Sweetest Day Comedy Jam

Sweetest Day Comedy Jam is coming to Wintrust Arena in Chicago, IL on October 17, 2026. Tickets start at $112.

Chicago hosts events at Wintrust Arena year-round. This comedy event is one of Chicago's upcoming picks - see all events in Chicago or browse Comedy events nationwide.

Before you buy

It is a Saturday evening show starting at 8:00 PM local time on a weekend.

Tickets start at $112, on the pricier side for Comedy in Chicago: the median starting price across the 65 Comedy listings we track there is $66, and 11% of them start higher.

Wintrust Arena has 25 other upcoming events on our calendar, including College (Div I-A And Div I-Aa) (20), Mixed Martial Arts (1), Pop / Rock (1). Next there: Taemin (Oct 21), DePaul Blue Demons vs. Notre Dame Fighting Irish (Oct 23), DePaul Blue Demons vs. West Georgia Wolves (Nov 2).

Same night in Chicago, cheaper

Sweetest Day Comedy Jam starts at $112. These Chicago events on October 17, 2026 start lower.

• Knox - Artist - House Of Blues - Chicago, 18:30: From $8 · Tickets →
• Northwestern Wildcats Women's Volleyball vs. Michigan State Spartans - Welsh Ryan Arena, 19:00: $10-$43 · Tickets →
• Jesse Welles - The Salt Shed Indoors - Chicago, 19:00: From $15 · Tickets →
• Chicago Wolves vs. Iowa Wild - Allstate Arena, 19:00: $22-$435 · Tickets →