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Photograph: Courtesy of StarEvents
Photograph: Courtesy of StarEvents

The best September 2026 events in Chicago

Summer is almost over, but September in Chicago is packed with things to do, including festivals, exhibits and concerts.

Shannon Shreibak
Edited by Shannon Shreibak
Things to Do Editor, Chicago
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September might be here, but don't despair—there are still plenty of things to do in Chicago—whether you're still embracing a summertime state of mind or welcoming fall with open arms! From Oktoberfest celebrations to outdoor music festivals (including Riot Fest), we've still got plenty of warm weather fun to take advantage of before the leaves start to turn and the temperature drops. Soak up the sun at the best Chicago beaches and rooftop bars, or spend your weekends checking out the end of festival season at events like the Hyde Park Jazz Festival, Printers Row Lit Fest and Taste of Chicago. And if you really can't wait for fall to arrive, might we suggest some early leaf peeping and apple picking? Whatever your mood, you'll find plenty of ways to keep busy with our roundup of the best things to do in Chicago this September. 

RECOMMENDED: Events calendar for Chicago in 2026

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The best events in Chicago this September

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.

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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Adler at Night

  • Museums
  • Museum Campus
Adler at Night
Adler at Night
Photograph: Courtesy Adler Planetarium
Escape the planet with exhibits about the first lunar missions, the solar system and more, plus immersive shows in the dome theater. Stationed just a stone's throw away from the Adler, the Doane Observatory is also home to the largest public telescope in the area and gathers 7,000 times more light than the human eye. Every Wednesday, the Adler stays open late from 4pm-10pm so that folks can visit after work or school. And best of all, admission is free on those nights for Illinois residents.
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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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Pokémon Fossil Museum

  • Things to do
  • Exhibitions
  • Museum Campus
Pokémon Fossil Museum
Pokémon Fossil Museum
Photograph: Lucy Hewett, Courtesy of The Field Museum,
Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.
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The Infinite Wrench

  • Experimental
  • Uptown
  • price 1 of 4
The Infinite Wrench
The Infinite Wrench
Photograph: Joe Mazza
For more than 30 years, the Neo-Futurists have been delighting late-night crowds with performances that pack 30 miniature plays into a 60-minute show. The company's signature show is more unpredictable than ever these days, with a handful of compact new plays premiering every week. Within the span of 10 minutes, you may be treated to a poignant monologue about everyday life or an irreverent diatribe delivered by a pantsless member of the cast—all inspired by the experiences of the performers on stage. Always changing and evolving, it's the rare show that truly offers something different everytime you show up to see it.
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Drunk Shakespeare Chicago

  • Things to do
  • Performances
  • Loop
  • price 2 of 4
Drunk Shakespeare Chicago
Drunk Shakespeare Chicago
Photograph: Mike Sause
You’ve probably seen a Shakespeare play before, but never like this. Five professional actors come together for each performance of Drunk Shakespeare. The twist? One of them has had five shots before the show and is trying to stay on track while the other four actors do their best to hold the performance together.
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Willem de Kooning Drawing

  • Things to do
  • Exhibitions
  • Grant Park
Willem de Kooning Drawing
Willem de Kooning Drawing
Photograph: John Berens
“Willem de Kooning Drawing” is the first exhibition to explore the full scope of the artist's drawing practice, framing it as the foundation of his boundary-breaking career. Featuring more than 200 artworks—including rarely seen drawings alongside paintings, sculptures and prints—this exhibition offers an unprecedented opportunity to experience seven decades of his graphic production while shedding light on his constant experimentation with various materials, tools and techniques.
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Test Literary Series

  • Things to do
  • Literary events
  • Logan Square
Test Literary Series
Test Literary Series
Photograph: Jeff Marini
The Whistler’s monthly lit series pops up on the second Wednesday of every month, bringing an evening of readings, workshopping and discussion to the Logan Square cocktail bar. Each show is followed by an installment of the Relax Attack Jazz Series, a free event with a constantly rotating bill.

Family Storybook Yoga

  • Kids
  • Lincoln Park
Family Storybook Yoga
Family Storybook Yoga
Photograph: Shutterstock
Find your flow with the whole family in the cozy confines of the Peggy Notebaert Nature Museum at a Brain to Belly Kids Yoga session! This creative class flows through several fun poses, each one complementing the month's children's story. Children (ages two to eight) and their grown-ups will enjoy moving, breathing and connecting together while bringing the story's plot to life. Bonus: Your ticket includes full access to all museum exhibits, so stick around after class!
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