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.
This weekend in Chicago is jam-packed with artisan markets, jaw-dropping art exhibits, riveting live theatre, family-friendly fun, exciting sports events, and so much more.
Check out just a few of the top things to do this weekend in Chicago, May 16 – 18, 2025.
Chicago Cabaret Week
This ten-day festival showcases Chicago’s top cabaret artists performing blues, Broadway, burlesque, jazz, R&B, American Songbook, French chanson, and world music. Get your tickets today!
3rd Fridays Free Admission Night
Free Admission Museum Nights take place every third Friday of each month from 5 pm to 8 pm! The tour will start at 6:00 pm…
Zhou B Art Center 3rd Friday
Zhou B Art Center opens exhibitions every 3rd Friday of the month with an evening reception from 7pm-10pm hosted by resident artists and galleries. This…
Beyoncé: Cowboy Carter Tour
Beyoncé returns to the stage for the COWBOY CARTER TOUR with three performances at Soldier Field May 15, 17 and 18!
Fourth Annual Pullman Railroad Days
Step into history at the Fourth Annual Pullman Railroad Days! The Fourth Annual Pullman Railroad Days is arriving May 17~18, 2025 with a station full…
Maxwell Street Market
Visitors to the Maxwell Street Market will experience an eclectic mix of foods and finds—including handmade crafts, resale housewares, clothing, and much more.
Hubbard Street Dance Chicago Season 47 Spring Series
Hubbard Street Dance Chicago (HSDC) closes out its thrilling 47th season with Spring Series, a dynamic program featuring a World Premiere by Matthew Rushing, Interim…
Buena Park PorchFest
Enjoy a Sunday afternoon strolling through Buena Park and enjoying live music on front porches, courtyards, and gardens while connecting with the community! Join us…
Big Bus Tours’ Sunset Live Tour
Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available now through Oct.…
Hiplet Ballerinas
Explore the fiery fusion of classical pointe technique, Hip-Hop and other dance styles with a Chicago trailblazing company redefining ballet with “cutting-edge style” (The University…
Trinity Irish Dance Company: Museum of Contemporary Art Chicago Engagement
The critically acclaimed Trinity Irish Dance Company kicks off their landmark 35th anniversary season with a series of performances at the Museum of Contemporary Art.  …
Anthony Hamilton & Vivian Green
Anthony Hamilton and Vivian Green will perform at The Chicago Theatre on May 17 with special guest Jadon Giuseppe!
Division Street Farmers Market
Support local farmers and eat fresh! Link Up Illinois (a program of Experimental Station) has been making it easier for Illinois residents to access fresh,…
28th Annual Asian American Showcase – FAAIM
Presented by The Foundation for Asian American Independent Media , this year's showcase is bursting with more AAPI talent than ever—from powerful films to side-splitting comedy!…
Windy City Margarita Fest
Windy City Margarita Fest is back, so mark your calendars! We’re serving up 15+ kinds of margaritas—from OG classics to new flavors that’ll hit just…
Urban Rappels at theWit
Conquer your limits at 278 feet up and rappel down theWit in downtown Chicago. Professional equipment provided and no experience needed. Trained experts guide participants…
Midwest Bonsai Society 19th Annual May Bonsai Exhibit
The Midwest Bonsai Society May Exhibit is pleased to announce that it is going into its 19th year in 2025. It is known for its…
North Suburbs
Event details
Hadestown
COME SEE HOW THE WORLD COULD BE. Welcome to HADESTOWN, where a song can change your fate. Winner of eight 2019 Tony Awards® including Best Musical…
Em Brown at The Comedy Bar
Em Brown began his comedy career while attending college in a small town in Southern Illinois. After graduating, he returned to Chicago, where he quickly…
ART on THE MART
ART on THE MART is one of the world’s largest digital art platforms that transforms an architectural landmark into a permanent, larger-than-life canvas. A shining example of Chicago’s long-standing commitment to public art, ART on THE MART brings cutting-edge video mapping techniques to Chicago’s Riverwalk, displaying projections of contemporary art across the 2.5-acre façade of THE MART.
Chicago Greeter InstaGreeter Walks of the Loop
InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago's top sights? Let InstaGreeter take you on a free hour-long guided…
Frida Kahlo’s Month in Paris
Don’t miss the first-ever exhibition of Kahlo’s work at one of the most renowned art museums in the world.
Dressed in History: A Costume Collection Retrospective
What do a red sequin burlesque costume, a pair of original Air Jordan 1s, a baby’s wool bathing suit, and an enormous white tulle Christian…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
