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May 2020 events calendar for Chicago

The arrival of May 2020 events in Chicago means summer's just around the corner. Find things to do, festivals and more.

Buckingham Fountain
Photograph: Neal O'Bryan

You've probably spent the better part of the past six months indoors, so the arrival of May (and warm spring weather) is a cause for celebration. It's the time of the year when Chicago rooftop bars open for business and the best outdoor restaurants in Chicago are usually packed with folks soaking up the sun. The rise in temperature is accompanied by lots of May events, including the beginning of summer festival season, with events like Mayfest, Mayfestiversary and the Belmont-Sheffield Music Festival taking over streets throughout the city. The May concert calendar is also packed with great options, including sets from R&B legend Al Green, singer-songwriter Weyes Blood and classic rock heroes the Who. And don't forget about May events like Memorial Day weekend, an exhibition devoted to Hamilton and the arrival of Chicago Craft Beer Week. Fill your spring itinerary with the help of our May events calendar.

RECOMMENDED: Our complete events calendar for Chicago in 2020

Featured events in May 2020

Hamilton: The Exhibition
Illustration: David Korins
Museums, History

“Hamilton: The Exhibition”


Experience the life of Alexander Hamilton at this stand-alone exhibition, created by the team behind the hit musical Hamilton. Debuting in Chicago, "Hamilton: The Exhibition" takes visitors on a journey from a trading post in St. Croix to the New Jersey hilltop where the Founding Father was shot in a duel, using imaginative environments (created by the Broadway production's set designer David Korins) to immerse guests in the historical tale. Hamilton creator Lin-Manuel Miranda serves as the exhibition's narrator (via a high-tech headset), fleshing out details as you make your way through the display and listen to rearranged music from the Broadway show. Highlights of the 20,000-square-foot experience include a moving sculpture representing the hurricane that brought Hamilton to America and a 70-foot parchment map of Manhattan circa 1772 outfitted with scale models of key locations, like Fraunces Tavern and King’s College.

Gallagher Way
Photograph: Courtesy Gallagher Way

Movie Night at Gallagher Way

icon-location-pin Gallagher Way, Wrigleyville

Wrigley Field-adjacent greenspace Gallagher Way teams up with the Music Box Theatre to program free outdoor movie screenings on Wednesday evenings when the Cubs are on the road. Nearly all of the films being shown are family-friendly (with the exception of the R-rated High Fidelity) so feel free to bring along the kids. Gates open for each screening at 6pm and the movies begin at 7:30pm, giving you some time to claim a spot on the lawn and grab food from Big Star, West Town Bakery or the Smoke Daddy food truck. In May, you can catch Wayne's World (May 15) and The Breakfast Club (May 29).

Morton Arboretum Nature Connects
Photograph: Michael Hudson
Art, Outdoor art

“Nature Connects: Art with LEGO Bricks”

icon-location-pin Morton Arboretum, Suburbs

Take in 15 sculptures spread throughout the Morton Arboretum's pathways, including an eight-foot dragonfly, a peacock, a turtle and a nearly life-size family of deer—all made out of LEGO bricks. The intricate models are the work of New York-based artist Sean Kenney, who is well-known for turning the tiny plastic bricks into creative works that tour the world as part of the "Nature Connects" exhibition.

Hallie Duesenberg

Randolph Street Market Festival

icon-location-pin Randolph Street Market, West Loop

More than 100 vendors hawk their antique housewares, furniture, ephemera, clothing and more at this indoor-outdoor festival. Stop in for vintage clothes and jewelry, a vinyl swap meet, a fancy food market and global goods bazaar or bring your own items for appraisal. This event typically occurs on the last weekend of each month. During the warm-weather months of May–September, the market adds an outdoor area, offering even more vintage shopping and a beer garden.

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