During his free time, the former Michelin-starred Elizabeth’s wine director and sommelier based in Chicago, Derrick Westbrook, would likely be expected to unwind in similar high-end locations.

Westbrook confesses that after several years of service in restaurants, he relishes the unique perspective of being a fine dining guest. Nonetheless, Westbrook does not usually patronize venues boasting extensive assortments of classified Bordeaux or high-end steakhouses with a specialty in cult Napa cabs, when he’s off-duty.

“I’m probably most apt to be having wine or beer at the Bronzeville Winery,” declares Westbrook. “My judgment may be slightly skewed because I developed the wine list there.” Westbrook, however, finds Bronzeville to be an inviting and jovial location where he loves to bring friends, who may or may not know anything about wine.

Westbrook states as a principle, “I have a preference for places that are subtly intelligent. Places that prioritize excellent food and beverages.” He finds himself attracted to bars and restaurants with wine lists that “are well-considered and selected by someone who genuinely understands and is passionate about wine.” He prefers places that don’t require discussions about appellations or classifications, he adds.

Bronzeville showcases a unique and intelligent collection of wines. You might not find Champagne, but you could discover Thierry Tissot’s 2018 extra-dry rosé, a méthode traditionelle sparkling mix of gamay and mondeuse from Bugey in eastern France. Instead of usual Cabernet Sauvignon from California or France, there’s a vintage 1995 Quinta do Poço do Lobo from Bairrada, Portugal. There are numerous wines, “that wouldn’t typically be poured elsewhere,” states the sommelier. These are unique or aged wines that need attentive staff to showcase them consistently. Many of the wines are offered by the glass or in affordably priced flights. It’s a location that invites exploration of new and distinctive wines without much investment.

The chance to uncover small, family-run producers who are not part of mainstream or industrial beverage production attracts industry experts. This is conveyed by Dila Lee, a sake and spirits manager in Chicago for Komé Collective, which imports premium Japanese beverages.

Lee, with years of restaurant management experience in Chicago and San Francisco, now spends most of her time traveling across the country visiting restaurant accounts. In her spare time, she’s attracted to places where the beverages “narrate the tale of their origin and the people who create them,” and where “the staff are truly enthused about them.”

For more than twenty years, Webster’s Wine Bar has been a reliable spot for Chicago’s wine and beverage industry, according to Lee. The cozy Logan Square venue, which moved from its original Lincoln Park location in 2014, “is an industry playground,” adds Westbrook. Webster’s Wine Bar is where sommeliers go to immerse themselves in their craft. However, it’s not famous for grand-cru Burgundy or grande-marque Champagne, instead, it’s known for wines like Louis-Antoine Luyt’s El Mismo from Chile’s Maule Valley, and J.B. Becker’s Wallufer Walkenberg Spätlese Riesling from the Rheingau, a graceful wine produced by one of Germany’s most elusive winemakers.

BYOB nights are a common occurrence when beverage professionals gather, as shared by Eduard Seitan, a renowned sommelier and associate of One Off Hospitality. One Off Hospitality runs nine prestigious eateries in Chicago such as avec and Publican Quality Meats.

Seitan has been hosting routine BYOB dinners at Four Seasons Dumplings located in Bridgeport for some time now. This venue is his favorite spot for entertaining visitors or hanging out with buddies. Despite the lack of an enchanting ambiance, the place offers delectable, authentic Chinese cuisine. He mentions that it’s an exceptional chance to share exquisite bottles with individuals who are knowledgeable and also love good quality wines. The cost usually doesn’t exceed $25, which includes a hefty tip. His only demand is that each guest must bring a bottle of natural wine.

Natural wines are unquestionably loved by beverage professionals in Chicago. Seitan mentions that many of them have championed this for two decades. The natural wine trend that originally emerged in cities like New York, Paris, and San Francisco finally made its way to Chicago. Seitan adores the exciting and delicate umami flavors he finds in natural wines. Additionally, the growing fondness for these wines coincides with the beverage industry’s increasing endorsement of regenerative farming practices and least interventionist production techniques.

For those who think the above is too overbearing, Westbrook suggests trying Easy Does It located in Logan Square. It’s a natural wine bar and lounge that puts great emphasis on fun. They hold an open-jam session every Monday, have a DJ booth, and a raw-bar pop-up on the patio on Sundays. “If you’re in search of something funky, they truly embrace that style” he quotes. “For me, it’s always a pleasure to sample an array of these wines and exercise 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.

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, bronzevillewinery.com

Easy Does It (Logan Square)

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

Four Seasons Dumplings (Bridgeport)

3205 S. Halsted St., 312-265-0568, 4seasonsdumpling.com

Jinsei Motto (West Loop)

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

Webster’s Wine Bar (Logan Square)

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

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, apoloniachicago.com

avec (River North)

Seitan, a father to a 2-year-old and a volunteer pilot for the charitable animal rescue organization Pilots N Paws, finds his evenings quieter than before. He spends his weekends indulging in brunch at his own dining place, avec River North, with his family and friends. He boasts of it as the city’s top brunch spot. Mimosas and bloody marys are a brunch favourite, yet Seitan also recommends avec’s unique and affordable wines; like the Portuguese red field blend, Casa de Mouraz’s Chibu, made with almost 20 different kinds of red and white grapes, or Tchotiashvilli Kisi, a Georgian orange wine which is fermented in qvevri, old amphorae.

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

Miru (Lakeshore East)

Miru is a Japanese restaurant located on the 11th floor of the St. Regis Chicago, opened last spring. It boasts a 12-seat marble sushi bar. Kat Hawkins, its wine director, is lauded for her meticulous pairing of wine with Japanese dishes. Lee shares that ensuring the wine acts as the best supporting actor to these dishes and flavors is a challenge considering the subtlety of fresh ingredients and deeply flavored umami components inherent to Japanese cuisine.

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

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, ninebarchicago.com

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, printersrowwine.com

Proxi (West Loop)

Proxi is a culinary tribute by Chef Andrew Zimmerman to the street foods he has encountered on his journey. The focus is particularly on Wine Director Alex Ring’s beverage menu characterized as “diverse yet tightly curated” which includes wine, craft cocktails, beer, and sake. This borderless cuisine provides an extraordinary chance to pair and experience a versatile range of unexpected flavor combinations.

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

Soif (Logan Square)

The “speakeasy-like wine bar” Soif, is hidden in a basement that can be accessed via an unmarked staircase in its sister restaurant, the Roman cucina Testaccio, as per Seitan. The wine list predominantly features French wines and is surprisingly affordable, emphasizing small producers and natural wines.

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

Anna Lee Iijima is a freelance writer.