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© The Chicago Bar Project   Written by Sean Parnell

Webster's Wine Bar

1480 W. Webster Ave. (2200N, 1500W)
Chicago, IL 60614
(773) 868-0608

"In Vino Est Veritas"

Webster's Wine Bar is the oldest and, in our humble opinion, the best wine bar in Chicago. Many others have come and gone since the husband-and-wife team of Tom MacDonald and Janan Asfour, self-described "burned-out litigation consultants looking for a lifestyle change," opened their wine bar in November 1994, replacing the Robert Henry Adams Fine Art gallery. This came ahead of a trend that has led to many more wine bar openings over the past 15 years. The couple's inspiration: a dusty old wine bar near the cathedral in Seville, Spain. Today, theater-goers from Webster Place across the street and other North Siders have found a great place to celebrate, impress a date, have a girls' night out, or otherwise sample wines from all over the world. Throw in a menu of small plates, complimentary music on Monday nights and even a ghost story stemming from the building's lurid past, and you can see why Webster's Wine Bar has "legs."

At the extreme west end of Lincoln Park, where this posh neighborhood meets the Chicago River, is where you'll find your oasis of vino. Webster's Wine Bar is located at the northeast corner of Webster Avenue and Dominick Street, within a three-story, red-brick building and across from the Webster Place 11 (purchased by Kerasotes in 2006 from AMC), making it the perfect location for the pre- and post-film drinks (free parking is available behind the movie theater, if you can find a spot). A humble wooden sign advertises the bar over the door, while a massive Stella Artois ad somewhat less humbly advertises the brew on the building's western wall.

Step through the door and you will find a lively, yet intimate candle-lit space with hardwood floors, a few scarlet Victorian couches, eclectic artwork, and burgundy walls. In the front room, the most sought after tables of the low-slung wooden variety lie in front of thick velvet drapes that hang over windows overlooking Webster. A wooden bar with ornate copper plating along its base straddles the front and back rooms and is a hive of activity, particularly with older singles eyeing incoming talent. The back room features more tables and an impressive stock of wine displayed on the north wall's wooden shelving.

Webster's Wine Bar offers an impressive 500 bottles of wine with 30 literally on tap for enjoyment by the glass, rotating regularly. Several flights, grouped by geographic region, are also featured as are monthly wine tastings—a wine experience worthy of both erstwhile swiller and oenophile alike. If you're interested in the wine tastings, make sure you get on the mailing list or check their website often because tickets sell out very quickly (priced $30-$40), particularly for tastings of champagne (annually in December) or any type of red. The staff is knowledgeable and courteous, especially the bartenders. A leather-bound menu illustrates the availability of appetizers & tapas (under $10), cheese plates, gourmet pizzas ($11), "regional specialty" entrées (most under $15), and desserts (under $10), all of which are offered by something less than a full kitchen. If you're really hungry, I recommend heading to Pequod's Pizza around the corner on Clybourn for some authentic Chicago deep dish. A few beers are available in bottles at Webster's, but why are you drinking beer here anyway? On my last visit, Stella Artois had been replaced with Jever, no matter what the huge sign says outside...

The main room is fairly small and crowded on weekends, so additional seating upstairs handles overflow in addition to the wine tastings and private parties for up to 100 people. The upstairs lounge sports a fireplace, sage-colored walls, couches, and long tables for groups. This space hosts the 2nd Story storytelling group every month, presented by the Serendipity Theatre Collective for $10. The staff also claims the second floor is haunted… employees have heard footsteps and a male apparition has been seen in what once served as a brothel many years ago in this 120 year-old building (à la Southport Lanes and Subterranean). If that weren't enough for you, the soulful Sticky Lupree plays free every Monday night and a sidewalk café with about ten tables is pleasant in summer, though there's not much to look at other than your date (hopefully).

Webster's is Chicago's oldest wine bar, and a worthy torch-bearer for a tradition that began in 1979 by the city's first wine bar, the now-defunct Le Bastille at 21 W. Superior. As you would guess, the comfortable and relaxing atmosphere draws somewhat of an older crowd (30s to middle-agers), though an affluent younger clientele filters in late. If you like neighborhood wine bars, be sure to check out Joie de Vin (Andersonville), Enoteca Roma (Wicker Park), DOC Wine Bar (Lincoln Park), and Bluebird (Bucktown)—the latter of which is under the same ownership as Webster's. Other Near North wine bars include Juicy Wine Co., Bin 36, 404 Wine Bar, and Third Coast Café & Wine Bar. If you feel like some music afterwards, head a block east on Webster to Green Dolphin Street for jazz on Monday & Tuesday nights, though you have been warned: Webster's Wine Bar is a place to go for a glass but expect to leave after a few bottles... For more information, check out the Webster's Wine Bar website. Salud!

"In Wine There Is Truth"

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