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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

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.

GYG Chicago TTD

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