May is a jam-packed month in Chicago — summer is on the horizon, tulips are blooming all over the city, and weekends fill up with endless food, drink, cultural, and musical events. From the start of festival season to spring flower shows to major art fairs and cultural celebrations, there’s no shortage of fun to be had in the city this month.
Check out these top picks for things to do in Chicago throughout the month of May, including theatre and film festivals, Memorial Day weekend events, AAPI Heritage Month events, and more.
Top events in Chicago this May
Chicago Cabaret Week (May 9 – 18): Enjoy discounted tickets to a range of cabaret performances across Chicago, including blues, Broadway, burlesque, jazz, R&B, and more in intimate venues.
Pullman Railroad Days (May 17 – 18): A spring favorite event returns to the Pullman neighborhood, where families and locals can explore restored railcars from Pullman’s heyday.
Renegade Craft Fair (May 17 – 18): Over 200 local artists and vendors will showcase their works of art, jewelry, design, crafts, and more at Andersonville’s Renegade Craft Fair.
Marvel’s Spider-Man: The Exhibit (Opens May 22): Superfans of Spider-Man won’t want to miss the newest immersive exhibit at the Museum of Science & Industry.
Belmont Sheffield Music Festival (May 23 – 25): This year is the 40th edition of this Lakeview music festival, featuring a weekend full of tribute bands, artisan shopping, food, drink, and more.
Navy Pier summer fireworks (starting May 24): Kick off the summer season with these spectacular fireworks, which will light up Chicago’s lakefront twice a week all summer long.
Chicago Memorial Day Parade (May 24): The long weekend in Chicago is always marked by a downtown parade and wreath-laying ceremony at Daley Plaza.
Randolph Street Market (May 24 – 25): One of Chicago’s biggest street markets returns to the West Loop with thousands of vendors selling antique goods, art, vinyl, jewelry, and so much more.
Sueños Music Festival (May 24 – 25): Head to Grant Park for a two-day Latin music festival that features a variety of Reggaeton and Latin performers, plus art, activities, a Ferris wheel, and more.
Maifest (May 29 – June 1): Lincoln Square’s annual German celebration returns, bringing traditional food, drink, and German music all weekend long.
Do Division Street Festival (May 30 – June 1): The annual West Town fest is back in full swing this year, showcasing plenty of live music, a fashion show, family fun, and so much more.
More events in Chicago this May
Chicago Critics Film Festival (May 2 – 8): The Music Box Theatre in Lakeview will be home to this year’s Critics Film Festival, curated by film critics and showcasing over 25 films across genres.
Mexico Fest at Navy Pier (May 2 – 4): Head to Navy Pier for a free celebration of Mexican culture, bringing together music and dance performances, workshops, and over 30 vendors.
Chicago Fire at Soldier Field (May 3 and 10): Feel the thrill of live soccer as the Chicago Fire takes the field at their home stadium on the lakefront.
Andersonville Wine Walk (May 4): What better way to explore the Northside neighborhood than with sips of wine along the way? The annual Andersonville wine walk showcases two different routes, highlighting multiple restaurants and wine bars for tastings.
Hadestown at the CIBC Theatre (May 6 –18): The CIBC Theatre will be home to a limited run of Hadestown, the Tony Award-winning musical that reimagines the Greek myth story of Orpheus and Eurydice.
Beer Under Glass (May 9): As a kick-off to Illinois Craft Beer Week, over 80 breweries will come together on the rooftop terrace of the Harris Theater for a sampling event showcasing over 200 pours.
SAUCED Market (May 9 – 10): Half Acre Beer Co. will host this year’s SAUCED spring night market, showcasing over 45 vendors and their artisanal goods. Enjoy small bites, drinks, and live music as you browse.
Spring Wine Tasting at Morton Arboretum (May 10): Sip and sample a wide variety of wine while savoring the outdoor beauty of the Arboretum’s Meadow Lake Trail.
Switch on Summer (May 10): Enjoy the spectacle of the iconic Buckingham Fountain being officially turned on for the season, alongside live music, dance, and cultural performances.
