurants, sip cider and apple-flavored beer, catch live music performances and bring the kids for seasonal activities—you won't find many better ways to welcome autumn. For more fall fun, check out our guide to the best orchards for apple-picking near Chicago.

La Vita Spritz

  • Things to do
  • West Loop
La Vita Spritz
La Vita Spritz
Photograph: Kevin Serna
As if you needed an excuse to spend golden hour at Time Out Market Chicago's rooftop bar—we're hosting a very special happy hour until the cold snap arrives. Sip on vibrant spritz drink specials crafted for summer lounging, complete with a live DJ spinning feel-good vibes all evening long. Whether you're here to dance, chill or just toast to the moment, this is your chance to savor the season.
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Night of 1,000 Jack-o’-Lanterns

  • Attractions
  • Parks and gardens
  • Suburbs
Night of 1,000 Jack-o’-Lanterns
Night of 1,000 Jack-o’-Lanterns
Photograph: Courtesy Chicago Botanic Garden
Get in the holiday spirit at this annual ghoulish makeover of the Chicago Botanic Garden. The event brings together more than 1,000 real pumpkins—some weighing up to 150 pounds—which are LED-lit creations and staged along the garden's pathway where other entertaining characters and activations await visitors. Seasonal snacks and drinks are available for purchase, in case all that wandering makes you hungry. 
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World Music Festival Chicago

  • Music
  • Latin and world
  • Loop
World Music Festival Chicago
World Music Festival Chicago
Photograph: Patrick L. Pyszka
Explore music from around the globe during this annual festival, now in its 24th year, which brings a wide array of performers to venues across the city for free musical performances. Experience sounds and subgenres from regions like Brazil, South Korea, Senegal and more. For a full list of performances, visit the festival's website. 
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