Chicago’s best wine destinations, according to the experts

On his nights off, you might expect to find Derrick Westbrook, the Chicago wine director and sommelier, formerly of the Michelin-starred Elizabeth in Lincoln Square, unwinding in similarly gilded hot spots.

After years of working restaurant floors, Westbrook admits he enjoys fine dining from the unique lens of a guest. But when Westbrook is off the clock, he’s not known to frequent spots boasting deep collections of classified Bordeaux or upscale steakhouses specializing in cult Napa cabs.

“Honestly, you’re most likely to find me having wine or beer at the Bronzeville Winery,” Westbrook says. “I’m a little biased because I built the wine list there.” But Bronzeville is the kind of open, convivial place where Westbrook likes to bring friends, whether they know anything about wine or not.

As a rule, “I like places that are sneaky-smart. Places that lead with great food and drinks,” Westbrook explains. He’s drawn to restaurants and bars where “the wine lists are thoughtful and curated by someone who really knows and cares about wine,” but don’t necessitate lectures about appellations or classifications, he says.

Bronzeville’s selection of wines is indeed both sneaky and smart — rather than Champagne, you might be guided to Thierry Tissot’s 2018 extra-dry rosé, a méthode traditionelle sparkling blend of gamay and mondeuse made in Bugey in eastern France. Instead of cabernet sauvignon from California or France, you’ll find a well-aged 1995 vintage Quinta do Poço do Lobo from Bairrada, Portugal. There are “a lot of wines that wouldn’t make sense to pour anywhere else,” he says, wines off the beaten path, or “older wines that are too delicate or too expensive to pour unless you have staff who can make sure they’re being shown consistently.” Much of the list is available by-the-glass or packaged in accessibly priced flights. It’s a place that requires little commitment to explore new and unusual wines.

Opportunities to discover small, family-owned producers off the beaten path of conventional or industrial beverage production are a big draw for industry folk, explains Dila Lee, a sake and spirits manager in Chicago for Komé Collective, an importer of premium Japanese beverages.

Lee spent years managing restaurants in Chicago and San Francisco before pivoting to sales. She spends much of her time traveling across the country visiting restaurant accounts. On her own time, she’s drawn to places where the beverages “tell a story about the places they’re from and the people who make them,” and where “staff are really passionate about them.”

For over two decades, Webster’s Wine Bar has been a trusted watering hole for Chicago’s wine and beverage trade, Lee says. The snug Logan Square venue (it relocated from its original Lincoln Park venue in 2014), “just lends itself to being an industry playground,” Westbrook adds. “It’s where all the somms go when they really want to geek out.” Not necessarily on grand-cru Burgundy or grande-marque Champagne, he says, but on things like the Burgundian Louis-Antoine Luyt’s El Mismo, a spry, perfumed red sourced from 200-year-old vines of pais grapes in Chile’s Maule Valley. Or J.B. Becker’s Wallufer Walkenberg Spätlese Riesling from the Rheingau, a sinewy, delicate wine made by one of Germany’s most elusive winemakers.

Tom Bennett pours sparkling wine as Heidi Pratt, left, and Shannon Grant sit at the bar at Webster’s Wine Bar, 2601 N. Milwaukee Ave., on March 22, 2024, in Chicago. (John J. Kim/Chicago Tribune)

When beverage professionals go out together, BYOB nights are an industry mainstay, explains Eduard Seitan, a sommelier and partner of One Off Hospitality, which operates nine Chicago restaurants including the avec and Publican Quality Meats.

For years, Seitan has organized regular BYOB dinners at Four Seasons Dumplings in the Bridgeport neighborhood. It’s his go-to venue, whether he’s entertaining visiting winemakers or his friends. “There’s not a whole lot of ambiance, but it’s just really good, honest Chinese food,” he says. Moreover, it’s an opportunity to share special bottles with friends and colleagues most likely to appreciate them, often for less than $25 including a very generous tip, says Seitan. His only requirement is that “everyone has to bring a bottle and it has to be natural.”

The pull of natural wines among beverage professionals in Chicago is unquestionable. “A lot of us have been pushing this for 20 years already,” says Seitan. “That movement you saw in cities like New York or Paris or San Francisco, that wave finally reached us in Chicago.” Seitan says he embraces the liveliness and subtle umami he senses in these wines, but the popularity of natural wines also aligns with increasing support by beverage industry professionals for regenerative farming practices and minimally interventionist production methods.

A selection of wines are on display for sale at Easy Does It, 2354 N. Milwaukee Ave., March 22, 2024, in Chicago. (John J. Kim/Chicago Tribune)
A selection of wines are on display for sale at Easy Does It, 2354 N. Milwaukee Ave., on March 22, 2024, in Chicago. (John J. Kim/Chicago Tribune)

If all that sounds too preachy, Westbrook recommends Easy Does It in Logan Square, a natural wine bar and lounge that’s high on the fun factor. Every Monday features a live open-jam session, there’s a DJ booth and a raw-bar pop-up on the patio on Sundays. “If you’re looking for some funky stuff, they really lean into that style,” he says. “For me, it’s always great to taste through these kinds of wine and really work that part of my brain.”

Easy Does It also serves an excellent selection of beer, cider, kombucha and cocktails. “Chicago’s dining scene has grown so much in the past decade,” says Lee. “It’s not just about really cool wine lists, but craft cocktails and beer, spirits and sake, too, but all done really well,” she says.

