City Winery Chicago is a premier destination for stand-up comedy in Chicago, offering an intimate setting for unforgettable nights of comedy shows and live entertainment. Over the years, our stage has welcomed acclaimed comedians including Tiffany Haddish, Patton Oswalt, Kevin Nealon, D.L. Hughley, and Michelle Buteau, alongside a full lineup of touring and emerging talent. Beyond comedy, explore our show calendar of live music & entertainment including rock, R&B, jazz, and brunch shows, all paired with dinner service and award-winning wines.

Browse our schedule of Chicago comedy shows to discover upcoming performances and plan your next night out. Whether you're searching for live comedy in Chicago or a full evening of entertainment, City Winery Chicago delivers a seated experience here in the West Loop .