Sommeliers are known for their ability to identify a wine's subtle flavors, a feat they accomplish by defragmenting the molecules with the bonus taste buds in their livers. Trust their gut with this Groupon.

$1,750 for a Private Gourmet Dinner and Wine Tasting for Up to 10 People ($4,299 Value)

• Private use of the Barrel Room (a $1,500 value)
• Spread of local or European cheeses, charcuterie, and crudités and six passed hors d'oeuvres followed by one salad, one entree, and one dessert for each diner (up to a $1,220 value)
• Guided tasting of three white wines and three red wines (a $400 value)
• Service from a dedicated team of servers, bussers, winemakers, sommeliers, and service fees (a $1,179 value)

The exact menu will vary by event, but may include hors d‘oeuvres such as marinated olives and wild-mushroom tarts, and entrees such as seared scallops or duck breast. Gratuity is not included.

City Winery

Michael Dorf stood with his brother Josh, smiling over the barrel filled with wine from grapes they'd just crushed, fermented, and pressed. He claims that despite tastings and classes, he'd never begun to understand wine until this moment. As his understanding grew, he laid the foundations for City Winery: a full winery facility, restaurant, and concert venue inside urban Chicago. He now watches over more than 400 international wines and 20 house wines. Inside the winery, these wines—made from nine US and international varietals—age inside stainless steel tanks and American and French oak barrels. Here, staffers lead winemaking classes, letting visitors join the crushing and fermenting process, and showing them how make private barrels and bottles pasted with labels of their own design.

These monolithic tanks and barrels can be seen through floor-to-ceiling windows from most of the restaurant's rooms, where servers ferry Executive Chef John Fuentes' dishes, each a blend of Italian, French, Spanish, and Middle-Eastern flavors. The culinary team crafts small and large plates of artisanal cheeses, seafood, and flatbreads—which they make using the winery's own wine lees as yeast. In the restaurant, staffers pour housemade wines piped fresh from the cellar through 14 taps, while visitors bask in the glow from hard wood and floor to ceiling windows. Patrons dine on a ground floor lit by soft blue lights and hanging lamps fashioned from old wine bottles, as well as a mezzanine level looking out on the city skyline. Versatile, private dining spaces can accommodate weddings, corporate events, or cozy wine-and-cheese gatherings. In the intimate, 300-seat music venue, comedians, live musicians, and slapstick-prone stage crew members entertain audiences under the glow of tabletop candles. Upcoming artists include "The Legendary Soul Man" Sam Moore, John Sebastian and Jimmy Vivino, and Suzanne Vega. The schedule is also packed with wine events, including Winemaking 101 and the Virtue Cider Dinner.