Chicago · events
Things to do in Chicago, May 2027
Browse 12 upcoming events and things to do in Chicago during May 2027. Highlights include Chicago Cubs vs. Seattle Mariners, Chicago Cubs vs. Seattle Mariners, Chicago Cubs vs. Seattle Mariners and more. Each listing links to tickets, venue details and practical visitor info.
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Peak festival build-up
May tends to be a strong month for festivals across the served markets, with long weekends, open-air concerts and city-wide cultural events picking up pace.
- Browse open-air concerts, food festivals and city-wide cultural events
- Take advantage of the public-holiday long weekends common this month
- Book early for peak-summer festivals that can sell out weeks in advance