Visit us on Randolph & Racine in the West Loop
Join Us At Sea! January 24-31, 2027. Learn More
Early Access. No Fees. Monthly Wine Tasting Parties. Learn More
Harvest Season Lineup
Ruthie Foster, Damon Williams, MC Lyte, Bob Schneider, and many more!
Live Music & Dining in The West Loop
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Escape to Urban Wine Country where concerts, comedy, wine, and food come together.
What's Happening at City Winery
Harvest Season
Celebrate Harvest Season at City Winery Chicago with live shows, guided wine tastings, and hands-on experiences that bring you closer to the winemaking process. Go behind the scenes with a Harvest Winery Tour, explore the craft through Crush Camp, or taste your way through a curated selection of wines while experiencing the most exciting season of winemaking.
Live Music & Comedy
Experience live music, concerts, and stand-up comedy at City Winery Chicago, featuring touring artists, established favorites, rising talent, and top comedians throughout the year. From rock concerts and live R&B to jazz, soul, folk, comedy shows, and more, our stages offer something for every audience. Settle in with dinner and award-winning wines while enjoying your performance from a seat with great sight lines.
Wine Tastings & Tours
Explore guided wine tastings at City Winery Chicago, led by our wine professionals and featuring a curated selection of wines as you discover varietals, growing regions, flavors, and winemaking techniques. For a closer look at the winemaking process, go behind the scenes with a winery tour to learn how we craft our wines through the journey from grape to glass. Discover the craft behind every pour and explore our wines in our wine shop and online.
Restaurant & Concert Dining
Indulge your senses at City Winery Chicago, where chef-crafted dishes and fresh, seasonal ingredients come together with award-winning wines. Join us for restaurant dining here in the West Loop with a menu of small plates, shareable dishes, and satisfying entrées prepared with wine pairing in mind. During a show, enjoy concert dining with food and wine served right to your seat throughout the performance.
Celebrations & Company Events
Plan your next private event at City Winery Chicago, with versatile event spaces in the West Loop for weddings, corporate events, holiday parties, milestone celebrations, and more. From chef-driven menus and handcrafted wine to flexible spaces and built-in production capabilities, our team brings food, wine, and entertainment together to create a memorable setting for gatherings of all sizes.
Vinofile VIP & VIP+
Get more from City Winery with Vinofile VIP and VIP+, memberships created for music and wine lovers. Enjoy benefits like early access to shows, no ticket fees, rewards on food and beverage purchases, and more. Upgrade to VIP+ for exclusive wine benefits, including monthly tastings, featured wines, wine flights, retail discounts, and special winery experiences.
Our Restaurant
Brunch
Saturdays & Sundays 10AM-3PM
Make City Winery your weekend brunch spot. Every Saturday and Sunday from 10 AM–3 PM, enjoy brunch classics and a DIY mimosa bar.
Burgers & Barrels
Sunday through Thursday
Burger + Glass of Tap Wine Pairing for $25
Looking for more pairing inspiration? Read The Case for Your Summer BBQ to discover our favorite wines for burgers, barbecue, and all your summer grilling favorites.
Happy Hour
Mondays - Thursdays 4PM-7PM & Fridays 2PM-5PM
Enjoy $10 Tap Wine of our Rosé & Sauvignon Blanc as well as $10 Featured Cocktails and half off of our small bites! Start with our guide to what pairs best with dinner.
Chef & Winemaker Dinners
Each month brings a new themed, multi-course menu paired with carefully selected wines to complement every dish. Explore seasonal flavors and wine pairings designed to bring each course to life.
City Winery is Going to Sea!
Join us on the Journey of Jazz Cruise
January 24-31, 2027
This January, City Winery is teaming up with Journey of Jazz for a floating festival unlike anything we've done before, bringing the live music, wine and hospitality you love from our venues onto the open water.
On Tap: Musings on Everything City Winery
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Dinner Party Trio: A Harvest Dinner in Three Pours
Dinner Party Trio is our new series: three City Winery wines chosen to follow one another through a single evening, each paired with recipes, so you have everything you need...
Dinner Party Trio: A Harvest Dinner in Three Pours
Dinner Party Trio is our new series: three City Winery wines chosen to follow one another through a single evening, each paired with recipes, so you have everything you need...
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Chicago Deep Cuts Fall 2026
Fall in Chicago has a way of turning the calendar into an argument for staying in the city instead of leaving it, and this stretch of the City Winery lineup...
Chicago Deep Cuts Fall 2026
Fall in Chicago has a way of turning the calendar into an argument for staying in the city instead of leaving it, and this stretch of the City Winery lineup...
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September Specials and How to Pair Them
This month's specials are on the board at every City Winery location, and there's a pour, or a few, in each market's wine program built to sit right alongside them.
September Specials and How to Pair Them
This month's specials are on the board at every City Winery location, and there's a pour, or a few, in each market's wine program built to sit right alongside them.
Wine & Collectibles
Harvest Season Exclusive
Receive an invite to our exclusive Thanksgiving Wine Tasting in early November when you purchase our Harvest Case or Half Case.
Merch Shop
Get cozy with a unique, one-of-a-kind City Winery hoodie or T shirt. No two are alike.
Vinofile VIP+
The Wine Club for Music Lovers
Every month, attend exclusive wine parties with a friend, take home a bottle of our featured wine, enjoy a complimentary wine flight, plus always get 48-hour early access to tickets and pay no fees.
Press
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Read MoreApril 20, 2026
"City Winery founder Michael Dorf talks about building two iconic music businesses from nothing and why sleeping under your desk is sometimes the right move."
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Read MoreJanuary 5, 2026
“Michael Dorf reflects on the evolution of City Winery, the rise of comedy programming, new restaurant concepts including El Bar, and the future of live music.”
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Read MoreApril 10, 2023
"City Winery is on track to become the most environmentally efficient direct-to-consumer winery."
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Read MoreFebruary 2, 2023
“City Winery to host fundraiser & performances in honor of Black History Month & Women's History Month”
Private Events
Host your next event at City Winery! Our unique, urban winery offers everything you need to make your next event an unforgettable experience.