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Best cocktail bars in Chicago

The best cocktail bars in the city serve everything from classic Manhattans to flaming 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

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

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

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

Billy Sunday

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 Broken Shaker

The Chicago outpost of Gabe Orta and Elad Zvi’s much-lauded Miami cocktail bar is located in the Freehand Hotel and serves some of the city's most interesting cocktails. Try a Garrett's Popcorn–inspired old-fashioned, Chicago-style hot dog margarita or more straightforward drinks, like a sherry cobbler on draft. The bar is tiny, but seats are also available by the fireplace in the lobby, and it's a cozy spot to spend the colder months.

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River North

The Drifter

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

GreenRiver

When restaurateur Danny Meyer and New York’s Dead Rabbit Grocery & Grog team up to open a cocktail bar, it's a big deal. Even bigger: when that bar is on a rooftop in Chicago and Julia Momose (Aviary and Office) is making the drinks. Named for historical Chicago figures, the drinks incorporate unexpected ingredients, like herbal Old Bay tincture in the mezcal-based Diamond Jim. Food from Aaron Lirette rounds out the experience, and the uni spaghetti is a must-order.

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Streeterville

The Heavy Feather

We weren't around to bar hop through the '70s, but we're pretty sure the drinks were not quite as good as Heavy Feather bartender Doug Phillips (Scofflaw) makes them seem. At the sleek fern bar, Phillips brings back cocktails from the era and greatly improves upon them. A brand new cocktail list just launched, with a Tom & Jerry, Brandy Alexander and Mudslide ice cream drink, and we can't wait to explore the new options.

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Logan Square
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Comments

1 comments
KC D
KC D

Check out the hiiden gem that isNeat Kitchen+Bar in westmont when you do the list for Best Whiskey Bars.  They should also be on the list for beer, cocktail, and wine bar.  Check it out.  It will not be a secret for much longer.