Food & Drink

The Best Cocktail Bars in Chicago

Published On 12/05/2013 Published On 12/05/2013
Sparrow Chicago
Nicholas James

The Berkshire Room

River North

With its cloud-scraping ceiling and checkered Alice in Wonderland floor, this boutique-hotel bar seems much bigger than it really is. Yet, once you take a peek around, the bar feels quite comfy, and the cocktails here have a similar ability to defy one’s expectations. Sure, you’ll find a nice selection of local spirits and inventive drinks, but the real magic happens when you order a Dealer’s Choice cocktail. You’ll pick a spirit (such as aquavit or mezcal), flavor profile (smoky, spicy, etc.), and glassware (a Collins glass or beer bong [kidding about beer bong]), and *poof* a unique cocktail made specifically for you appears. Abracadabra.




Simply put, Drumbar is stunning. This may lead some to believe that it’s the perfect spot for unfettered Snapchatting and throwing back rooftop mimosas like they’re vicious slam dunks. On the contrary, the real deal is that Drumbar makes some of the best cocktails in town, and any visit that includes Whitney Morrow’s seasonal cocktails and an epic lounge sesh in a tufted-leather sofa is really where the action is at.


The Whistler

Logan Square

Years before seemingly every neighborhood on the North Side had its own cocktail joint, the Whistler was drawing crowds to an unexciting stretch of Milwaukee Ave that mostly devoid of bars. Mixologist Paul McGee spent three-and-a-half years whipping up drinks here, but the bar is still going strong long after his departure. Patrons keep coming back for the live music and surprisingly affordable drinks, which range from $6 to $12, and seem like a downright steal when compared to some of the pricier options around town. The Whistler helped the craft-cocktail movement bloom in Chicago, but it hasn’t aged one bit.



Gold Coast

Sparrow is eye candy, which you wouldn’t expect to find this time portal of a lounge adjacent to some of the bro-iest bars in town, but there it is, sticking out like a sparkling needle in a stack of hay, waiting to whisk you away to 1940s Cuba. Inspired by a retro Havana hotel lounge, the bar’s art deco stylings can be soaked in for hours. And while Sparrow isn’t actually a hotel lounge, it does serve breezy rum cocktails such as the Hotel Nacional, made with pineapple rum, apricot liqueur, pineapple, and lime.

Courtesy of The Sixth

The Sixth

Lincoln Square

Kick back with a good drink at The Sixth, and you may start spacing out enough to think you’re currently in a Downtown lounge. Yet, the lack of pretension here will quickly snap you back to reality, because for all its spirits-mixing wizardry, The Sixth still has the soul of a buttoned-down neighborhood bar. Benjamin Schiller (Berkshire Room) is responsible for much of said wizardry, making drinks such as the Trix-inspired Silly Rabbit, and the Weston, which contains ingredients such as bourbon, Dark Matter coffee, and pipe tobacco. Both are mesmerizing.




Place your trust in Julia Momose's bar program, you'll be more enlightened for it. Even the less-favorite cocktails on the menu have the capacity to be bold, exciting, and make you understand what the bartender was going for. That’s the real draw of GreenRiver: it pulls no punches. It takes chances, and when it’s successful, the drinks nail the landing, gloriously. Add impressive food, head-turning views of Downtown, and the sexy Annex lounge, and you have one of the finest drinking environments in town.


Milk Room

The Loop

Upon first glance, Milk Room just seems like too much fuss, hidden away in a small section of the Chicago Athletic Association’s second floor, the bar has only eight seats. The drinks cost upwards of $50 each, and in order to visit, customers have to purchase a ticket in advance through Tock. For the masses, going through all this hassle is, as you can imagine, quite unimaginable. Yet, it’s worth it if you have a taste for the uncommon, because the bar stocks spirits that are, in some cases, not even replaceable. Drinks are made with decades-old bottles that have been acquired at estate sales and such, allowing cocktails to transport patrons back through time. For some, that’s priceless.


