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Sugar&Spice: City Winery
by Meghan Streit

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When I first heard about City Winery—a West Loop spot that is at once a working winery, 300-seat concert venue and full restaurant—I was a bit skeptical. I'm generally a believer that you can't be all things to all people, and so I figured City Winery would excel at one of its goals, but be lackluster in the other departments. Boy, was I wrong (and pleasantly surprised!).

I had my first full City Winery experience in November when one of my favorite artists, Rachael Yamagata, played at the venue. Instead of standing on tired tiptoes to see the stage, I was seated comfortably in a chair and could hear every beautiful word. Glasses of robust Sonoma zinfandel replaced the watery overpriced beer I'd normally be forced to drink at a concert. Somewhere around Yamagata's third song, as I stuffed myself with delicious Burrata cheese spread on crusty toasted bread, a waitress appeared quietly to set down a fresh glass of wine in front of me, and I thought to myself, "This place is a freaking urban amusement park for adults!"

I had seen Yamagata perform several times before, and I initially thought I'd miss the grit of being at a rock concert. Nope. As it turns out, standing in a long line and then missing your favorite song to pay $9 for a crappy beer actually sucks. Eating delicious food and drinking high-quality and reasonably priced wine while you listen to your favorite artist is such a superior concert experience. Obviously, Chicagoans aged 30 and above are going to love this place. But, you don't have to have wrinkles to enjoy City Winery. I was sat next to two University of Chicago students at the Yamagata show, and they seemed to enjoy the experience as much as I did.

Chicago's City Winery is the second location. There's also one in New York, and from what I've read, the Chicago location is bigger and better. I haven't been to the Big Apple location, but the Second City version is positively visually spectacular. Thirty-foot ceilings, walls lined with wine bottles and huge stainless-steel wine vats behind the bar make the space stunning. Exposed brick, colorful artwork and a fireplace in the middle of the main dining room make it cozy.

You can dine at City Winery any day of the week, and you should. But, if you opt to have dinner and see a show, then you are in for a real treat, albeit a pricy one. Depending on your appetite for lovingly crafted glasses of wine, you can easily drop $200 on a meal for two. If you're seeing a show, it's recommended to arrive about an hour early if you'd like to have dinner. The idea is that you'll be finishing up your meal, perhaps lingering over dessert, as the show gets underway.

Seating is tight because, hey, you're getting a fine dining experience in a concert venue. I like my space, so I was a teensy bit irritated at first, but I was happy to have a chair at all, and my fiancée and I ended up chatting with our tablemates and had a great time.

After you're settled with a glass of wine—there are nearly 100 to choose from, but I'd recommend sampling one of City Winery's own varietals that are "on tap"—then it's time to dig into the menu. The concert venue menu is a smaller version of the restaurant's main menu. You'll find a nice selection of small plates that are well thought out and made with fresh and just downright tasty ingredients. Smaller items average about $6 a pop, and the heartier dishes cost around $12 each. Four to five dishes will satisfy—but not stuff—a party of two. But so many sound tempting, so I wouldn't blame you for ordering more than that.

I have a mid-level obsession with City Winery's Burrata, as I discussed in my last column ( ). The cheese itself is impossibly soft and creamy, but what makes it so memorable is the bread it's served with. The crusty Italian bread is slathered with a generous dose of olive oil, dusted with herbs and then toasted to perfection. It's the perfect start to a lovely meal. Other lighter and highly sharable plates include white bean and garlic dip served with pita and an assortment of arancini balls (fried risotto) that I'm dying to try.

I also tried the salame flatbread, which was basically to die for. The light and crispy crust was phenomenal, and the sopressa and smoked mozzarella worked in perfect harmony as toppings. This pizza pairs nicely with City Winery's slightly spicy house zinfandel.

Among the more entrée-like offerings is a braised short rib with creamy rosemary polenta. In a culinary world now saturated with braised short ribs, this one definitely stands out. The meat was infused with so much flavor and was ridiculously tender. The polenta makes a perfect companion, and a dollop of tomato compote gives the dish a little extra zing. If you want to sneak a vegetable into your meal, the cauliflower gratin is a delightful way to do it. The cauliflower is baked beneath a gooey and piping-hot layer of Gruyere, Mornay sauce and toasted breadcrumbs (which perhaps disqualifies it as a vegetable, but who the heck cares?). The portion was quite small, and when Gruyere is involved, I don't like to share, so next time I'll order my own cauliflower gratin.

Not that I needed any more calories at this point, but midway through the concert, dizzy with the special happiness that can only come from drinking good wine and listening to great music, I decided to order the City Winery sliders as a late-night snack. They are served simply on pretzel rolls with lettuce and tomato. The burgers themselves tasted eerily like the ones my dad used to grill in the backyard when I was a kid. So, either my dad is a secret culinary genius or these burgers are fairly average. I think the sliders could have benefited from some cheese or some sort of a secret sauce, but nonetheless, I happily gobbled them up just like I did at backyard barbeques as a child.

If you're looking to treat yourself or impress someone special with a truly lovely evening, City Winery is the place to do it. The dinner and concert I enjoyed there was sincerely one of the best nights out I've had in a long time, and I'll be hoping that all of my favorite musicians book gigs there, so that I have many excuses to return to City Winery.

City Winery is located at 1200 W. Randolph St.; call 312-733-WINE or visit

Do you need some more Sugar & Spice in your life? Follow me on Twitter @SugarAndSpiceMS for inside scoop and commentary on Chicago's dining scene.

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