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.
One of the weekend’s highlights is Chicago Cabaret Week, when you can find performances from Chicago’s top cabaret artists with discounted tickets for $30 or less.
This weekend brings a ton of exciting happenings. Check out just a few of the events and happening in Chicago this weekend, May 15 – 17, 2026.
Chicago Cabaret Week
This annual ten-day festival showcases Chicago’s top cabaret artists performing blues, Broadway, burlesque, jazz, R&B, American Songbook, and international music. See more than 50 performers in intimate venues throughout Chicagoland, with discounted tickets for $30 or less.
5th Annual Lincoln Park Mayfest
As Chicago’s premiere summer kickoff event, Lincoln Park Mayfest is a lively celebration of the neighborhood’s spirit and talent. Enjoy performances from top local bands…
Lincoln Roscoe Art & Craft Fair
Friends of Lakeview welcomes all to the Lincoln Roscoe Spring Art & Craft Fair! Taking place between Roscoe and Melrose Streets on May 16 and…
Hyde Park Garden Fair
Since 1959, Garden Fair members have visited nurseries from Wisconsin to Indiana to select plants based on our own gardening experience and emphasizing varieties suited…
Hubbard Street Dance Chicago: Spring Series
To close Season 48 with vigor and verve, Hubbard Street brings a powerhouse program to the Harris Theater May 14, 15, + 17 featuring two…
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…
Les Misérables
STILL THE WORLD’S MOST POPULAR MUSICAL Cameron Mackintosh’s acclaimed production of Alain Boublil and Claude-Michel Schönberg’s Tony Award-winning musical phenomenon, Les Misérables, makes a triumphant return…
Pro Frisbee Game: Chicago Union vs Minnesota
Kick off summer in Evanston with the Chicago Union’s 2026 home opener on Saturday, May 16 at 6pm as they take on the Minnesota Wind…
Yellowcard – The Up Up Down Down 2026 Tour
Alt-rock band Yellowcard will perform live at The Salt Shed Outdoors on May 16, 2026.
Bruno Mars – The Romantic Tour
16-time Grammy winner Bruno Mars /w special guests Leon Thomas & DJ Pee.Wee will perform live at Chicago's Soldier Field on May 16-17, 2026.
Ari Lennox – Vacancy Tour
Ari Lennox is bringing The Vacancy Tour to Chicago for a performance at The Chicago Theatre on Saturday, May 16, 2026.
An Afternoon with David Sedaris
David Sedaris will perform in Chicago on Sunday, May 17, 2026, for a matinee event titled "An Afternoon with David Sedaris". David Sedaris, America’s best-selling…
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.
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…
1893 World’s Fair & Filming Locations: Chicago’s Midway Plaisance Walking Tour
Experience the history of Chicago’s Midway Plaisance on a Ph.D.-led walking tour that connects the 1893 World’s Fair to both early and modern-day filming locations.…
Yes, Chef! Chicago: A Bear-Inspired Food Tour
This is the ORIGINAL Chicago food tour that takes you to the restaurants featured on the TV phenomenon, The Bear. We'll take you to the actual…
American Prophets: Writers, Religion, and Culture
American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
