Address: 1640 N Damen Ave, Chicago, IL 60647

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For a nostalgic experience with the requisite hint of trendiness, Cans is the place to go. While canned beer – 27 varieties – is definitely the specialty, bottles and cocktails can also be had. Grab a seat at one of the two bars, or sink into delightfully deep booths; thanks to waitstaff bearing Palm Pilots, your suds...

Address: 140 E Walton Pl, Drake Hotel, Chicago, IL 60611

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This bar has become a Chicago landmark. It sports Prohibition-era decor, and low lighting sets the mood. The martini is the signature drink, and cabaret-style pianists and singers entertain nightly. The menu includes a number of items that come from the kitchen of the Drake's notable Cape Cod Room. Try the Bookbinder...

Address: 3741 N Southport Ave, Chicago, IL 60613

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A pressed tin ceiling and cozy booths lining one wall are just a few of the details that help Cullen's distinguish itself from Chicago's glut of Irish bars and restaurants. Folks come here to grab a bite to eat or simply to knock back a couple of pints. Shepherd's pie, burgers, and mac and cheese represent the edible...

Address: 440 W Randolph St, Chicago, IL 60601

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If it seems like Ghostbar popped off the pages of hip "Wallpaper*" magazine, that's because it did. The British publication paid homage to the streamlined club, a polished complement to downstairs' super-trendy N9NE restaurant. Get in the mood with a Ghostini cocktail (complete with Casper swizzle stick), and then sit...

Address: 5148 N Clark St, Chicago, IL 60640

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199 bottles of beer on the wall...and 30 drafts, too. How do you choose? Just ask one of the well-versed waitstaff, who can also recommend an entree to pair perfectly with your brew of choice. A somewhat smoky front room doesn't discourage locals and visitors from crowding in, but the spacious backroom invites...

Address: 1 Oak Pl, Chicago, IL 60611

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Enter through the alley, move past the beautiful blond hostess (having met the cover charge and dress code), descend the stairs, and be transported to a 10,000-square-foot subterranean speakeasy of the new millennium. Le Passage's funky decor and talented DJs spin you from dance floor to two great bars. Yow Bar, named...

Address: 1745 W Armitage Ave, Chicago, IL 60622

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Omnipresent 77-year-old Marie, the lounge's original owner and bartender, looks like your grandmother and acts like a truck driver. She runs the place, sings on occasion, does magic tricks, and for a shot of Jagermeister, she'll be your new friend. The place started as a polka joint in 1961, and although some original...

Address: 22 W Hubbard St, Chicago, IL 60611

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A trendy, high-concept space draws crowds nightly to this happening bar, lounge, and restaurant. The bustling front bar is the place to see and be seen. Sample a specialty cocktail, like the Rockit Root Beer – root beer, Stoli Vanil, and Godiva white chocolate liqueur – while you take in the scene. Looking for...

Address: 1471 N Milwaukee Ave, Chicago, IL 60622

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Educating patrons about "the world's most misunderstood spirit" is no small feat, and Salud takes its work seriously. More than 75 premium, 100%-agave tequilas are lovingly served in generous, two-ounce pours for your sipping pleasure. For dedicated tequila lovers, dinners and tasting sessions further the experience....

Address: 1240 N Wells St, Chicago, IL 60610

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One of Old Town's hippest nightspots, Spoon attracts a flurry of stylishly-clad beautiful people on a nightly basis. Come to this upscale restaurant/lounge for a terrific international dinner and an even better night of dancing and general merriment. DJs spin the hottest grooves until the wee hours at this trendy bar,...