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Industry Showcase | The Lincoln Lodge | August 7
Chicago Italian Beef Fest | Jefferson Memorial Park | July 31 - August 2
Wigs | The Lincoln Lodge | August 6
Bronzeville Smooth Jazz Fest | August 1
Late Night at The Lodge | The Lincoln Lodge | August 6
Alison Wonderland at Concord Music Hall | August 1
Lollapalooza 2026 | Grant Park | July 30 - August 2
Windy City Comedy Fest Presents: Isabel Hagen
JACK GRADY AT THE COMEDY BAR | JULY 25
BASSMENT BEATS | EVERYTHING BAR | JULY 25
CHINATOWN SUMMER FAIR | July 25-26
FIESTA DEL SOL | PILSEN | JULY 23-26
WICKER PARK FEST | JULY 24-26
AUNTIE HAMMY AT THE COMEDY BAR | JULY 19
THEATER OF THE MIND | THE GOODMAN THEATER | JULY 17-19
TASTE OF RIVER NORTH | JULY 17-18
HIGHQ GAME SHOW AT RISE SALT SHED | JULY 17 | 7:30 PM
TACOS Y TAMALES FESTIVAL | PILSEN | JULY 17-19
Catch A Vine | VIN312 Winery | July 11 2:00-5:30 PM
Grant Park Music Festival | Grant Park | July 8,10-11
Carl Payne at The Comedy Club | July 11
The latest Chicago News
Chicago, IL — The Windy City Comedy Fest will return to Chicago from August 6–9, 2026 , bringing more than 50 comedians to venues across the city for four days of stand-up performances, showcases, and events celebrating Chicago’s thriving comedy community.
After building a reputation for blending alternative comedy, spirited competition, and cannabis culture into one uniquely interactive experience, HighQ: America’s Favorite Drug Test is launching a new weekly comedy & variety showcase in Chicago: HighQ Hangout.