Chicago Wine Tastings & Tours
Discover Wines From The World’s Best Regions, Crafted Right Here in Chicago
Escape to Urban Wine Country
City Winery Chicago blends history, sustainability, and exceptional wine. We craft every bottle from grape to glass. Explore tastings, guided tours, and one-of-a-kind wine experiences—there’s something for every wine lover to enjoy.
Guided Wine Tastings
Join us for our wine tastings in Chicago, where our expert winemakers bring wine country to you. By sourcing exceptional grapes from the nation’s top growing regions, we craft remarkable wines right here in the West Loop. Led by one of our wine professionals, this guided wine tasting will take you through five wines as you explore new flavors, learn what makes each one special, and discover your new favorite pour.
Guided Wine Tastings are offered from 12pm - 5pm on Saturdays & Sundays. Walks-ins are welcome, but reservations are recommended. Please select the "Wine Tasting" dining option when making your reservation in Resy.
Weekly Winery Tour
Join us for an educational and fun experience as you take a guided winery tour and hear directly from the experts about how our wines are made at Chicago's only urban winery. Learn about our winemaking process, where we source our grapes, and the philosophy behind every bottle. Each tour takes around 30 to 40 minutes, and the guided wine tasting takes about 20 minutes. The Winery Tour and Tasting is $50 per person and includes a guided tour of our state-of-the-art winery and a curated tasting of five award-winning wines. Enjoy a complimentary cheese board and receive a one-time 20% discount on a retail wine purchase per guest. This is a perfect date or group activity - Book your tour today!
Wine Flights
Take a seat in our restaurant or bar and choose a curated wine flight, featuring hand-selected reds, whites, sparkling wines, and seasonal selections to pair with something from our wine-inspired menu. Whether you're exploring new styles or revisiting old favorites, wine flights are the perfect way to compare pours and find your next favorite glass.
What a Wine Tasting Looks Like
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. One of two membership tiers. See what's included in each.