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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
Windy City Smokeout | United Center | July 8-12
Taste of Chicago | Grant Park | July 8-12
Vintage Culture at Lakefront Green | July 5
Barry Brewer at the Comedy Bar | June 5 | 8:00 PM
Camp Chicago | June 4
Navy Pier's 4th of July Fireworks | June 4 | 10:00 PM
WAMI's "The Lake House" Sundown Cruise | June 3 | 8:00 PM
Avatar Bending Yoga at Replay Lincoln Park | June 3 | 4:00 PM
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.