Chicago’s Best Wine Bars

Raise a glass to these favorite neighborhood spots

Whether you’re savoring just a glass or popping open an entire bottle, Chicago has a plethora of options for those looking to enjoy wine in the Windy City. With casual spots for the occasional drinker to some of the best bottles for serious oenophiles, unwind and enjoy everything from flights to porróns at these best wine bars throughout the city.

LOGAN SQUARE: Webster’s Wine Bar

Opened in 1994, Webster’s has long been a beloved mainstay of the Chicago wine scene. This European-style wine bar moved to its new digs in 2014, settling into a cozy corner spot in the trendy Logan Square neighborhood, where they serve up a rotating selection of a few dozen wines to enjoy either as a tasting portion, by the glass, or by the bottle. Their offerings are from around the globe, and include over 500 wines in their cellar, showcasing numerous organic and biodynamic options, with an overall focus on ethically-made wines. A tailored food menu features a variety of bites, small plates and entrees. The bar also often celebrates a variety of seasonal wine events and hosts weeknight specials where you can score deep discounts on high-end pours. 2601 N. Milwaukee Ave, 773.292.9463


Income Tax has elevated the casual neighborhood wine bar game with a European leaning wine list and a curated global menu that has garnered awards and critical praise since they opened in Edgewater in 2016. The dark, intimate space offers a rotating list of wines by the glass and a wide selection of bottles, but also offers guest a unique drinking option not seen elsewhere. The bar will open most offerings on their wine list as a half serving, the perfect way for vino lovers to enjoy a few glasses of a wine typically out of their price range. Also save room for some eau-de-vie, a clear fruit brandy that isn’t a typical focus of most bar programs but is offered here under their impressive list of fruit spirits. Dinner is a must with Chef Ellison Park at the helm in the kitchen, whose dining has been the focus as beloved and revered spots like Parachute and Lula Café. 5959 N. Broadway, 773.897.9165


As the first wine bar from the Lettuce Entertain You dining empire, Bar Ramone is a new addition to the local scene that has quickly established itself as a standout place to enjoy vino in Chicago. Like walking into a bar in Barcelona, the menu and space give some serious Spanish flair. You can order a porrón, a traditional Spanish drinking vessel filled with Txakoli, a low alcohol wine that is common in the Basque region. A menu of small plates include pan con tomate, a traditional Spanish-style tomato bread, plus a variety of Spanish hams and cheeses, pintxos and a fresh selection of seafood from acclaimed chef Hisanobu Osaka. The man behind the carefully curated beverage program is Richard Hanauer, who previously oversaw the programs at the RPM Restaurants and was once named one of Food and Wine’s sommeliers of the year. He’s a rockstar in the wine world that all but guarantees you’ll be drinking some of the best pours around. 441 N. Clark St, 312.985.6909

LOGAN SQUARE: Table, Donkey and Stick

At the border of Logan Square and Humboldt Park you’ll find Table, Donkey and Stick, an award winning neighborhood spot that specializes in the cuisine traditions of the Alps. Their beverage program puts a focus on rare small-batch wines, even listing a selection of oddballs on the menu for adventurous drinkers. Table, Donkey and Stick has carved out a cult following in the local wine scene with their popular Terroir Tuesdays series. Every Tuesday the bar features a special wine or wines by the glass at wholesale cost, with past wines including impressive names and hard-to-find, by the glass pours at unheard of prices. Don’t skip out on their burger, which was recently named one of the best in the city, that features raclette, shiitake mushrooms, roasted onions and dijonnaise on a pretzel bun. 2728 W Armitage Ave, 773.486.8525

HUMBOLDT PARK: Rootstock Wine & Beer Bar

Long before the corner of Augusta Boulevard and California Avenue became the hub of culinary delights that it is today, Rootstock has been serving up a thoughtful beverage program and seasonal food menu in this west side neighborhood since 2009. With a focus on small production wines and beer, you’ll find a variety of under-the-radar adventurous pours at Rootstock, with offerings from around the world including Greece and Slovenia. If you’re a sherry or port fan, they have a hearty menu of fortified wines, and don’t sleep on the beer options either. Rotating drafts include local small brewery selections, and a variety of cider and fruit beers that aren’t usually on tap at most bars. The seasonal food menu spotlights local purveyors, including one of the best burgers in the city—a dry-aged Slagel Farms beef topped with bacon aioli and cheddar. 954 N. California Ave, 773.292.1616

WEST LOOP: The Press Room

The Press Room is a cozy, 70-seat wine bar in the West Loop situated below Publishing House, a bed and breakfast housed inside a century-old building that began as a former Methodist publishing house. The interior of Press Room pays homage to the building’s past with vintage photographs and artwork, while diners enjoy a seasonally driven menu that compliments a wide selection of wines by the glass and an impressive bottle list from around the globe. The Press Room also offers membership to their Fourth Estate Wine Club. With this personalized program, the sommelier will hand-select one hard-to-find, unique bottle based on a member’s questionnaire and price point, and they’ll e-mail when your monthly pick is ready for pickup. 1134 W. Washington Blvd, 331.240.1914

BUCKTOWN: Red & White

In recent years, natural wine has exploded in popularity across the globe and one of the best places to find these trendy pours is at this neighborhood gem. Housed in the booming Bucktown area just steps away from the relaxing 606 elevated park, Red & White is modeled after popular natural wine bars found throughout Paris, with an minimalist yet intimate design that encourages people to converse while exploring the extensive collection. Unfamiliar with natural wine? No worries, Red & White hosts weekly complimentary tastings where you can learn about these unique pours and their eco-friendly methods of production. After settling on something to drink, check out Red & White’s menu of small plates with dishes like classic cheese boards and roasted carrots. 1861 N. Milwaukee Ave, 773.486.4769


Located in the heart of the trendy Ukrainian Village neighborhood, All Together Now! is a funky and eclectic space full of retro décor where you can grab a bottle to go or settle in to enjoy a quick bite from an all-day menu that spotlights seasonal Midwestern fare. All Together Now! is home to an impressive wine club as well. Membership gets you two bottles of wine each month, complimentary tastings for you and a friend during monthly wine club pickup events, a discount on retail purchases in their market, no corkage fee while dining in house and first dibs on access to new releases and limited offerings. And to keep you from breaking the bank, their wine club has two membership tiers and you can join for just three or six months. After a few glasses, take a quick walk nearby and check out one of the city’s hidden gems—the Ukrainian Institute of Modern Art. 2119 W Chicago Ave, 773.661.1599

RIVER NORTH: Enolo Wine Café

Find some of the best downtown wine deals at this chic spot that focuses on seasonal wines from a variety of regions around the globe. With a rotating menu of over 20 options to purchase by the glass, Enolo offers select wines from their menu for $7 a glass during their weekday happy hour from 4 to 6 pm Monday through Friday. Try the Grand Board of meats and cheeses accompanied by a wine from their select wine list. Make sure to enjoy their wine flight program as well, which changes seasonally and is usually thoughtfully curated to match Chicago’s everchanging seasons. 450 N. Clark St, 312.477.7674

Selena Fragassi
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