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Best Chicago Wine Bars

By Greg Wahl

Wine bars have evolved quite a bit in recent years, and now appear in a lot more varieties than they used to. You don't have to be a glasses-and-turtleneck Wine Spectator subscriber to appreciate them, either, as the food (and, yes, beer) at many local establishments has broadened the wine bar appeal. Menus that used to be limited to snack portions of cheese, crackers & charcuterie now compete with some of the best restaurants in town, and the pretense and snobbery that were often associated with the oenophile lifestyle have largely faded from the scene. At the very least, the wine bar is still hard to beat as a date destination. If you've generally avoided wine bars in the past, or are looking for new places to check out, here's a selection of the city's best destinations for savoring the grape.


The Francesca folks have done a good job capturing the old world wine cellar vibe at DiSotto Enoteca. Located, downstairs from Francesca's on Chestnut, this place is like a grotto of the grape. Just a block off the Mag Mile, it's also a welcome escape from the shopping action, and an ideal spot for post-theater lounging after shows at the nearby Broadway Playhouse.


Just down a few doors down from the notoriously rowdy Wiener's Circle is a cozy venue that occupies the opposite end of the dignity spectrum, D.O.C. Wine Bar. Relaxation is the key here, with cushy seating, a fireplace and a semi-private back room for more intimate gatherings. The bar is conveniently attached to Dunlay's on Clark for after dinner wine flights and lounging without the need for a neighborhood pub crawl. Note to West Suburbanites: D.O.C. also has a location in Lombard.


Located on the Tree Studios block (also home to the culinary real estate of Rick Bayless), Pops is a sophisticated hangout that offers the duality of a contemporary lounge in the main bar and a darker, cozier space downstairs. The venue is well-suited for private events, and is a popular starting point for bachelorette parties. Stop in for cover-free live jazz performances Sunday Tuesday.


Many passers-by only notice Café Bernard at this address, but downstairs is a real gem of a restaurant/wine bar that has been on this Lincoln Park corner for years. While Red Rooster lacks the polish that most LP-ers are accustomed to, it has plenty of character to offset the cool sophistication that tends to be prevalent among the area wine bars. It's pretty much like a French version of a rural pub. Also, since Café Bernard is currently closed for renovation, the choice between the two doors is a bit easier for the time being. Expect to find reasonable prices and really good mussels.


From the outside of the CME Building, one wouldn't readily expect to find an earthy hideaway like Rittergut inside. The ambiance is abundant, with river views and late afternoon sunsets along the riverside patio. The owners of neighboring restaurant/happy hour hangout Rivers have created something special in the business district, with a location that is especially appropriate for evening opera-goers attending performances at the Lyric across the street. For a co-worker gathering alternative, a private bar is available for group tasting events.


Aside from this establishment staking out new wine bar territory in Humboldt Park, it is also unique among the others in that the beer and food offerings are given roughly as equal weight as the wine selection. The ownership has the solid pedigree of a trio former Webster Wine Bar employees, so guests can expect good things. The chicken liver pate is among the many favorites that compels return visits among Rootstock's growing legion of foodies and oenophiles. Do expect a bit of a wait during prime seating times, though, as space is rather limited.


The Tasting Room location is a little challenging at night cab-wise, as it is situated near the end of the Randolph Street restaurant row, but the interior has much to offer, including skyline views, comfy couches, the "library" room, fondue, and, of course, lots of wine. West Loopers with a few bucks to spend on neighborhood leisure time, or anyone looking for an atmospheric hangout after a nearby dinner or United Center event, will find a lot to like here.


A recent addition to the scene, Vera puts a Spanish twist on the local wine bar experience. Elizabeth and Mark Mendez team up as Sommelier and Executive Chef, respectively, to present a seasonal wine list and generously-portioned (and reasonably priced) sharable plates, with an emphasis on Spanish hospitality. Tasting events are planned monthly; check the website for updates.


Having opened in 1994, Webster's Wine Bar is among the pioneers of the contemporary wine bar scene (they claim to be the city's oldest). Located at the far pedestrian edge of Webster St. in Lincoln Park past Clybourn, the bar is slightly off the beaten path, but the interior is a welcoming bi-level den of calm and candlelight with very little pretense. The selection is plentiful, with over 40 wines available by the glass and over 500 bottle varieties, as well as a small plates menu. Webster's at this point should be considered a Chicago neighborhood classic. Upcoming tasting events include a sampling of rare, artisanal Italian wines on March 14.

Greg Wahl is really not the guy with a pencil mustache and black beret in the corner at the Red Rooster. Really.
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