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Aerial view of Oak Street Beach, Chicago
Photograph: Shutterstock

May 2022 events calendar for Chicago

The arrival of May 2022 events in Chicago means summer's just around the corner. Find things to do, exhibitions and more.

Emma Krupp
Edited by
Emma Krupp
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Once May rolls around, we know summer in Chicago is just around the corner. Need evidence? Look no further than the slate of summer festivals coming up this month—including returning favorites like Mole de Mexico in Pilsen and newcomers like the inaugural Sueños Music Festival in Grant Park—or the throngs of people hanging out at Chicago rooftop bars and outdoor restaurants every weekend. Plus, don't forget to plan out holidays like Mother's Day (we bet your mom would love brunch reservations) and Memorial Day weekend in Chicago this month, whether you want to pay your respects at the parade and wreath-laying ceremony downtown or take a dip at the city's best beaches. Start getting ready for another glorious summer with our May 2022 events calendar for Chicago.

RECOMMENDED: Our complete events calendar for Chicago in 2022

Featured events in May 2022

  • Music
  • Music festivals
  • price 3 of 4
  • Millennium Park
Chicago's Rudio Fest has done a great job of bringing Latin rock acts to the city, but there's never been a summer festival devoted to reggaeton... until now. The teams behind Mexico's Baja Beach Fest and Lollapalooza are joining forces to present the first Sueños Music Festival, a two-day Memorial Day weekend fest that brings 20 Latin performers to Grant Park. Taking place on a single stage in Grant Park's Hutchinson Field, Sueños will feature headlining sets from Colombian rapper J Balvin, Puerto Rican singer Ozuna and veteran reggaeton duo Wisin y Yandel. Other notable names on the lineup include rapper Myke Towers, Dominican hip-hop act El Alfa and Mexican-American quartet Fuerza Regida. In addition to two days of music, organizers are promising food from some of Chicago best Latin restaurants, aftershows at local music venues, custom art installations and a Ferris wheel in the park that you can ride between (or during) sets. It's one of the largest new festivals to come to launch in Chicago in years and a fitting addition to a summer festival calendar that's likely to be more crowded than ever.
  • Things to do
  • Fireworks
  • price 0 of 4
  • Streeterville
During the summer, one of the best aerial displays you'll find in Chicago originates from Navy Pier. The Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays and Saturdays) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. Of course, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.
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  • Time Out Market
  • West Loop
Every Sunday from 11am to 3pm, Time Out Market Chicago's chefs offer a variety of delicious brunch dishes, from Hangover Ramen with shrimp and smoked pork to a stack of Buttermilk Pancakes layered with whipped mascarpone. Order as much as you want, grab a mimosa pitcher from the bar and stick around from 1 to 3pm for a set of tunes from the Chicago Soul Jazz Collective. 
  • Things to do
  • Festivals
  • price 0 of 4
  • Lower West Side
Pilsen's annual Mole de Mayo street festival—which honors the traditional Mexican sauce with a mole cook-off, plus a market full of vendors—returns to the neighborhood over Memorial Day weekend for its first in-person celebration since 2019. Grab some enchiladas smothered in aromatic mole and don't miss the festival's lucha libra wrestling matches. 
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  • Things to do
  • Festivals
  • price 1 of 4
  • Lake View
Love cover bands? Head to Lakeview (right by the Belmont Red Line station) for three days of music, featuring local tribute acts like Don't Speak, Fletcher Rockewell and Rod Tuffcurls & the Bench Press. A second stage hosts an eclectic array of community performers, including folks from the Japanese Cultural Center and local DJs accompanied by drag performers like Lucy Stoole, DJ Ca$hera, Irregular Girl and Tenderoni. Plus, you'll find beer, wine and plenty of area vendors to browse while you hang out on the street.
  • Art
  • Film and video
  • price 0 of 4
Projecting a 25-story-tall video installation on the side of the Merchandise Mart, Art on theMart's spring program focuses on two climate change-themed projections presented in partnership with the Shedd Aquarium. The first, Floe, was created by Chicago choreographer Carrie Hanson (in collaboration with her dance company, The Seldoms) and spotlights climate change through melting ice, extreme weather and the human body, set to soundscapes of icebergs, water and rain. The second, Choral, is by the collaborative localStyle and depicts the human impact on coral ecosystems. Art on theMART's array of 34 digital projectors display the 30-minute program at 8:30 and 9pm every evening. The show is best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.
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Memorial Day Parade
  • Things to do
  • price 0 of 4
  • Loop
After a wreath is laid at the eternal flame in Daley Plaza at 11am in remembrance of those who died serving in the U.S. armed services, Chicago's annual Memorial Day Parade marches down State Street (from Lake to Van Buren streets) beginning at noon. Crowds line the street waving flags and paying their respects as part of this Chicago tradition, which dates all the way back to 1870.
  • Comedy
  • price 0 of 4
  • Uptown
This weekly “live magazine” is a cavalcade of culture, politics and wit featuring journalists, actors, comedians and musicians offering idiosyncratic reports on the news of the day. Head to Uptown’s iconic Green Mill for drinks, hot takes and laughs; the longstanding Saturday afternoon edition tends to run about two and a half hours.
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  • Art
  • Painting
  • Grant Park
The Art Institute of Chicago has teamed up with London's Tate Modern to mount the first major retrospective of Paul Cezanne's work in more than 25 years, exploring the Impressionist painter's legacy across a variety of mediums and genres. Visitors can explore some of Cezanne's most enduringly iconic works—including his lush still life paintings and landscapes—as well as rarely-seen compositions pulled from private collections, encompassing a total of 90 oil paintings, 40 watercolors and drawings and two complete sketchbooks. You'll need an additional ticket to gain access to the exhibit, but you'll rarely find such a comprehensive perspective on this seminal artist's life and work. 
  • Movies
  • price 0 of 4
  • Wrigleyville
Wrigley Field-adjacent plaza Gallagher Way is once again teaming up with the Music Box Theatre to program free outdoor movie screenings this summer. Admission is free and attendees are welcome to bring their own food, enjoy on-site concessions or snag a meal from nearby restaurants like Big Star and Smoke Daddy. VIP seating is also available for $30—check out the Gallagher Way website for more details. Gates open at 6pm for each screening and the movie starts at 7:30pm May 11: Bill and Ted's Excellent AdventureMay 25: RocketmanJune 8: Mamma Mia!June 22: Josie and the PussycatsJuly 6: Dirty DancingJuly 20: School of RockJuly 27: Pitch PerfectAugust 3: GreaseAugust 17: EncantoAugust 31: Almost FamousSeptember 14: SelenaSeptember 21: Bohemian Rhapsody

GYG Chicago TTD

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