We can’t help but love May. The city’s parks are finally bursting with colorful blooms. Tulips begin to line Michigan Avenue, summer events are on the horizon, and the Riverwalk restaurants are remerging after a dreary winter—there’s an unmistakable energy in the air.
Here are our top recommendations for the best things to do in Chicago this May.
A free weekend celebration of Mexican culture at Navy Pier.
Mexico Fest at Navy Pier is a free weekend celebration of Mexican culture featuring live bands and DJs, ballet and folk dancing, mariachi groups, a traditional art market, cultural workshops, and plenty of food.
Swan boats and Surrey bikes return to Humboldt Park on April 25, 2026.
Wheel Fun Rentals is relaunching a fleet of 15 swan boats at the Humboldt Park lagoon boathouse starting April 25, 2026, and will also offer Surrey bike rentals. Pricing is $30 per hour for a swan boat, $29 for a four-wheeled Surrey bike, and $39 for a double Surrey bike.
Smirnoff Ice Smash is celebrating the launch of a new Smash flavor (Strawberry Passionfruit) in a big way – with a FREE party this week! Get a sneak preview of a Two Friends set ahead of Big Bootie Land as well as plenty of drink samplings, food, and epic vibes. Plus, there’s a chance to win your way to Big Bootie Land for free! You in? We thought so. Here are some more details on this secret pop-up party – attendance is not as simple as you might think.
DRINK RESPONSIBLY. DON’T SHARE WITH PEOPLE UNDER 21.
SMIRNOFF ICE SMASH, Premium Flavored Malt Beverage. The Smirnoff Co., New York, NY.
Six Flags Great America reopens on April 25, 2026!
Six Flags Great America in Gurnee will open for the 2026 season on Saturday, April 25, 2026. The park is also marking its 50th anniversary with summer-long celebrations and special experiences.
Visit Tacombi on Cinco de Mayo
After a temporary closure for structural work, Tacombi will reopen on May 5th, and to celebrate, the company will donate 100% of its proceeds to the Tacombi Foundation, its nonprofit organization, to fund a new educational facility in a rural community in Jalisco, Mexico.
The Logan Square Farmers Market debuts at its new permanent Milwaukee Plaza location on May 10.
The Logan Square Farmers Market is moving to a permanent home at the revamped Milwaukee Plaza and a stretch of Logan Boulevard, opening Sunday, May 10, 2026, and will host 103 rotating vendors with 44 farmers each week.
Celebrate 30 years of Pokémon with Excavator Pikachu and real fossils at the Field Museum.
The Pokémon Fossil Museum is a limited-run interactive exhibition at Chicago’s Field Museum that pairs Fossil Pokémon with real-world fossils, features Excavator Pikachu, and includes hands-on tools and exhibits led by museum scientists. The show opens May 22, 2026, and runs through April 11, 2027, with tickets currently available.
Kick off summer at Lincoln Park Mayfest with music, art, and local vendors.
A neighborhood street festival in Lincoln Park featuring live music from local bands, drinks, an art show, and local vendors. It celebrates the start of summer with a relaxed, family-friendly vibe.
Step into a world of wonder at the Wondra immersive art experience.
The Wondra experience is an interactive, immersive art exhibit at Woodfield Mall in Schaumburg, offering sensory installations with lights, sound, and hands-on displays for visitors. The exhibit promises an unforgettable, family-friendly adventure.
Get tickets now for Lupe Fiasco’s post-match show on May 23.
Chicago Fire FC will host Chicago-born LUPE FIASCO as part of its 2026 summer concert series with a post-match showcase on Saturday, May 23, 2026. Tickets for the match and concert are on sale now through the club.
Experience some unforgettable performances in Chicago’s most exquisite venues.
The Candlelight series presents classical and contemporary musicians performing in atmospheric, candlelit venues across Chicago; events take place at various locations throughout the city.
Experience millions of tulips and Dutch heritage at Holland’s Tulip Time this May.
Holland, Michigan’s Tulip Time Festival celebrates Dutch heritage with millions of tulips, parades, marching bands, dancers, fireworks, and both local and national entertainment; the 2026 festival runs until May 9th