The Great Chicago Wine Bar Search: After 18 Years, Webster's Is Still Pouring Good Times

The Great Chicago Wine Bar Search: After 18 Years, Webster's Is Still Pouring Good Times

Finally, after a year of great wine bar searches my journey leads me to the “granddaddy of them all” Webster’s Wine Bar (1480 W Webster Ave), while  trendy wine establishments come and go, this north side staple has been here since 1994.  It is by far Chicago’s oldest and has become the place when Chicago learns about wine.  Webster’s serves more than 40 wines by the glass and over 500 reserve wines from around the world focusing on artisanal and family-owned wineries.  They also serve a selection of fine beers and spirits and offer a variety of small plates, artisanal cheeses and regional dishes specifically chosen to complement the wine selection. Websters also features live music on Mondays, as well as  a variety of tastings .

When I spoke with owner Janan Asfour about the secret of their longevity in what’s becoming a crowded market, she told me: “From the beginning, we have aimed to share our passion for wine by offering classes and wine tastings for beginners and “experts” alike. Our goal, quite simply, is to provide high-quality, hand-crafted, unique wines in a comfortable, casual, and unpretentious setting and to spread the joys of fine wine. With our fantastic staff, we’ve traveled to many of the major wine-producing regions of the world including the United States, Spain, Greece, Italy, Germany, Austria and France and are always humbled and amazed by each place’s distinct culture, cuisine, and methods of wine-making. We love to bring home our stories, discoveries, and photos and share them with our friends and customers. It’s been over 18 years since we opened, and although we’ve grown significantly, we still strive to maintain a comfortable and relaxing atmosphere where everyone can enjoy a great glass of wine and escape the stress of daily life.”


We will be hosting a Sunday “Winedown” at Webster’s Dec. 2nd Space is limited so you must RSVP

Champagne Tasting 12/5

Scotch  Tasting   12/19

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