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, Cinco de Mayo festivities, AAPI Heritage Month events, and more.
Top events in Chicago this May
Celebrate Mexican culture at Navy Pier (May 3 – 5): Head to Navy Pier for a free celebration of Mexican culture, bringing together music and dance performances, workshops, and over 30 vendors.
Take a tour of the historic Pullman neighborhood (May 5): Walk through history on this guided tour of the Pullman National Historical Park and surrounding area.
Attend the Asian American Film Showcase (May 17 – 23): This 27th annual film showcase provides a platform for new works by established and emerging Asian American filmmakers at the Gene Siskel Film Center.
Try a variety of cuisines during AAPI Restaurant Week (May 17 – 26): Discover a multitude of AAPI-owned restaurants across the city and suburbs, all offering special deals and discounts throughout the week.
Feast on Mexican cuisine at Mole de Mayo (May 24 – 26): Pilsen will be home to its annual outdoor mole cook-off, featuring an open-air mercado with local shops, music, dancing, and more.
See fringe theatre at Rhino Festival (Starting May 25): This year is the 35th annual Rhinoceros Theater Festival, Chicago’s longest-running fringe theater festival, when 50 artists showcase their plays, music, and art throughout six venues across the city.
Feel the beat at Suenos Music Festival (May 25 – 26): Head to Grant Park for a two-day Latin music festival that features a variety of Reggaeton and Latin performers, as well as art, activities, a Ferris wheel, and more.
Be dazzled by the Navy Pier fireworks (starts May 25): Kick off the summer with the first fireworks display of the season at Navy Pier over Memorial Day weekend.
See acclaimed documentaries during Doc10 (May 2 – 5): This documentary film festival brings exciting premieres and shorts to the Davis Theater and Gene Siskel Film Center.
Get carried away by Chicago cabaret (May 10 – 19): Back for its second year, Chicago Cabaret Week brings discounted tickets to a variety of blues, jazz, American songbook, and Broadway performances.
Cheer on the Chicago Sky (May 25): The city’s celebrated WNBA team opens their regular season at Wintrust Arena against the Connecticut Sun.
Celebrate house music history (May 30): This free event at the Chicago Cultural Center puts a spotlight on Chicago’s house music scene, with a documentary screening, workshops, and performances.
More events in Chicago this May
Cheer on the Chicago Fire at Soldier Field (through May): Feel the thrill of live soccer as the Chicago Fire takes the field at their home stadium on the lakefront.
Attend a unique performance at Hyde Park Art Center (May 4): Creative performers will present an experiential movement and sound workshop, inspired by traditional ring shout rituals, at the Hyde Park Art Center.
Get zen at Lincoln Park Zoo (May 4): Enjoy a sound meditation during this hour-long immersive experience inside Pepper Family Wildlife Center.
Go on a kayak tour of the Chicago River (through May): Choose from an informational architecture tour or a scenic sunset paddle with these kayak excursions, no experience required.
Vibe to house music during Sunday Service (May 4): This free outdoor performance at Kenwood Gardens features DJ Duane Powell showcasing the best of house music.
Celebrate Cinco De Mayo with a walking tour (May 4 – 5): Hop on a bus tour with Dilla, Chicago urban historian and social media personality, for a deep-dive tour of Pilsen and Little Village in celebration of Cinco De Mayo.
Shop the Wicker Park Farmers Market (starting May 5): This year marks the 24th season of the Wicker Park Farmers Market, bringing together over 50 local and regional vendors selling vegetables, fruit, flowers, meat, cheese, coffee, and more.
Bring your inner kid to Camp Hide N Seek (May 4): The Chicago Children’s Museum hosts this special one-night-only after-hours event for the adults, with cocktails, bites, music, and camp-inspired activities.
Head to Andersonville for a Wine Walk (May 11): What better way to explore this charming neighborhood than with sips of wine along the way? The annual Andersonville Wine Walk includes multiple restaurants and wine bars offering tastings.
Take the family to a Mother’s Day Tea Party (May 11): Enjoy music, crafts, and plenty of tea to go around for this special Alice in Wonderland-inspired tea party in Normandy Park.
Head to the Garfield Park Conservatory for spring blooms (through May 12): The spring flower show at this historic conservatory explores botanical nomenclature while showcasing the season’s most beautiful blooms.
Catch a movie outside Wrigley Field (May 15 and 29): Free movie nights return to Gallagher Way this May, starting with the Super Mario Brothers Movie and High School Musical 2.
Explore the science behind being a spy (through May): The newest exhibit at the Museum of Science & Industry, 007 Science: Inventing the World of James Bond, features the iconic cars, gadgets, and props of the famed James Bond films over the years.
Kick off spring at Mayfest (May 17 – 19): Street fests are in full swing in May, and Lincoln Park’s Mayfest is no exception. Live music, an art show, and plenty of food and drink make for a picture-perfect weekend.
Browse the Lincoln Roscoe Arts + Craft Fair (May 18 – 19): Lincoln Avenue will host over 70 local artisan vendors at this spring craft fair in Roscoe Village.
Step inside Frank Lloyd Wright gems (May 18): Architecture lovers won’t want to miss this unique opportunity to tour original Frank Lloyd Wright designs during this annual event in Oak Park.
Shop the Renegade Craft Fair (May 18 – 19): Over 200 artists and vendors will showcase their works of art, jewelry, design, crafts, and more at this Andersonville fair.
Sing along with Mamma Mia! (through May 19): The beloved ABBA-inspired musical comes to Chicago for a limited run, telling the story of a mother-daughter duo filled with love, laughter, and plenty of great music.
Hear live music at the Belmont Sheffield Music Fest (May 24 – 26): This year is the 39th annual edition of this Lakeview music festival. Local tribute bands will take the main stage, with plenty of options for food and drink.
Bring the kids to meet Bluey (starting May 25): Step into a real-life episode of Disney’s Bluey with an immersive experience that includes Bluey’s house and character meetings.
Pay tribute at the Chicago Memorial Day parade (May 25): To commemorate Memorial Day, join the wreath-laying ceremony at Daley Plaza, followed by a parade down State Street.
Check out the Randolph Street Market (May 25 – 26): One of Chicago’s biggest street markets returns to the West Loop with thousands of nationwide vendors selling antique goods, art, vinyl, jewelry, and so much more.
Toast to craft beer at Mayfestiversary (May 25 – 26): Two beloved neighboring breweries, Begyle Brewing and Dovetail Brewing, come together for this annual spring celebration.
Enjoy live tunes at Jazz’n on the Steps (May 26): The Southside Jazz Coalition presents Jazz’n on the Steps, a free community concert in the Greater Grand Crossing neighborhood.
Attend a candlelight concert (through May): These candlelight concerts in unique venues across Chicago feature string quartet performers, performing homages to Queen, Pink, Adele, and Coldplay.
See the spectacular ART on THE MART (through May): This nightly art and light installation is back with new original works displayed each night along the Chicago River.
Explore the Adler Planetarium at night (through May): On Wednesday evenings, head to the Adler Planetarium for special late-night hours and free admission for Illinois residents.
Expand your mind at the Chicago Humanities Festival (through May): The Chicago Humanities Festival presents over 60 conversations and performances from an array of talent, including Jen Psaki, Amy Tan, Andrew Bird, and many more.
Eat and drink at Lincoln Park Greek Festival (starting May 31): Lincoln Park’s annual Greek Festival will bring together authentic Greek flavors, music, sounds, and traditions for a weekend of family-friendly fun.
