Chicago Cocktail Bars
10 Spots Reinventing the Nightcap

A lot has changed behind the bar since Jerry P. Thomas published The Bon Vivant’s Companion in 1862, which happens to be the first American cocktail book. Still, there remains a constant: the possibilities of what can be mixed into a glass are nearly as varied as people’s tastes. Today, Chicago remains home to a number of renowned cocktailing hotspots, some of which attempt to redefine the craft in search of evasive newness, while others that wield Hawthorne strainers to dig deep and tap a rich vein of tradition.
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Logan Square: Sippin’ on More Than Gin and Juice

This Logan Square gin joint mixes one part Chicago speakeasy and one part London lounge. Still, under its baroque veneer, Scofflaw remains a friendly neighborhood spot that offers tasty small plates and hands out free fresh-baked chocolate-chip cookies at midnight.


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River North: Cocktails Garnished with History

Second-story River North lounge features upscale ‘60s décor and a menu of classic cocktails that includes informative anecdotes about each drink’s history. For example, it claims that the French 75 was created when British WWI soldiers in France tried to make a Tom Collins, substituted difficult-to-find club soda for champagne, and named it for the French 75mm field gun.


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West Town: Molecular Gastrobooze

At The Aviary, “the drinks are striving for a from-the-ground-up perfection,” reveals the Wall Street Journal. As much should be expected from Grant Achatz, the world-renowned culinary talent who masterminded this envelope-pushing cocktail experience. The attention to detail is seen throughout: nearly 20 varieties of ice are used to craft drinks that are served in light-bulb-shaped glasses and smoke-filled bags.


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Wicker Park: Upscale Speakeasy

Its name lifted from a passage in T.S. Eliot’s The Waste Land, The Violet Hour offers a charming vintage drinking experience. After stepping through the “secret” front door, visitors find a gorgeously decorated speakeasy that can make them feel as if they’ve traveled back in time. Standing around or using cell phones is not allowed, and conversations flow freely over the hushed music.


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Logan Square: Budget Craft Cocktails

Expertly crafted yet reasonably priced cocktails are the focus at the Whistler, an inviting neighborhood spot that GQ named one of The Best 25 Cocktail Bars in America. It may take a minute or two to grab a drink from the meticulous bartenders, but the dim lighting and live music add to a memorably relaxed vibe. It’s one of the few live music venues in the city that never charges a cover.


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River West: Cozy Drinking

Bartenders at this no-nonsense cocktail spot make ‘em stiff and simple. The bar just may be the smallest in town—it measures 3.5 feet wide at its narrowest section and 15 feet wide at its roomiest. Still, loyal patrons happily squeeze in and order up a perfectly prepared Manhattan or margarita.


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Near North: Massive Spirits Menu

This new-American gastro-lounge also happens to whip up classic cocktails made with local ingredients. Its massive 40-foot bar is one of the largest in the city, and is a great spot from which one can admire the establishment’s modern take on ‘40s décor or peruse the head-spinning, 30-page spirits menu.


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Gold Coast: Innovative Drinks and Contemporary Eats

Named one of The Best Bars in America in 2011 by Esquire, The Drawing Room attracts dressed-up Rush St. revelers with fantastic cocktails and elegant touches such as velvet-lined chairs. Patrons can also sample seasonal, progressive American dishes such as foie gras parfait and steak tartare with marrow mustard.


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Wrightwood Neighbors: Late-Night Luxury

This two-story cocktail den is perfect for kicking back in a leather button-tufted sofa seat while sipping on a classic cocktail and warming up next to the fireplace. Around 70 classic cocktails populate the extensive drink menu, and visitors can also order up tasty bites such as deviled eggs or shoot pool on a beautiful table until the 4 a.m. closing time.


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West Town: Hidden-Away Gem

Its name meaning “bar in the city” in French, Bar DeVille may not catch the eye of passersby with its rough exterior, but definitely charms with an interior that gives off a European parlor vibe. Head mixologist Brad Bolt crafts cocktails that range from classic to specialty as visitors dance it out in the rear lounge or shoot pool in an antler-ornamented room.


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