Best cocktail bars in Chicago

Looking for the best cocktails in town? Head to one of these spots.

Photograph: Christian Seel
Insane In The Membrillo at The Aviary.

Cocktails have come a long way from the classic martini. Sure, we love some gin, vermouth and bitters served in a martini glass, but in the past several years Chicago bartenders have been elevating mixed drinks to an art form. From a tiki bar to a gin-focused joint, Chicago has it all and we wouldn't blame you if you wanted to visit every bar on the list—just don't do it all in one night.

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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

The question Grant Achatz's cocktail lounge poses—intentionally or not—is: When a cocktail is an intellectual exercise, how much does it matter how it tastes? Some of these drinks are exhilarating for their presentation (the Rooibos, a hot cocktail served in a vacuum-pot coffee brewer), and some, like the Buttered Popcorn, are remarkable for their flavor (yes, it really does taste like popcorn). And sure, some are like the Blueberry, a pitcher of macerated spirits that changes the longer it sits, and are remarkable in every way. But whatever strengths the individual cocktails here exhibit, the outcome after drinking them is always them same: You'll never think of a cocktail the same way 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 from the Fifty/50 Restaurant Group (Greg Mohr and Scott Weiner) 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 offers "a very progressive beverage program while embracing old-school service standards."

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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—cocktails are stellar. Arsenic & Old Lace employs fresh tarragon to brighten up the anise in the pastis and, somehow, the pine in the gin, while yellow Chartreuse and sherry combine to mellow the bite of rye in the Witch & the Warlock. Oysters and crudo make their way over from the raw bar at 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 the banana pudding.

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Logan Square

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. Sable veteran Alex Renshaw took over the bar program from Craig Schoettler, and he's focusing on a large slate of classic cocktails.

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Magnificent Mile

Sable Kitchen & Bar

Critics' pick

The menu at this slick hotel spot is derivative of the gastropubby restaurants of the past decade: It’s got “flatbreads,” and various incarnations of the slider, and the perennially popular bacon-wrapped date. But it’s also got fantastic cocktails (even a drink called War of the Roses is balanced and complex). As mere companions to the cocktails, those sliders are better than fine; ditto for those pizzas. So think of Sable as a Bar & Kitchen and not the other way around.

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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. 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

Critics' pick

You won’t realize how much you were missing perfectly made tiki drinks in your life until you have one here. Since Trader Vic’s closed in 2011, there hasn’t been a dedicated tiki bar in the city, and we’ve needed one. The drinks are beautifully garnished, with orchids, marigolds and pansies peeking out of skull, coconut and tiki head glasses. And they’re potent.

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River North

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