What are the best wine bars in Chicago?

Answers from Our Experts (1)

Lauren Viera

Among the handful of venues whose establishments fostered the popularity of the Logan Square neighborhood is Telegraph, an elegant wine bar facing the hip neighborhood’s monument roundabout. The full menu allows for a glorious sit-down dinner, but I’m just as happy to plant myself on a stool in the large bar area for a few rounds of wine and oysters.

The elder sister to Telegraph is Webster’s Wine Bar, managed by the same owners and seen as one of the city’s original go-to wine bars. Opened nearly two decades ago, Webster’s is located in a quieter corner of Lincoln Park near Ranch Triangle, perfect for a destination date-night, but also offers plenty of education programming for the oeno-curious.

Another well-established wine bar is The Tasting Room, located on the far west end of the popular Randolph Street Restaurant Row district. Celebrating a decade of pours, this local favorite is a comfortable two-story destination that caters to both wine-and-cheese outings and sit-down meals.

Newer to the scene is The Boarding House, the massive three-story restaurant, wine bar and lounge opened by Master Sommelier Alpana Singh. Located in an historic late-19th century former boarding house, the full-service restaurant features a wine book several hundred deep—including a rotating selection of recommendations for those who’d rather not read the entire tome.

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