Best Places to Eat and Drink This Winter in Chicago

Check out some of Chicago’s top hot spots that are worth bundling up and going outside for — you can thank us later

Here are some venues worth venturing outside for this winter in Chicago.


We can’t stop the snow train from rolling into Chicago, but we can make it feel a little warmer inside our bellies with memorable dishes and drinks. Forget the beach and sun; we live in an epicurean paradise full of comfort foods and toe-tingling cocktails and wine. Check out some of Chicago’s top hot spots that are worth bundling up and going outside for — you can thank us later.

The Duck Inn (formerly the Gem-Bar Lounge, which served neighborhood cops and South Side folks) located in Bridgeport, is truly a hidden gem, especially because that brick-walled gem includes mod furniture and décor, trendy and friendly staff with hipster mustaches and black skinny jeans, and a B.Y.O.V. (bring your own vinyl) day. The food, as you might expect, is extraordinary. The Duck Inn, named as one of Esquire Magazine’s top new restaurants in America, earned a Michelin Bib Gourmand. Check out their brunch for specialty items created by Chef Kevin Hickey, like chai French toast, squash panzanella, funnel cake, and fried cheese curds. Also, don’t skip brunch staples, like a Bloody Mary or mimosa.

The Boarding House has class and sophistication written all over it. Proprietor and master sommelier Alpana Singh and executive chef Tanya Baker have created something magical here, a blending of stellar food and wine pairings that will keep you coming back for more. Try the beets and goat cheese salad, followed by the Copper River salmon, and end with the espresso gelato truffle. The wine list is quite extensive, and per the server’s recommendation, I had a glass of Peay Vineyards Pinot Noir from the Sonoma Coast in California and, honestly, I’ve been dreaming of this wine ever since.

Community Tavern in Portage Park, rated Best New Restaurant in 2015 by Chicago Magazine, is a cozy and charming French-inspired boutique steakhouse, which is very different from its nearby sister restaurant, the Portage — known for its new American and Asian-influenced dishes. At Community Tavern, a row of rustic birdcage chandeliers line the bar, there’s a private room with double doors in the back, and large front windows provide natural lighting and ambiance. Executive chef and partner Joey Beato came to Community Tavern after a stint at Momofuku Má Pêche in New York and Green Zebra in Chicago. Not to be missed: the Atlantic salmon and the Parisian gnocchi. Bar libations include Side Piece, Pamplemousse, and Fernet Daiquiri.

Wood in Lakeview has it all: good, shareable, small-plate food; fun cocktails with names like Suns Out, Guns Out and Strictly Platonic, and a location that makes meeting up with friends as easy as pie. Wood is the 2013, 2014 and 2015 winner of Michelin Bib Gourmands, and it’s a no-brainer to see how it’s earned this recognition. Chef Ashlee Aubin, formerly of Alinea, Home Bistro, and Zealous, brings years of experience to the table. Also, vegetables come from family farms like Green Acres and Three Sisters, pastas are made fresh by hand, and herbs and other ingredients are sourced directly from Wood’s private garden. Even the meat is butchered in-house.

Finally, if you really want to wow a date or have an indelible gourmet adventure, dine at Sixteen. You will be witness to the most beautiful and colorful arrangements and innovative dishes that executive chef Thomas Lents has to offer. This Michelin two-star, Forbes five-star, and AAA Five Diamond restaurant presents modern American cuisine like you’ve never seen before. Each course is paired with a thoughtful story that creates an entertaining experience worth the price of admission — you will walk away with more than a full belly. Plus, the restaurant’s 30-foot windows offer a remarkable view of our city — the Wrigley Clock Tower is so imposing that it looks like an image projected on a green screen.