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 fill custom juice boxes or 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 Andres Barrera's 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 and Barrel Room tasting bar, 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. Private dining rooms gather guests around long communal tables, stretched between exposed brick walls. In the show venue, comedians, live musicians, and slapstick-prone stage crew members entertain audiences under the glow of tabletop candles.