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HappeninsChicagoMay

Things to do in Chicago in May 2027

The Polish Constitution Day Parade, held since 1891, goes up Columbus Drive on the first Saturday of May, and for one Saturday the owners of Wright-designed houses in Oak Park let ticket holders inside. Anime Central and Skokie Festival of Cultures land in May, with 6 more on the list below.

Follow Chicago in your calendar: Google CalendarApple or Outlook Confirmed dates only. New ones appear on their own.

Starting in May

Anime Central Conventions & Expos

Anime Central

Friday, May 14 to Sunday, May 16 Donald E. Stephens Convention Center, Rosemont
Ticketed

Expected in May, dates not announced yet

Wright Plus Housewalk Arts & Culture

Wright Plus Housewalk

Expected May 2027 Frank Lloyd Wright Home and Studio, Oak Park
Ticketed
Chicago Memorial Day Parade Holidays & Parades

Chicago Memorial Day Parade

Expected May 2027 Daley Plaza (wreath laying) and Dearborn Street (parade), Chicago
Ticketed

Already on when May starts

These started in an earlier month and are still running.

Doc10 Film Festival Arts & Culture
Running through May 2

Doc10 Film Festival

Friday, Apr 23 to Sunday, May 2 The Davis Theater and Gene Siskel Film Center, Chicago
Ticketed
C2E2 Conventions & Expos
Running through May 2

C2E2

Friday, Apr 30 to Sunday, May 2 McCormick Place (South Building), Chicago
Ticketed

5 more run every week in Chicago year round, including Green City Market and Randolph Street Market. See the full calendar.

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