Sapphopalooza at the Music Box Theatre (May 10 – June 1): This film festival puts a spotlight on sapphic films, from groundbreaking classics to cult favorites.
Adults Only at Lincoln Park Zoo (May 10): Leave the kids at home for a special adults-only night at the zoo, featuring after-hours viewing of the animal habitats, pop-up bars, live music, karaoke, lawn games, and more.
Beyoncé at Soldier Field (May 15, 17 – 18): Get your cowboy gear ready as Beyoncé and her Cowboy Carter tour comes to Soldier Field for a three-night event.
Attend the Asian American Film Showcase (May 16 – 22): This 28th annual film showcase provides a platform for new works by established and emerging Asian American filmmakers at the Gene Siskel Film Center.
Lincoln Park Mayfest (May 16 – 18): Enjoy live local music, neighborhood food and drink, and a look at the Spring Fine Art Mart, which showcases local and national art from fine artists.
Chicago Cubs vs. Chicago White Sox (May 16 – 18): These hometown rivals will face off during this year’s highly anticipated Crosstown Classic, hosted at historic Wrigley Field.
Lincoln Roscoe Art & Craft Fair (May 17 – 18): The family-friendly art fest returns to the Lakeview neighborhood, bringing work from over 75 artists, a live painting class, a face painting tent, and a special kids’ art zone.
Wright Plus Architectural Housewalk (May 17): Architecture lovers won’t want to miss this unique opportunity to tour the exteriors and interiors of original Frank Lloyd Wright houses throughout Oak Park.
Hiplet Ballerinas at The Auditorium (May 17): Come marvel at this unique fusion of classic pointe, hip-hop, and other dance styles inside the stunning Auditorium Theatre.
Millennium Park Summer Workouts (May 17, 24, and 31): Grab your workout mat and head to Millennium Park for a free fitness class, featuring pilates, yoga, kickboxing, and more.
Maxwell Street Market (May 18): Head to this historic market to shop handmade crafts, clothing, housewares, and more. Street food vendors will also be offering “Maxwell Street” original items with origins tied to the neighborhood.
Post Malone at Wrigley Field (May 22): Post Malone comes to Wrigley Field for the first time, featuring a jam-packed night of performances alongside Jelly Roll, Sierra Ferrell, and Chandler Walters.
ART on THE MART (through May): This nightly art and light installation is back with new original works displayed across two city blocks each night along the Chicago River.
Spirited Sound Making at Hyde Park Art Center (May 22): This experimental performance uses reconstructed instruments to reimagine the rhythms of healing musical ceremonies.
Mayfestiversary (May 24 – 25): Two beloved local breweries, Begyle Brewing and Dovetail Brewing, come together for this annual celebration with live music, food, and, of course, beer.
Windy City Hot Dog Fest (May 30 – 31): Celebrate one of Chicago’s most iconic bites at this annual festival in Portage Park, which will award the city’s best hot dog.
Chicago Farmers Markets (through May): Shop locally grown produce, artisanal goods, ready-to-eat foods, and more at neighborhood farmers markets throughout the city.
Frida Kahlo’s Month in Paris (through May): Catch this exciting new exhibit at the Art Institute of Chicago, highlighting the works of Frida Kahlo during her month-long stay in Europe.
Candlelight Concerts (through May): A string quartet performs in unique venues, highlighting the music of Queen, Adele, ABBA, Taylor Swift, and many more.
Go Dog Go VE PERRO ¡VE! (through May): The Chicago Children’s Theater has brought to life the beloved children’s story Go Dog Go in a bilingual performance that blends English and Spanish.
The Jury Experience (through May): The Chopin Theatre in West Town invites guests to an immersive theatrical event where the audience is the jury that examines evidence and reaches a verdict.
Chicago Humanities Festival (through May): The spring celebration brings iconic names to Chicago for stimulating conversations, including actor Ed Helms, cookbook author Melissa Clark, activist Amanda Nguyen, and so many more.
Adler at Night (through May): Every Wednesday evening, head to the Adler Planetarium for special late-night hours and free admission for Illinois residents.
