3
Upcoming Events
3
Comedians Performing
2
Months with Shows
Wintrust Arena Comedy Schedule by Month
October 20262 shows
November 20261 show
Upcoming Shows & Events at Wintrust Arena
Sunday, October 18, 2026
Bruce Bruce
Sweetest Day Comedy Jam
Get Ticketsvia ticketmaster
Earthquake
Cedric the Entertainer with Earthquake
Get Ticketsvia seatgeek
Sunday, November 15, 2026
Ali Siddiq
Ali Siddiq: The Custom Fit Tour
Get Ticketsvia ticketmaster
About Wintrust Arena
Wintrust Arena is a live entertainment venue located in Chicago, IL. The venue is located at 200 E Cermak Road.
The 2026 comedy schedule at Wintrust Arena features 3 upcoming events with 3 comedians performing, including Bruce Bruce, Earthquake, Ali Siddiq. The next event is on Sunday, October 18, 2026.
Check ticket prices from Ticketmaster to find the best deals on comedy shows at Wintrust Arena. Looking for more events? Browse all comedy shows in Chicago or all comedy shows in IL.
Frequently Asked Questions
What upcoming events are at Wintrust Arena?
There are 3 upcoming events on the Wintrust Arena schedule in Chicago, IL for 2026. The next event is on October 18, 2026.
What comedy shows are at Wintrust Arena this month?
There are no comedy shows scheduled at Wintrust Arena for September 2026. Check the full schedule for upcoming months.
What comedians are performing at Wintrust Arena?
Comedians with upcoming shows at Wintrust Arena include Bruce Bruce, Earthquake, Ali Siddiq.
Where is Wintrust Arena located?
Wintrust Arena is located at 200 E Cermak Road, Chicago, IL.
How much are tickets for events at Wintrust Arena?
Ticket prices vary by event at Wintrust Arena. Browse the schedule above and click "Get Tickets" to see prices from Ticketmaster.
How do I get tickets for comedy shows at Wintrust Arena?
Browse upcoming comedy shows at Wintrust Arena on StandUpdates and click "Get Tickets" for any show. We show prices from Ticketmaster to help you find the best deals.