City Winery Chicago is an urban winery in Chicago's West Loop that produces small-batch wines onsite using premium grapes. It combines live music concerts, stand-up comedy shows, a restaurant with Mediterranean-inspired cuisine, and private event spaces. Guests can enjoy winery tours, tastings, and pairings in a vibrant venue perfect for nights out or special occasions.

Urban winery with live music and comedy Onsite small-batch wine production Wine and food pairings Private events
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Spring season lineup promo Dining area Winery tours and tastings Spring wine 6-pack
Spring Wine 6-Pack
Go-to for effortless spring entertaining. Save $25 and free shipping.
Spring Season Lineup
March - May 2026
Lyle Lovett, Eric Bellinger, Amy Grant, Gospel Melodies Brunch, Mom's Night Out, Jeff Mauro, and more.
Brunch
Saturdays & Sundays 10am - 3pm
Brunch classics and DIY mimosa bar.
Burgers & Barrels
Sunday through Thursday
Burger + glass of tap wine pairing for $25.
Happy Hour
Monday through Friday 4-7pm
Half-price wines on tap, flatbreads, dips.

Press: Michael Dorf on building music businesses (Apr 20, 2026); City Winery evolution, comedy, new concepts (Jan 5, 2026); Most environmentally efficient DTC winery (Apr 10, 2023).