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Shutterstock | A sunny Chicago day by the river
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The best May 2026 events in Chicago

Make the most of spring with our guide to the best things to do in Chicago this month.

Christina Izzo
Edited by Christina Izzo
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Once May rolls around, we know summer in Chicago is just around the corner. Need evidence? Look no further than the slate of summer festivals coming up this month—including returning favorites like Mole de Mexico in Pilsen and Sueños Music Festival in Grant Park—or the throngs of people hanging out at Chicago rooftop bars and outdoor restaurants every weekend. Plus, don't forget to plan out holidays like Mother's Day (we bet your mom would love brunch reservations) and Memorial Day weekend in Chicago this month. So enjoy spring to the fullest and start getting ready for another glorious summer with our May 2026 events calendar for Chicago.

RECOMMENDED: Events calendar for Chicago in 2026

Time Out Market Chicago

The best events in Chicago this May

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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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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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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David Byrne's Theater of the Mind

  • Things to do
  • Exhibitions
  • River North
David Byrne's Theater of the Mind
David Byrne's Theater of the Mind
Photograph: Matthew DeFeo, Courtesy of the Silverman Group
Talking Heads frontman, Broadway innovator and all-around creative polymath David Byrne is once again blurring the line between art and science, this time in the middle of downtown Chicago. “Theater of the Mind” is Byrne’s latest experiment in perception, identity and theatrical immersion—and it’s happening inside a real office space. Created with writer and philanthropist Mala Gaonkar, the 15,000-square-foot experience invites audiences of just 16 at a time to explore a series of rooms designed to mess with your senses and make you question, well, yourself.

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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