Ali Siddiq is performing live in Chicago on Saturday, November 14, 2026, at the Wintrust Arena. The celebrated master storyteller is bringing his brand-new stand-up routine to the city as part of Ali Siddiq: The Custom Fit Tour.
Venue
Never miss a night out
Weekly picks, new venues, and events like this — every Thursday.
You might also like
Afro Fusion All White Yacht Cruise
You're stepping onto the Anita Dee II dressed head-to-toe in white, ready to float across Lake Michigan while three levels of DJs spin everything from Amapiano to Afrobeats to dancehall—think less stuffy boat party, more floating festival with the Chicago skyline as your backdrop. The open-air top deck is where the energy peaks, but you'll find seamless vibes throughout, with international talent keeping the rhythm locked in until the sun dips.
DAD ROCK BRUNCH ft. Phil Angotti & Friends on FATHERS DAY!
DAD ROCK BRUNCH ft. Phil Angotti & Friends on FATHERS DAY! — live at Fitzgerald's Nightclub.
UNTITLED VAMPIRE PLAY
UNTITLED VAMPIRE PLAY — live at Lookingglass Theatre.