Best cocktail bars in Chicago

The best cocktail bars serve everything from classic Manhattans to drinks in skulls

Photo: Jason Little
Grapefruit and Mint Gintonic at Sable

Cocktails have come a long way from the classic martini. Sure, we love a well-made classic, but in the past several years Chicago bartenders have been elevating mixed drinks to an art form. From a tiki bar to a molecular gastronomy lounge to a gin-focused joint, Chicago's best cocktail bars do it all. We wouldn't blame you if you wanted to visit every bar on the list—just don't do it all in one night.

RECOMMENDED: Best bars in Chicago

Best cocktail bars in Chicago

Analogue

Critics' pick

It's no surprise that this bar from a couple of Violet Hour vets has an excellent cocktail list. But besides the purls (bitter beer-based cocktails), airplane bottle shots and spins on classic drinks, Analogue also offers an outstanding Cajun menu from Alfredo Nogueira. The warm, flaky biscuits, fried chicken sandwich on toast and smoked fish dip are standouts, and together with the cocktails make this a low-key bar we want to hit every night of the week.

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Logan Square

The Aviary

Critics' pick

When Grant Achatz does a cocktail bar, it should go without saying that it's no ordinary cocktail bar. At the Aviary, which opened next door to Next in 2011, cocktails receive the same innovative treatment from beverage director Micah Melton as the food at Next or Alinea. That is to say, you should expect to drink cocktails like the Junglebird, a science experiment in liquid density, with layers of rum, campari, pineapple-lime syrup and rum "pearls" suspended in the drink. O'Doyle Rules comes with a fried banana snack on top of the rum-curry-cognac concoction, while Loaded to the Gunwalls is delivered with a single tapered candle. The drink, with pineapple, hazelnut and Batavia Arrack, is served in a glass ship in a bottle. You've never seen a drink like it, and given how rare a visit to the Aviary is, you may never again.

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West Loop

The Barrelhouse Flat

Critics' pick

You come to the Barrelhouse Flat for cocktails—it’s one of the finest drinking establishments in the city, thanks to head bartender Stephen Cole’s list of 70 classics that range from familiar (whiskey sour) to arcane (Jimmie Roosevelt, anyone?) and oft-changing house cocktails. But you stay at the Barrelhouse Flat for the food, namely the headcheese poutine and whatever the daily flavor of popcorn is.

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North Side

Berkshire Room

Berkshire Room, the bar in River North’s Acme Hotel, doesn't just name-check the Berkshire Hotel, the Acme’s former name from the 1920–1950s. The decor takes cues from old-world cocktail lounges and gives them a current, urban twist. The main bar area is set off by a mix of tall, white-washed walls and checkered tile flooring. Side rooms, off the main bar, include whiskey lockers for rare spirits, barrel-stave wall paneling, copper light fixtures and plush seating. And as for drinks, bartender Benjamin Schiller has a short list of original cocktails (Weston, with wheated bourbon, Dark Matter Coffee essence and pipe tobacco, is a new classic) plus a dealer's choice menu that always leads to exactly what you want to drink.

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River North

Bernard's Bar

Looking to go luxe? The Waldorf Astoria’s entryway alone is impressive. But sneak up the stairs to this covert cocktail lounge and you’ll feel outright special. Chairs are plush, lights are dim and—best of all—the classic cocktails are stellar. Oysters and charcuterie make their way over from the upstairs restaurant, Balsan. Our advice? Start there, then head up to Balsan’s bar for a proper burger and beer to wrap the night.

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Gold Coast

Billy Sunday

Critics' pick

Who would have guessed longtime Trotter's chef Matthias Merges would find his calling checking IDs at the door of a Logan Square bar? Granted, his is not just any bar: Here, barkeep Alex Bachman combines his penchant for unusual ingredients (a syrup made from maidenhair ferns, say) with an uncanny sense of balance, turning out creations that both pay homage to and defy tradition—often simultaneously. Though Billy Sunday is squarely a bar, the food is a worthy companion to the drinks: Don't miss any of the snacks in jars.

