An elegant Valentine’s Day wine experience in the heart of Chicago
Spend Valentine’s Day learning how five wines and artisan chocolates change each other’s flavor profile in an intimate, behind-the-scenes Chicago tasting. This short, guided experience is perfect for couples or small groups who want a focused, sensory-driven outing without leaving the city.
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Difficulty
easy
Duration
1–1.5 hours
Fitness Level
Minimal physical exertion; fine for most adults who can stand for short periods or sit at a bar.
Wildlife
History
Chicago’s food and drink culture evolved alongside its lakeside trade routes; intimate tastings reflect the city’s craft-forward culinary movement.
Conservation
Choose low-intervention or locally sourced wines when offered and minimize single-use items; consider transit options to reduce the visit’s carbon footprint.
Chicago Winery
An elegant Valentine’s Day wine experience in the heart of Chicago
Chicago Winery is an urban winemaking destination located in Chicago, Illinois that offers guided tours, tastings, and themed events. The winery operates a production space and barrel room where guests can see winemaking from grape sourcing through fermentation and bottling. Chicago Winery’s public experiences include a Date Night for Two with a curated dinner reservation and two glasses of wine, a Wine Tour & Tasting featuring tastings of five wines, and seasonal events such as Spooky Sips that pair candies with wines for a playful Halloween tasting.
Tours and tastings are led by on-site staff who explain the production process, tasting techniques, and pairing principles in an accessible format suitable for first-time wine visitors and experienced enthusiasts alike. The facility’s tasting flights focus on five specially selected wines served in the winery, production area, and barrel room, providing a hands-on perspective of urban winemaking in the city.
Visitors can expect structured tastings, an opportunity to view production equipment and barrels, and options that combine tasting with local dining. Chicago Winery focuses on educational, entertaining experiences designed for couples, groups, and seasonal audiences. The business is based in Chicago, Illinois and centers programming on the craft of winemaking and the local urban setting. For those planning an evening out or a themed celebration, Chicago Winery offers distinct experiences that showcase wine education, tasting, and an authentic look at small-scale urban wine production.
Visitors can book experiences directly through tour listings and coordinate dinner reservations with nearby partner restaurants for special occasions.
Location
Chicago, IL
Located in Chicago, Illinois
Tours Offered
3 Tours
Public experiences available
Tasting Flights
5 Wines
Five wines per tasting
Events & Themes
Seasonal
Includes Spooky Sips and Date Night
Choose Date Night, Wine Tour & Tasting, or seasonal Spooky Sips — book a visit in Chicago today.
Reserve early
Valentine’s slots sell out—book well in advance and confirm group size to secure a preferred time.
Bring valid ID
You must present government-issued identification to participate in the tasting and to purchase alcohol.
Plan transit for evenings
Street parking is limited in central neighborhoods; consider transit or rideshare for a stress-free return.
Take notes
Bring a small notebook or use your phone to record favorite pairings and tasting notes for later reference.
Valid ID
Required for alcohol service and proof of age.
Comfortable shoes
You may stand or walk short distances between tasting and production spaces.
Notebook and pen
Useful for jotting tasting notes and pairing ideas to recreate at home.
Warm layers
Chicago winter evenings are cold; a coat or warm layer makes arriving and leaving more comfortable.
winter