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 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 2027 events calendar for Chicago.
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