The best May 2026 events in Chicago

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.

Whether you’re parenting a pint-sized Pokémon devotee or a nostalgic millennial still clinging to a holographic Charizard card for its “possible resale value” (guilty), the Pokémon Fossil Museum is designed to surprise and delight. Making its U.S. debut at the Field Museum in spring 2026, the international exhibition invites visitors to compare Fossil Pokémon like Tyrantrum and Archeops with real-world fossils—including SUE the T. rex. Expect Pokémon models, real fossil excavation tools and immersive soundscapes throughout.

During the summer, the Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across the pier's public spaces. During the winter months, the pyrotechnics return for a much-needed encore. If you're feeling weary of crowds, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

Displaying a 25-story-tall video installation on the side of THE MART, ART on THE MART is the largest permanent digital art projection in the world, with programming that changes seasonally. ART on THE MART's array of 34 digital projectors show the creations after dusk every evening. Running Thursdays through Saturdays beginning at 7:30pm, it’s best viewed from the section of the Chicago Riverwalk between Wells Street and Franklin Street.

Talking Heads frontman, Broadway innovator and all-around creative polymath David Byrne is once again blurring the line between art and science, this time in the middle of downtown Chicago. “Theater of the Mind” is Byrne’s latest experiment in perception, identity and theatrical immersion—and it’s happening inside a real office space. Created with writer and philanthropist Mala Gaonkar, the 15,000-square-foot experience invites audiences of just 16 at a time to explore a series of rooms designed to mess with your senses and make you question, well, yourself.

How are some of the most iconic costumes of the past century made? Costume designer Paul Tazewell pulls back the curtain in this behind-the-scenes exhibition. Highlights include costumes from Wicked, Janelle Monáe’s MET Gala looks and Steven Spielberg’s West Side Story. Sketches, videos and narration reveal how imagination becomes wearable art.

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 Maxwell Street, between South Halsted Street and South Union Avenue on Sundays, where visitors will find vendors hawking their wares, an abundance of delicious Mexican food and occasional performances by local bands and dance troupes. 

Spin classes and weight lifting can wait for the winter. This summer, jump start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn and in Wrigley Square every Saturday from May through August.

Immerse yourself in a new perspective on legendary artist Henri Matisse at this exciting new exhibition at The Art Institute of Chicago. Bedridden and unable to paint in the 1940s, Matisse turned to a new, more accessible medium: cut paper. Mining his memories of circuses, world travels, folktales and concerts in Parisian music halls, he produced a series of 20 maquettes that will be on display for the public to enjoy.

Discover one-of-a-kind treasures from over 100 local small businesses at this curated indoor marketplace. You’ll be able to check out the best in Chicago food, fashion, home goods and art, as well as chat with vendors to learn about how the products are made. Well-behaved dogs are welcome to join the fun, and tickets are discounted when purchased in advance.