May is a jam-packed month in Chicago — spring has arrived in the city, flowers are blooming everywhere from Michigan Avenue to Jackson Park, and weekends fill up with endless food, drink, cultural, and musical events. From the start of festival season to Memorial Day weekend 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. Please note that all events are subject to change.
Top events this May
Chicago Friday Night Flights: Cheers to the city’s award-winning craft beer scene with this tasting event outside Wrigley Field, featuring 36 breweries from across the city.
Spring Flower Show at Garfield Park Conservatory (through May 8): Stroll through spring blooms at the newest flower show taking over the scenic Garfield Park Conservatory.
Pullman Railroad Days (May 14 – 15): This historic neighborhood is hosting a celebration of railroad innovation, featuring train cars from different eras.
Sueños Festival in Grant Park(May 28 – 29): Head to Grant Park for a two-day long Latin music festival that features 15+ reggaeton and Latin performers.
Mole de Mayo in Pilsen(May 27 – 29): Pilsen will be home to its annual outdoor, mole-style cookoff, also featuring an open-air mercado with local shops, music, dancing, and more.
Summer fireworks at Navy Pier(May 28): Start summer on a spectacular note with the first lakefront fireworks show of the season at Navy Pier.
Belmont Sheffield Music Fest(May 28 – 29): For the 36th year, multiple bands will take the stage for a weekend festival in Lakeview filled with music, food, drink, and more.
Immersive Frida Kahlo (through May): Journey through the life of this celebrated Mexican artist with over 500,000 cubic feet of art, 90 million pixels, 1 million frames of video, and more for a true immersive experience.
ART on theMART’s spring program(through May): The world’s largest digital art display returns with two new shows projected on the facade of theMART each evening.
ChiTown Movies (through May): Pull up to this old-school drive-in movie experience in Pilsen to enjoy screenings of popular movies and family-friendly classics.
More things to do this month
One of a Kind Spring Show (April 29 – May 1): Head to theMART for this unique event that showcases the Chicago creative community and more than 300 talented artisans.
Spring/summer exhibits at Wrightwood 659 (opens May 6): This intimate Lincoln Park space is showcasing three new exhibits that explore architecture, Japanese painting, and social engagement through food and art.
Spring Wine Tasting at Morton Arboretum (May 7): Sip and savor more than 80 different wines in a scenic outdoor setting, with booths scattered throughout the Arboretum.
Jazz Brunch at Time Out Market(May 8): The Chicago Soul Jazz Collective takes over Time Out Market for a special Mother’s Day brunch.
Rise Up: Stonewall and the LGBTQ Rights Movement (through May 8): The Illinois Holocaust Museum exhibit covers the Stonewall Uprising, plus connections to Chicago and celebrations of LGBTQ+ pride in Chicagoland.
Relentless at Goodman Theatre (Through May 8): Tyla Abercrumbie’s world premiere play tells the story of a family and their secrets set in 1919 Black Victorian era.
Chicago Mahogany Tours (various dates): Learn more about neighborhoods like Pullman and Bronzeville from Chicago’s favorite urban historian.
The Queen’s Ball: A Bridgerton Experience(through May): Experience 1813 London with an interactive Bridgerton-style evening, complete with music, acrobatic dance performances, and more.
Chef Kwame Onwuachi: Recipes From a Young Black Chef(May 7): Top Chef contender and James Beard award-winning chef, Kwame Onwuachi will be highlighting his new cookbook, My America: Recipes from a Young Black Chef at UIC.
Night Run at Soldier Field(May 7): Part 5K run, and part music fest, the Night Nation Run includes live DJs, light shows, bubble zones, and more at Soldier Field.
American Writer’s Festival (May 15): This free literary festival takes over the Chicago Cultural Center showcasing over 75 contemporary authors, artists, and playwrights.
Human+Nature at Morton Arboretum (through May): The sprawling Arboretum is dotted with stunning large-scale sculptures honoring nature.
Sunday Service at Stony Island Arts Bank (May 15): Resident DJ Duane Powell will host a special edition of Sunday Service, with a dance party celebrating Stevie Wonder.
Chicago Cubs home games (various dates): Usher in the start of summer with a Cubs game at historic Wrigley Field.
Chicago White Sox home games (various dates): Head to Guaranteed Rate to root for the White Sox with pre-game tailgating and in-game fireworks.
Jazz Festival at Palmer Park (May 13): In the Roseland neighborhood, Palmer Park will host live performances by young local jazz artists, plus vendors, art activities, and food trucks.
Chicago Fire at Soldier Field (May 14): Chicago’s professional soccer team faces off against Cincinnati at iconic Soldier Field during this month’s home game.
Chicago boat cruises (through May): Chicago’s lake and river boats are back in action, from architecture tours to scenic dinner cruises.
AAPI Restaurant Week (May 13 – 22): Sample a variety of Asian and Hawaiian cuisines throughout the Chicago area and take advantage of deals and specials at AAPI-owned restaurants.
Switch on Summer at Buckingham Fountain (May 14): Kick off summer at Grant Park, with the official turning on of Chicago’s iconic Buckingham Fountain.
Andersonville Wine Walk(May 15): What better way to explore Andersonville than with sips of wine along the way? The annual Andersonville wine walk showcases multiple restaurants and wine bars with tastings.
Free Family Day at Chicago Children’s Museum (May 19): Enjoy free admission to Navy Pier’s kid-friendly museum, plus live music, crafts, interactive mosaic making, and an add-on street-art mural.
Chicago Humanities Festival (various dates): The spring edition of this thought-provoking conversation series features Anita Hill, Selma Blair, Sarah Cooper, and more.
Lincoln Roscoe Art + Craft Festival(May 21 – 22): Head to Roscoe Village for a weekend festival that includes paintings and sculptures for sale, jewelry, a furniture donation, and plenty of family-friendly fun.
Hyde Park Art & Centered: A Wellness Day (May 21): Hyde Park Art Center hosts this free day of wellness activities, including therapeutic arts, sound meditation, yoga, and more.
Jazzin’ On the Steps (May 22): The South Side Jazz Coalition kicks off its summer series with a return to free jazz on the steps of St. Columbanus Catholic Church.
Jurassic Ocean: Monsters of the Deep at Field Museum(through May): This new exhibit highlights prehistoric marine reptiles, crocodiles, and sharks.
SIX the Musical at the CIBC Theater (through May): The new playful and powerful Broadway musical focused on the six wives of Henry VII comes to the CIBC Theater.
Energy Revolution at the Chicago Architecture Center(through May): The newest exhibit at the Chicago Architectural Center highlights transforming the use of energy to actively respond to the climate crisis.
Chicago Craft Beer Fest(May 20 – 22): Craft beer lovers can enjoy sampling from over 40 specialty beers crafted by 35 different local brewers at this Fulton Market festival.
Japanese Film Festival by the Chicago Japan Film Collective (May 21 – 30): Join the Chicago Japan Film Collective as they present various in-person and virtual screenings celebrating Japanese filmmakers.
Mike Birbiglia at the Steppenwolf Theater (through May 22): Comedian Mike Birbiglia comes to the Steppenwolf Theater for his latest show The Old Man and the Pool.
Chicago Memorial Day parade(May 28): To commemorate Memorial Day, join the wreath laying ceremony at Daley Plaza, followed by a parade down State Street in the Loop.
