Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.
Plus, it’s officially summer in Chicago, which means the city’s sandy beaches officially open to the public and festival season is in full swing.
This weekend brings a ton of exciting happenings. Check out just a few of the events and happening in Chicago this weekend, May 29 – 31, 2026.
Do Division Street Fest
Enjoy a diverse lineup of live music on two stages, food, shopping, and family-friendly activities during this annual street festival on the border of West Town and Wicker Park.
Maifest Chicago
Maifest Chicago in Lincoln Square brings food, dancing, and German culture, with live music and entertainment throughout the weekend.
Windy City Hot Dog Fest
Vote for your favorite frankfurter at the Windy City Hot Dog Fest, which will feature some of Chicagoland’s most iconic hot dog stands in a friendly summer competition.
Arte Agave Chicago
⭐ Experience the rich flavors and vibrant culture of Mexico at the Chicago Arte Agave Tequila & Mezcal Festival! Enjoy premium tequila and mezcal tastings, live…
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Crème de la Femme: An All-Femme Improv Festival
Finally, women are funny! On Friday, May 29 and Saturday, May 30, iO Theater is hosting Crème de la Femme: An All-Femme Improv Festival. As…
Rilo Kiley Live In Concert
Rilo Kiley is scheduled to perform in Chicago, IL, on Friday, May 29, 2026, as part of their reunion tour.
Chicago Dance Month Kickoff Celebration
Join See Chicago Dance in celebrating the kickoff of the 13th annual Chicago Dance Month! Taking place on Navy Pier’s iconic Lake Stage on May…
Chicago Stars FC vs San Diego Wave
Come see the Chicago Stars take on the San Diego Wave May 31 at 12 p.m. CST at Northwestern Medicine Field at Martin Stadium! In…
Street Foods of Pilsen Food Tour
Cruise with us down to the Lower West Side neighborhood of Pilsen that Forbes calls one of the “12 Coolest Neighborhoods Around the World” for…
Chicago Greeter – Loop InstaGreeter
If you're looking for a fast, flexible Greeter experience, check out our InstaGreeter walks. These hour-long guided walks are a fun and informal way to…
Millennium Park Summer Workouts
Participants are asked to bring their own workout mat The workout program takes place on the Great Lawn and Wrigley Square in Millennium Park on…
The Chinatown Adventure Food Tour
Immerse yourself in the vibrant flavors and rich history of Chicago’s Chinatown on our top-rated TripAdvisor food and culture tour. Enjoy seated dining at five…
Wicker Park Farmers Market
The Wicker Park Farmers Market will return on May 3 for its 26th outdoor season. The market will be open from 8 a.m. to 2…
Theater of the Mind
Now through July 12, 2026 Multiple experiences per day at the Reid Murdoch Building, 333 N LaSalle Visit TheateroftheMindChicago.com for dates, times, and tickets Created…
Matisse’s Jazz: Rhythms in Color
This exhibition marks the first time Matisse’s Jazz will be shown in its entirety at the Art Institute of Chicago. Jazz joins over 50 works from the museum’s renowned collection of paintings, sculpture, drawings, prints, illustrated books, and textiles.
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
