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May 2023 events calendar for Chicago

The arrival of May 2023 events in Chicago means summer's just around the corner. Find things to do, exhibitions and more.

Jeffy Mai
Edited by
Jeffy Mai

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 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. So start getting ready for another glorious summer with our May 2023 events calendar for Chicago.

RECOMMENDED: Our complete events calendar for Chicago in 2023

Featured events in May 2023

  • Things to do
  • Festivals
  • Loop

This annual festival assembles luminaries from the fields of politics, journalism and the arts for a multi-week series of programming across the city, with events ranging from lectures and discussions to screenings and musical performances. Not sure which events to hit? Some of the fest’s biggest speakers include Hillary Clinton, Rainn Wilson, Andrew Rannells and Andy Cohen. You can see a full schedule of programming on the Chicago Humanities Festival website

  • Shopping
  • Markets and fairs
  • West Loop

Originally established in the late 1800s, the Maxwell Street Market brought vendors, musicians and cooks to an open-air flea market where shoppers could find just about anything they wanted. The market introduced the Maxwell Street Polish sausage, provided a venue for rising Chicago blues musicians and was immortalized in a scene in The Blues Brothers. These days, the market sets up on nearby Desplaines Street (between Roosevelt and Howard) every Sunday, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. Don't let the cold or wet weather scare you away—the Maxwell Street Market takes place outdoors year-round.

  • Movies
  • Wrigleyville

Wrigley Field-adjacent plaza Gallagher Way is once again showing 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 $33—check out the Gallagher Way website for more details. Gates open at 6pm for each screening and the movies start at 7:30pm.

  • May 17: Ferris Bueller's Day Off
  • May 31: E.T. the Extra-Terrestrial
  • June 7: The Mitchells vs. The Machines
  • July 5: Jumanji: Welcome to the Jungle
  • July 12: Clueless
  • July 26: Top Gun: Maverick
  • August 23: Puss in Boots: The Last Wish
  • August 30: The Dark Knight
  • September 13: Back to the Future
  • September 27: The Blues Brothers
  • Things to do
  • Fireworks
  • 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.

  • Art
  • Film and video

Projecting a 25-story-tall video installation on the side of the Merchandise Mart, ART on THE Mart's 2023 programming kicks off with a new piece by internationally-renowned artist Derrick Adams“Funtime Unicorn: Ruby Rides Through Four Seasons”which will be on display from April 14 to July 5. The spring season will also feature artwork from soon-to-graduate Chicago Public School students, officially titled “Select Works from the CPS Class of 2023.” ART on THE MART's array of 34 digital projectors show the creations at 8:30pm and 9pm every evening. It’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

  • Music
  • Jazz
  • Greater Grand Crossing

The South Side Jazz Coalition is hosting a series of free monthly jazz performances this summer on the steps of the St. Columbanus Catholic Church in Greater Grand Crossing. Bring a lawn chair, some snacks and prepare to hear some top-notch music from the Chicago jazz community—plus, every performance ends with a jam session. 

  • Restaurants
  • Loop

Looking for a one-of-a-kind dinner? Then head to Fairmont Chicago, where the hotel has partnered with TableMation Studios to bring Le Petit Chef: An Immersive Dining Experience to town. The unique culinary journey pairs a five-course meal with virtual reality theater. Guests will follow an animated chef as he guides them through a multisensory tasting menu—with the help of 3D projection mapping—and tells a story of the history, ingredients and techniques used to make each dish.

  • Things to do
  • Exhibitions
  • Streeterville

Yer a wizard, Harry! Or at least, you can pretend to be one at this immersive Harry Potter experience that’s popping up at Water Tower Place through September 2023. Visitors are invited to step into Harry’s life at Hogwarts with interactive features like Quidditch lessons, Charms and Defense Against the Dark Arts classes, sipping sweet drinks at the Butterbeer Bar, Patronus-seeking in the Forbidden Forest and learning their Hogwarts house via the Sorting Hat, among other magical experiences. FYI: In addition to regular operating hours, the exhibition is open on “select” Mondays, Tuesdays and Wednesdays and may offer different hours around holidays. 

  • Museums
  • Science and technology
  • Hyde Park

Tap into feelings of childhood nostalgia at the Museum of Science and Industry’s newest exhibit, a colorful glimpse into the world of Mold-A-Rama™ machines. Explore a collection of popular, rare and experimental souvenirs, learn about the history of the machines’ production and breathe in the iconic scent of their plastic toymaking—you can even take home a few new Mold-A-Rama™ souvenirs if you’re looking to expand your collection. 

  • Museums
  • Special interest
  • Logan Square

Chicago Gamespace, a video game museum in Logan Square, is opening a new exhibition dedicated to the game universe of TRON. Visitors will enter through Flynn's Arcade, the immortal arcade owned by Jeff Bridges' Flynn character in the sci-fi classic, and learn about the original TRON arcade game’s history and development before entering an immersive Light Cycle arena featuring other games from the franchise. General admission is $8 for adults and $5 for kids, and includes access to the video game history collection.

GYG Chicago TTD

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