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May 2023 events calendar for Chicago

The arrival of May 2023 events in Chicago means summer's just around the corner. Find things to do, exhibitions and more.

Jeffy Mai
Edited by
Jeffy Mai
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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, whether you want to pay your respects at the parade and wreath-laying ceremony downtown or take a dip at the city's best beaches. So start getting ready for another glorious summer with our May 2023 events calendar for Chicago.

RECOMMENDED: Our complete events calendar for Chicago in 2023

Featured events in May 2023

  • Comedy
  • Uptown

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.

GYG Chicago TTD

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