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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”

icon-location-pin 1535 S Linn White Dr, Museum Campus

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).

Cirque du Soleil: Volta
Photograph: Matt Beard
Theater, Circuses & magic

Cirque du Soleil: Volta

icon-location-pin Soldier Field South Parking Lot, Near South Side

Cirque du Soleil's latest touring showcase of jaw-dropping physical feats draw inspiration from the world of street sports, incorporating acrobatic BMX bike stunts, breakdancing and rope skipping. The narrative of Volta is centered around a gameshow contestant named Waz, who is thrown into a series of challenges (involving people swinging from the rafters, contorting their bodies and pulling off BMX tricks, no doubt) that allow him to discover his individuality. Featuring colorful costume designed by Zaldy Goco (who has worked with Lady Gaga and RuPaul’s Drag Race) and a pulsing electronic soundtrack, Volta is the kind of multi-sensory experience that Cirque du Soleil excels at—and it all takes place under a big top tent in Soldier Field's South Parking Lot.

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.

Theater and dance in May 2020

Photograph: Sean Williams


icon-location-pin Lookingglass Theatre, Magnificent Mile

The last of this season’s many Frankenstein adaptations, all of which commemorated the novel’s 200th anniversary, this production from writer-director David Catlin (creator of Moby Dick and Lookingglass Alice) captures the night that Mary Shelley first let loose her tale of one man’s triumph over death—and the lonely creature that paid the price.

Photograph: Patrice Lamoureux


icon-location-pin Soldier Field | Chicago, IL, Museum Campus

For the premiere of its new show Volta, Cirque du Soleil plops a big top tent in Soldier Field’s parking lot. It’s a fitting location, as the spectacle draws on the spirit of street sports and features a full-blown BMX park mounted on stage. All of that is in addition to Volta’s original score from M83’s Anthony Gonzalez.

Photograph: Jeff Sciortino


icon-location-pin Chicago Shakespeare Theater, Streeterville

Join all six of King Henry VIII’s wives—Catherine of Aragon, Anne Boleyn, Jane Seymour, Anne of Cleves, Katherine Howard and Catherine Parr—at Chicago Shakes as they push their murderous, conniving husband aside and take back the mic, sharing and singing their own stories in this history lesson turned pop-concert spectacular imported from the U.K.


Queen of the Mist

icon-location-pin The Den Theatre, Wicker Park

In this Chicago premiere from composer Michael John LaChiusa, local legend Barbara E. Robertson stars as Annie Edson Taylor, who in 1901 became the first woman to go over Niagara Falls—in a barrel she designed herself. Firebrand Theatre has been on a roll of late, and this production should be no exception.

GYG Chicago TTD

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