Logan Square’s favorite wine bar, an influential and reputable establishment in the neighborhood and around the city, is celebrating 25 years this month.
To commemorate this momentous occasion, Webster’s has selected some unique, old wines and is offering one bottle for $25 to the first customer who requests it until Nov. 30 These handpicked wines are not only valued anywhere from $100 to $400, but some are rare and irreplaceable.
Webster’s opened its doors in 1994 when Janan Asfour and Tom McDonald left their jobs as litigation consultants and established Chicago’s first and only wine bar in Lincoln Park. When building Webster’s, Asfour and McDonald drew inspiration from a trip they had taken to Seville, Spain, though their passion for wine spans the globe. To this day, Webster’s wine selection is known for its range and diversity.

Since the beginning, Asfour and McDonald were determined to bringing great wine to Chicago. They focused on small, family-owned, environmentally conscious vintners and looked for wines with limited intervention. Their philosophy was, and is, “that what makes wine so special is that, when made with little to no manipulation (additives or chemicals), wine—way more than any other type of drink—can truly speak about a particular place.”
McDonald shared that he’s particularly proud of how impactful Webster’s has been on starting and growing the wine scene in Chicago.
“Some of our former employees went on to not only open their own wine bars but over the years, our former staff became sommeliers at places like Alinea, Parachute, and Giant,” McDonald said.
Former employees went on to open wine shops like Red & White and Rootstock, made award-winning wine-featured films, started their own wine import and distribution business, Jill Mott Selections, and more, he said.
“We are proud of that,” he said. “It’s amazing that we brought together so many talented people over the years who have gone on to do amazing things. It’s humbling.”
These success stories are a testament to how committed Asfour and McDonald are to the importance of learning about wines, their sources, and their histories. Part of this commitment involves taking their staff to a multitude of wine regions around the world, including vineyards in the U.S., Europe, and South America, to personally experience the region’s culture and identity. Their passion is infectious and it’s evident in the way their staff talk about the wines. If you ever ask for a recommendation, you’ll likely be met with some good insight and, if you’re lucky, a story or two from these travels.
Logan Square is fortunate to have so many domestic and international varieties of wine right in its backyard. Webster’s may have originally opened in Lincoln Park, but Logan Square has been its home since 2014. McDonald said that the move was a good one.
“We love the diversity of the neighborhood, the energetic vibe, and the talent and creativity of the residents,” he said.
In a neighborhood where new bars and restaurants are a dime a dozen, Webster’s is a timeless classic. So whether you’re in the mood in for an old favorite wine or on the hunt for something new and interesting, stop by and raise a glass to Webster’s and its 25 incredible years.
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