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May 4, 2026

Your Guide to May 2026 in Chicago

City Cast Chicago

Your Guide to May 2026 in Chicago

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May flowers are blooming all around us as summertime Chicago is on the horizon. We’ve got your guide to what’s happening in Chicago this month — rain or shine. Host Jacoby Cochran, creative producer Michelle Navarro, and audience development manager Chima Ikoro have events to look forward to, tips for May, and news stories to watch.


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