Victoria Homza and Pace Nalbone, both of Pittsburgh, eat from the omakase menu and drink sake at Jinsei Motto, the sushi bar and izakaya on W. Randolph Street in Chicago, on March 22, 2024. (Terrence Antonio James/Chicago Tribune)
Victoria Homza and Pace Nalbone, both of Pittsburgh, eat from the omakase menu and drink sake at Jinsei Motto, the sushi bar and izakaya on West Randolph Street in Chicago, on March 22, 2024. (Terrence Antonio James/Chicago Tribune)

As a sake specialist, Lee favors Jinsei Motto, the sushi bar and izakaya housed in the CH Distillery (home to the Chicago icon, Jeppson’s Malört). Located in the West Loop, “it’s the largest by-the-glass sake program in Chicago by far,” says Lee, but more importantly, it’s a place where the list is “dynamic and constantly evolving,” a rare chance in America to catch up on the latest sake trends from Japan.

Bronzeville Winery (Bronzeville)

4420 S. Cottage Grove Ave., 872-244-7065,

Lead bartender Emmentt Jackson finishes pouring a wine flight during happy hour at Bronzeville Winery, 4420 S. Cottage Grove Ave., May 17, 2023, in Chicago. (John J. Kim/Chicago Tribune)
Lead bartender Emmentt Jackson finishes pouring a wine flight during happy hour at Bronzeville Winery, 4420 S. Cottage Grove Ave., on May 17, 2023. (John J. Kim/Chicago Tribune)

Easy Does It (Logan Square)

2354 N. Milwaukee Ave., 773-420-9463,

Four Seasons Dumplings (Bridgeport)

3205 S. Halsted St., 312-265-0568,

Jinsei Motto (West Loop)

564 W. Randolph St., 312-884-9602,

Webster’s Wine Bar (Logan Square)

2601 N. Milwaukee Ave., 773-292-9463,

More go-to spots from Chicago’s top beverage professionals:

Apolonia (South Loop)

Apolonia is South Loop’s popular Mediterranean restaurant. Lee describes wine director Jelena Prodan’s wine list as “an open box” of these “extraordinary, hidden gems in the wine world.” There’s a vast selection of wines by the glass, “both classic and nouveau regions, in all kinds of styles and different producers” so “there’s something for everyone, wine nerds, the natty orange-wine crowd or even the fine-wine snobs,” Lee says.

2201 S. Michigan Ave., 312 363 2431,

avec (River North)

With a 2-year-old daughter and a volunteer gig as a pilot for the nonprofit animal rescue organization Pilots N Paws, Seitan doesn’t go out in the evenings as much as he used to. On the weekends, he enjoys brunch with family and friends at one of his own establishments, avec River North. “It’s the best brunch in the city, bar none,” he says. Mimosas and bloody marys are popular at brunch, of course, but Seitan loves avec’s selection of unusual and accessibly priced wines; the Casa de Mouraz’s Chibu, a Portuguese red field blend made from nearly 20 different red and white grape varieties, or the Tchotiashvilli Kisi, a Georgian orange wine fermented in qvevri, or ancient amphorae, for example.

141 W. Erie St., 312-736-1778,

Miru (Lakeshore East)

Miru, which opened last spring on the 11th floor of the St. Regis Chicago is a Japanese spot featuring a 12-seat marble sushi bar. Its wine director, Kat Hawkins, “takes so much care and attention in pairing wine with Japanese food,” says Lee. Japanese cuisine is so rooted in the delicacy of the freshest ingredients, or deeply flavored umami components, Lee explains, it’s a difficult task to ensure that “wine acts as the best supporting actor to these dishes and flavors.”

401 E. Wacker Drive, 312-725-7811,

Nine Bar (Chinatown)

Seitan loves this craft cocktail bar hidden behind the Chinatown mainstay Moon Palace Express. Lily Wang and her partner, Joe Briglio, run the second-generation enterprise, which her parents ran for over 30 years. It’s the kind of place where “everything about their cocktails just feels perfect, where sweetness and acidity, everything is just in balance,” Seitan says.

216 W. Cermak Rd., 312-225-4081,

Printers Row Wine Shop (South Loop)

A neighborhood wine shop since 2004, Printers Row is also a beer and wine bar specializing in low-intervention wines, unique spirits and local craft beer. “It’s one of the places I recommend the most,” says Westbrook. “The wine list is really cool, it’s unpretentious and homey, but you’re going to find really dope stuff,” including some “unique wines from Central and Eastern Europe that I love.”

719 S. Dearborn St., 312-663-9314,

Proxi (West Loop)

Proxi is chef Andrew Zimmerman’s ode to street foods encountered on his travels, but Lee pays particular homage to wine director Alex Ring’s “diverse yet tightly curated” beverage menu of wine, craft cocktails, beer and sake. The borderless cuisine “offers an amazing opportunity to pair and experience a wide range of unexpected flavor combinations there,” she says.

565 W Randolph St., 312-466-1950,

Soif (Logan Square)

This “speakeasy-like wine bar” is tucked away in a basement accessed through an unmarked staircase in its sister restaurant, the Roman cucina Testaccio, says Seitan. The wine list is predominantly French and surprisingly reasonable in price, with a focus on small producers and natural wines.

2456 N. California Ave., 773-895-6558,

Anna Lee Iijima is a freelance writer.

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