About
City Winery Chicago is an urban winery in Chicago's West Loop combining live music concerts, stand-up comedy, a restaurant with Mediterranean-inspired cuisine, and private events. They produce small-batch wines onsite using premium grapes, offer tours and tastings paired with charcuterie, and feature wines on tap alongside global selections. Specialties include brunch, happy hour, and a wine club for music lovers with exclusive perks.
Urban winery with live music and comedy
Wines on tap
Mediterranean-inspired cuisine paired with wines
Winery tours and tastings
Photos
What They Make
Spring Wine 6-Pack
Go-to for effortless spring entertaining. Save $25 and Free Shipping.
Awards
Best Urban Winery, Chicago Reader 2020
2020
Upcoming Events
Spring Season Lineup
March - May 2026
LaRoyce Hawkins, Regina Belle, Howie Day, Twista, Lyle Lovett, Fred Hammond, Eric Bellinger, Vanessa Carlton, and more
Brunch
Saturdays & Sundays 10am - 3pm
Brunch classics and DIY mimosa bar
Happy Hour
Monday through Friday 4-7 pm
Half-price wines on tap, flatbreads, dips with pita
Latest News
January 5, 2026: Michael Dorf reflects on the evolution of City Winery, rise of comedy programming, new restaurant concepts, and future of live music.