Visit us on Randolph St & Racine Ave

Join Us At Sea! January 24-31, 2027. Learn More

Early Access. No Fees. Monthly Wine Tasting Parties. Learn More

November - December

Holiday Season Lineup

Wood Harris, Ami Taf Ra & Kamasi Washington, DL Hughley, Mickey Guyton, Boney James, and many more!

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Live Music & Dining in The West Loop

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Escape to Urban Wine Country where concerts, comedy, wine, and food come together.

Gift Cards

Intimate Shows, Great Food, World-Class Wine - Give the City Winery Experience

Indulge Your Senses at City Winery

Shows
Wine
Dining
Private Events
Membership

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.

View Upcoming Shows

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.

Wine & Collectibles

Holiday Wine Specials

Have our wine shipped to your giftee's door. City Winery red, white, and sparkling wine.

Shop Wine

Merch Shop

Get cozy with a unique, one-of-a-kind City Winery hoodie or T shirt. No two are alike. 

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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

  • April 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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  • January 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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  • April 10, 2023

    "City Winery is on track to become the most environmentally efficient direct-to-consumer winery."

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  • February 2, 2023

    “City Winery to host fundraiser & performances in honor of Black History Month & Women's History Month”

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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.

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