Lost Lake

Logan Square

For mixologist Paul McGee, the hits seem to keep on coming, aside from finding success at the Whistler, Three Dots and a Dash, and Milk Room, McGee has sprinkled some of his buzz-baiting pixie dust on Lost Lake. The charming tiki bar provides plenty of colorful drinks, rum bottles, and shareable bowls. But what really stands out, besides the quality of the drinks, is just how much fun everyone is having.

Freehand Chicago

Broken Shaker

River North

Surely two of the finest cocktail bars in Chicago cannot be located next door to each other? Alas, they are, and you should visit them en route to Truth, Meaning, and a great buzz. The Broken Shaker has some serious competition next door at the Berkshire Room. Yet, that has only elevated its game, as evidenced by wonderful cocktails such as the Trail Mix Old Fashioned, made with toasted whiskies, dried-fruit demerara, and chocolate-cherry bitters. Don’t sleep on the excellent bar-snacks either, or you’ll be waking up with backaches.  

The Aviary

The Aviary

West Loop

The Aviary is the kind of spot where you’ll always be worried whether you’re underdressed, and the drinks cost about $5 more than you’re used to. Regardless, the cocktails here verge on the fantastical, assaulting the senses with unfamiliar smells, shapes, flavors, and colors. Smoke, booze-filled ice spheres, ship bottles -- the Aviary serves them all with cocktails and does not give an eff. It’s the cocktail equivalent of seeing Avatar in 3D: not everyone’s cup of tea, but mind-blowing nonetheless.


The Violet Hour

Wicker Park

The Violet Hour is built on a foundation of confidence. It’s dark, hushed, and does not care for cell phones. Its façade is a mural-covered wall, and the draped interior shrouds the space to such an extent that it’s difficult to tell just how big the lounge is. Hell, the bar even made its own Malört. Yet, the seasonal cocktail menu is dependably impressive, and people still line up to grab a seat during peak times at this Chicago classic.



Logan Square

Scofflaw may be one of the best-loved bars in all of Chicago. It has plenty of critical accolades, and loyal patrons swear by this neighborhood spot and its excellent, reasonably priced cocktails. Sure, Scofflaw’s classification as a gin-centric bar is a bit overblown, but that’s because it carries tons of other spirits and prepares them equally as well. But, yes, you should order anything made with their handcrafted Old Tom gin, and stick around until midnight, when the kitchen hands out free fresh-baked cookies.

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1. The Berkshire Room 15 E Ohio St, Chicago, IL 60611

Inside the Acme Hotel in River North, The Berkshire Room is an old-time cocktail lounge that harks back to when the hotel was called The Berkshire Hotel from the 1920s to 1950s. The drink selection puts a heavy emphasis on barrel-aged cocktails, but the real stunner is the Dealer's Choice, essentially an off-menu cocktail based on your choice of spirit, flavor profile, and glassware. The space is dark and cozy with black-and-white tiled floors and a long, glossy bar.

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2. Drumbar 201 E Delaware Pl, Chicago, IL 60611

Not only is Drumbar one of the sexiest rooftop lounges in Chicago, the 18th-floor bar atop the Raffaello Hotel has a brag-worthy selection of whiskey, scotch, bourbon, and cognac. The sleek spot has a cozy den-meets-gentlemen's club decor with dark leather couches, wood-paneled walls, and a marble bar. During the summer, the seasonal outdoor patio makes it even more of an after-work drinking destination near the Magnificent Mile.

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3. The Whistler 2421 N Milwaukee Ave, Chicago, IL 60647

Started by two indie label owners/members of a punk acapella group (seriously), Whistler's a music venue so great, you'd happily hang out when no bands are playing: decked out w/ exposed brick, an L-shaped walnut bar top, reclaimed church pews and chairs with hymnal holders on back, and an intimate, nicotine-friendly back patio, where you can indulge in the habit that'll one day ensure daily prayer.

