By Kelly Cunningham

My night at City Winery began with the wrong address and a longer-than-expected walk in a jacket I thought would be warm enough. Once I figured out the correct address, we walked down Randolph’s famous restaurant row feeling reassured. The glass walls of City Winery glowed with warmth at the end of the block. Even from the opening foyer, the clean lines and contemporary style made it clear I was in for an elegant evening.

The restaurant is divided into several sections, each catered toward a different type of experience. There’s a large dining area with glossy wooden tables and comfortable chairs, a bar with honeycomb shelves filled with wine bottles, and the special performance room (where we were heading) that frequently hosts live music and stand-up comedy performances. The hostess led us to our seats and we began to look over the menu as the first act got underway.

Most guests were dressed up but generally seemed laid-back, the music was fun and folksy, and the pinot noir we finally settled on was amazing.

We shared our four-person table with another fellow, a friend of the second musician. Our table was on the lower level, where the seats were arranged in rows facing the stage. Though being close to others while dining may seem less than ideal, it actually had the effect of creating a community during the performance. The crowd was enthusiastic, singing along as they sipped fine wine and nibbled on their appetizers and dinners. We pondered over the long list of wine and admired the scene around us. Most guests were dressed up but generally seemed laid-back, the music was fun and folksy, and the pinot noir we finally settled on was amazing.

The first musician, Seth Walker, bantered with the audience and entertained with traditional Americana instrumentation and timely lyrics. His songs covered everything from sad stories of modern-day racism to playful tales of bad tattoos. Walker was followed by Edward David Anderson, who had guests dancing by the end of his first song. His more bluesy style kept the energy in the room alive throughout the rest of the night.

Good food and good wine were expected at City Winery, but what really made the venue stand out was the atmosphere it creates. Ambient lighting and understated interior design make its luxuriousness seem effortless. With modern art on one wall, exposed brick on the other and candlelit tables in between, City Winery is equal parts cool, comfortable and classy.

City Winery is located at 1200 W. Randolph in the West Loop. They have a second location along Chicago’s new Riverwalk off of Wacker Dr. www.CityWinery.com