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

The best October 2025 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
Edited by Shannon Shreibak
Things to Do Editor, 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 2025 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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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. 

Open House Chicago

  • Things to do
  • Festivals
  • Loop
  • Recommended
Open House Chicago
Open House Chicago
Photography: Courtesy CC/Unsplash/Dimitry Anikin
Want to get a free, behind-the-scenes look at the Chicago Board of Trade Building, Walt Disney's birthplace home, Orchestra Hall at Symphony Center and more iconic buildings throughout the Chicago area? You’ll have a chance to do so when the Chicago Architecture Center’s annual festival Open House Chicago returns to the city, opening up more than 170 architectural wonders across the city for free tours. 
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Sundays on State

  • Things to do
  • Loop
Sundays on State
Sundays on State
Photograph: Courtesy Chicago Loop Alliance
Sundays on State—which shuts down a strip of State Street spanning from Jackson to Randolph Streets for activations, performances, food and shopping—brings thousands of visitors downtown to check out everything from outdoor dining and browsing opportunities to pop-up karaoke and barre fitness classes. The event returns on two Sundays this year by popular demand. For a full schedule of vendors and events, check out Chicago Loop Alliance's website.

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. For more fall fun, check out our guide to the best orchards for apple-picking near Chicago.
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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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The Rocky Horror Picture Show: The 50th Anniversary Spectacular Tour!

  • Things to do
  • Film events
  • Loop
The Rocky Horror Picture Show: The 50th Anniversary Spectacular Tour!
The Rocky Horror Picture Show: The 50th Anniversary Spectacular Tour!
Photograph: Shutterstock
The Rocky Horror Picture Show's 50th Anniversary Spectacular Tour crash lands at The Chicago Theatre just in time for spooky season. Join the original Brad Majors (Barry Bostwick), Nell Campbell (Nell Campbell) and Magenta (Patricia Quinn) for a screening of the original unedited film like you've never seen it before. Plus, enjoy a live shadow cast with audience participation, a memorabilia display featuring artifacts and actual costumes from the movie, a costume contest and more.
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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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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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