May is a jam-packed month in Chicago — summer is on the horizon, tulips are blooming all over the city, and weekends fill up with endless food, drink, cultural, and musical events. From the start of festival season to spring flower shows to major art fairs and cultural celebrations, there’s no shortage of fun to be had in the city this month.
Check out these top picks for things to do in Chicago throughout the month of May, including theatre and film festivals, Memorial Day weekend events, Cinco de Mayo festivities, AAPI Heritage Month events, and more.
Top events in Chicago this May
Suenos Music Festival
Celebrate Mexican culture at Navy Pier (May 3 – 5): Head to Navy Pier for a free celebration of Mexican culture, bringing together music and dance performances, workshops, and over 30 vendors.
Take a tour of the historic Pullman neighborhood (May 5): Walk through history on this guided tour of the Pullman National Historical Park and surrounding area.
Attend the Asian American Film Showcase (May 17 – 23): This 27th annual film showcase provides a platform for new works by established and emerging Asian American filmmakers at the Gene Siskel Film Center.
Try a variety of cuisines during AAPI Restaurant Week (May 17 – 26): Discover a multitude of AAPI-owned restaurants across the city and suburbs, all offering special deals and discounts throughout the week.
Feast on Mexican cuisine at Mole de Mayo (May 24 – 26): Pilsen will be home to its annual outdoor mole cook-off, featuring an open-air mercado with local shops, music, dancing, and more.
Navy Pier fireworks
See fringe theatre at Rhino Festival (Starting May 25): This year is the 35th annual Rhinoceros Theater Festival, Chicago’s longest-running fringe theater festival, when 50 artists showcase their plays, music, and art throughout six venues across the city.
Feel the beat at Suenos Music Festival (May 25 – 26): Head to Grant Park for a two-day Latin music festival that features a variety of Reggaeton and Latin performers, as well as art, activities, a Ferris wheel, and more.
Be dazzled by the Navy Pier fireworks (starts May 25): Kick off the summer with the first fireworks display of the season at Navy Pier over Memorial Day weekend.
Get involved!
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