Dinner, A Show, & Some Vino at City Winery

City Winery has taken the dinner and a show concept to new levels in New York, and it’s been so successful that they’ve just opened the first fully operational winery in Chicago. Just a short distance from the Loop in Randolph Street’s restaurant row is the new 33,000 square foot playground for adults. It’s a winery; it’s a restaurant; it’s a gigantic wine garden (5,000-of-those-square-feet gigantic), and it’s a performance venue. You can drink their wine; you can drink other vintners’ wines; heck – you can drink your own wine. You can have dinner before the show or during the show or when there’s no show at all, although with 20 – 25 shows a month you’d be hard pressed to come in on one of those nights.

The Venue

The space itself is divided into several areas. Outside is the above-mentioned wine garden, and inside is a sit-down restaurant and bar with a fireplace lounge, a mezzanine bar, private dining in the winery and in the private barrel room, and the performance venue. The decor is warm and elegant, with incredibly high ceilings, wood beams, exposed brick, and wine barrels everywhere. The performance space features its own bar, so you don’t have to wait too long for that next glass of wine.

The Wine

City Winery is Chicago’s first fully operational winery, so of course their wine selection includes their own. Illinois and New York, where the original location stands, are not known as great wine growing regions, so they source the grapes from all over. The finished product is then served through 18 tap lines that are attached to stainless steel kegs. 

In addition, they also have a list of around 400 wines from other producers, including a decent selection by the glass.

The Food

The menu is like a European and Middle Eastern sampler platter. Items include your choice of a trio of Mediterranean dips, funghi or paella rice balls, salumi flatbread and veal schnitzel. Small plates range from $5 to $15 and entrees average around $21 – $22.

The Shows

The talent they’ve secured for this space is where City Winery is really going to shine. They’ve opened this week with Lewis Black (sold out), and upcoming shows include Lindsey Buckingham, the Yardbirds, David Grisman Sextet, Shemekia Copeland, Sandra Bernhard and Suzanne Vega. All of them are performing for just 300 people on a proscenium stage, offering an intimacy not often found with these names.

In addition to the evening acts, every Sunday they’re hosting a Klezmer Brunch. Each week you can dine on lox, bagels, challah French toast and more while listening to Yiddish music. Tickets to the brunch are $10 and any food (and wine, of course!) is extra.

Whether it’s for dinner or a show or a glass of wine or all three, City Winery is Chicago’s newest spot for date night, girls night, guys night, or any night. And brunch, too.







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