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Logan Square

The Drifter

Critics' pick

Located under the Green Door Tavern, the Drifter is a cozy bar from Liz Pearce (Gage, Drawing Room, Aviary), who serves up a rotating selection of cocktails (printed on a tarot card menu). Your order depends on which cards she deals each night, so keep your fingers crossed for the velvety chocolate negroni or South American Mistress, a smooth blend of pisco, vermouth and Fernet, balanced with chocolate liqueur and blackstrap bitters. The space is a former speakeasy and much of the original decor remains; the occasional performances, like a belly dancer, feel right at home amidst the vintage vibe.

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River North

Drumbar

The gorgeous 18th-floor bar of the Raffaello Hotel boasts three prime sections: a handsome, dim interior full of tufted leather banquettes; a chic exterior deck lounge with open fire pits; and (our favorite) a narrow indoor-outdoor corridor where the marble floor and arched windows play against contemporary green stools. Bartending team Whitney Morrow, Gary Matthews and Marko Tomovic are serving a lot of classics, but their own drinks, like the Point Break, with tequila, mezcal, citrus and chocolate liqueur.

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Magnificent Mile

Lost Lake

Critics' pick

The tiki revival continues with Lost Lake, a new spot from Paul McGee (Three Dots and a Dash) that opened in January 2015. The core components of the tiki style are here—drinks that double as flower arrangements, lush tropical decor, Hawaiian print–clad bartenders and Americanized Chinese snacks—but the drinks are more challenging (and interesting) than you find at most tiki bars. Hula Hips of Heaven has a double dose of agave, with smoky mezcal and tequila providing a strong base for citrus fruits and spices, while the Scotch-based Cocoanut Grove Cooler has a punch of peat smoothed out with pineapple and lemon, plus Batavia Arrack, rum’s Indonesian predecessor. Thank heaven for Thank You, the adjacent take-out spot, because you'll need the salty, greasy snacks like egg rolls and chicken wings to keep you standing upright.

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Avondale

Sable Kitchen & Bar

Critics' pick

Although esteemed bartender Mike Ryan exited Sable in 2015, John Stanton picked right up where he left off. The cocktail list is expansive, but expect excellent takes on the classics, plus balanced and complex originals, like War of the Roses. The Spanish gintonic menu, which offers tonic-heavy gin and tonics that change with the seasons, is worth exploring, no matter the weather outside.

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River North

Scofflaw

Critics' pick

Veterans of the Whistler and Boiler Room joined together to open this bar. One of the two rooms here looks a lot like the Violet Hour, which makes sense since cocktails (specifically gin cocktails) are a focus of the place, like the Special Sweater, made with Scofflaw Old Tom gin, vermouth, spiced coffee liqueur and lemon. The other room is less loungey and truer to what Scofflaw is, which is a top-notch, friendly neighborhood joint.

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Logan Square

Three Dots and a Dash

The lushly decorated tiki bar that jumpstarted Chicago's tiki craze opened in 2013 and serves beautifully garnished cocktails, with orchids, marigolds and pansies peeking out of skull, coconut and tiki head glasses. And they’re potent—the classic Jet Pilot has three types of rum, plus absinthe, citrus and spices—which makes bar snacks like spicy Thai fried chicken a must order.

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River North

The Violet Hour

Critics' pick

This hip cocktail lounge is exactly what you’d expect from a bar named after a line of T.S. Eliot poetry: pristine (the carefully constructed cocktails, like the aquavit-based Coattails, are excellent), pretentious (you won’t find a sign on the door—just look for the long lines) and, ultimately, completely and unarguably gorgeous.

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Wicker Park

Weegee’s Lounge

Critics' pick

Ten years from now, when this strip of Armitage is populated with coffee shops and vintage clothing stores, this old-school, soul record–playing, classic cocktail–mixing bar will be overrun with hipsters vying for their turn in the photo booth. Start hanging out here now so you can say you knew it in the good old days.

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Logan Square

The Whistler

Critics' pick

From the outside, this place looks like a gallery (which, technically, it partially is). On the inside, it’s open and loftlike, with a permanent stage set up for weekly live music and performance. But behind the bar, the drink-slingers have perfected the art of the cocktail, skillfully crafting colorful refreshments that pack a punch. One sip and there’s no doubt that despite everything else going on here, the drinks are the reason to stick around.

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Logan Square

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