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Things to Do in Chicago — May 2027
Explore 55 upcoming things to do in Chicago in May 2027, including TBD/TBD and Ordinary Days. Compare dates, locations and practical details to plan your day.
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Chicago events today & tonightWhat is still happening today →Chicago events this weekendSaturday, Sunday and weekend plans →Chicago events this monthBrowse the current event calendar →Concerts in ChicagoLive music, artists and tour dates →Comedy shows in ChicagoStand-up, clubs and live comedy →Sports in ChicagoGames, matchups and tickets →Shows in ChicagoTheatre, plays and musicals →Free events in ChicagoPlans marked free when available →
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55 things to do
Showing 25–48 of 55 · Chicago
Fri, May 14, 2027Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Experience
Sat, May 15, 2027Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Experience
Sun, May 16, 2027Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Experience
Fri, May 21, 2027Time TBA
Sports · Chicago
Chicago Cubs vs. Washington Nationals
Check ticketsChicago Cubs
Fri, May 21, 2027Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Experience
Sat, May 22, 2027Time TBA
Sports · Chicago
Chicago Cubs vs. Washington Nationals
Check ticketsChicago Cubs
Sat, May 22, 2027Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Experience
Sun, May 23, 2027Time TBA
Sports · Chicago
Chicago Cubs vs. Washington Nationals
Check ticketsChicago Cubs
Sun, May 23, 2027Time TBA
Theatre & Show · Chicago
The Chicago Theatre Tour Experience
Check ticketsThe Chicago Theatre Experience
Tue, May 25, 2027Time TBA
Sports · Chicago
Chicago Cubs vs. Kansas City Royals
Check ticketsChicago Cubs
Wed, May 26, 2027Time TBA
Sports · Chicago
Chicago Cubs vs. Kansas City Royals
Check ticketsChicago Cubs
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Explore 55 upcoming things to do in Chicago in May 2027, including TBD/TBD and Ordinary Days. Compare dates, locations and practical details to plan your day.
If your schedule is flexible in Chicago, try different dates and nearby venues to uncover more things to do.
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If Kingston Mines - Chicago Blues Center and Citadel Theatre Lake Forest are on your shortlist, compare their locations and travel time before choosing a date.
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