Sweetest Day Comedy Jam Tickets - Oct 18 - Wintrust Arena (Chicago)

Buy Sweetest Day Comedy Jam tickets from Vivid Seats and be there in person on Oct 18, 2025 at Wintrust Arena in Chicago.

If you’ve attended a Sweetest Day Comedy Jam event before, you know the excitement and energy of the crowd makes for a truly unforgettable experience. With Sweetest Day Comedy Jam tickets from Vivid Seats, you can experience it live.

Right now, Sweetest Day Comedy Jam tickets at Wintrust Arena for Oct 18 begin at $79. Sweetest Day Comedy Jam Chicago tickets have an average price of $345.

When you shop for Sweetest Day Comedy Jam tickets from Vivid Seats, you can purchase with confidence, knowing that all confirmed Sweetest Day Comedy Jam orders are backed by our 100% Buyer Guarantee.

Sweetest Day Comedy Jam tickets are available for Oct 18 but may also be available for other dates.

In addition to Sweetest Day Comedy Jam tickets at Wintrust Arena, Vivid Seats has tickets to other Comedy events. Vivid Seats can help you find Theater tickets for events in IL and anywhere else you’re hoping to be there in the crowd. When you purchase Sweetest Day Comedy Jam tickets (or any live event tickets) through the Vivid Seats app, you’ll start earning through our Vivid Seats Rewards loyalty program.