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4. Sparrow 12 W Elm St, Chicago, IL 60610

Inspired by 1940s Havana, this rum-centric cocktail bar is equal parts old-timey and cosmopolitan. The Sparrow was actually a lobby bar that first opened in the 1920s, and the restored space pays homage to the bar's Art Deco past with an old-school phone booth and a wall of room keys. Though you're definitely there to drink rum, there's also wide selection of other spirits and craft beer, both draft and bottled.

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5. The Sixth 2200 W Lawrence Ave, Chicago, IL 60625

The team behind Roots Handmade Pizza runs The Sixth, a whimsical cocktail bar with out-of-this-world concoctions that will forever change how you see handcrafted drinks. Take the Game of Thrones-inspired Bracer, a rye-based cocktail served in an ox horn mug or the Spaceman Spiff, a mezcal drink served with a saucer that releases citrus and cedar smoke once removed. We told you, out of this world.

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6. GreenRiver 259 E Erie St Fl 18, Chicago, IL 60611

Between its stunning views of the city skyline and Lake Michigan, an Irish American-informed cocktail menu, and inventive dishes like white fish tartine with egg, radish, and celery, and sturgeon with bean ragout, turnip, and kale, there’s much to love about this swanky Streeterville spot. The space is streamlined, airy, and modern, boasting an attached terrace complete with plush seating prime for lounging over whiskey-infused cocktails.

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7. Milk Room 12 S Michigan Ave, Chicago, IL 60603

On the second floor of the Chicago Athletic Association is Milk Room, a tiny bar that only seats eight people. Exclusivity is the name of the game here, as the literal hide-away requires you to purchase a ticket in advance. Drinks are pricey but since most of the spirits are rare and unusual finds, they're worth it.

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8. Lost Lake 3154 W Diversey Ave, Chicago, IL 60647

Chicago Tiki mogul Paul McGee (of Three Dots and a Dash) is behind Lost Lake, a temple to all things Polynesian in Logan Square. The cocktail bar serves rum-soaked classics and originals, including daily daiquiri specials and group punches, in tiki mugs and volcano bowls. Decorated like the original Don's Beachcomber Cafe, Lost Lake is decked out with banana leaf wallpaper and thatched bamboo but doesn't have the kitschy vibe of many tiki bars.

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9. Broken Shaker 19 E Ohio St, Chicago, IL 60611

An outpost of the fabled Miami hotspot, The Broken Shaker in Chicago is located at the upscale hostel (yes, hostel), The Freehand. The bar has a laid-back house party vibe with vinyl-spinning DJs, back-to-back rounds of Jenga, and cozy couches. Bottle service is traded for punch service and unique cocktails like the Trailer Park Smash (bourbon topped with Miller High Life) color the menu.

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10. The Aviary 955 W Fulton Market, Chicago, IL 60607

From James Beard Award-winning chef Grant Achatz (of Alinea fame), The Aviary is an ultra-posh cocktail bar that uses molecular gastronomy techniques to craft some of the prettiest cocktails you’ll ever have. To get a full taste of The Aviary, splurge on the multi-course cocktail tasting menu that pairs drinks with small bites. The speciality cocktails are pricey but the swanky experience is worth it.

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11. The Violet Hour 1520 N Damen Ave, Chicago, IL 60622

The first clue that this Wicker Park cocktail lounge is different from its neighboring bars is the house rules, the first of which forbids cellphones. The second is the James Beard Award-winning cocktail program. The drink menu is organized by alcohol type, and though you'll find vodka, brandy, tequila, gin, and rum cocktails, The Violet Hour's speciality seems to be whiskey, and a sip of the eponymous Old Fashioned confirms it. This is your Chicago destination for a night of refined, expensive drinking -- there is a dress code, and it's fancy.

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12. Scofflaw 3201 W Armitage Ave, Chicago, IL 60647

This classy bar in Logan Square will make a gin lover out of even the most gin-averse of clientele. It's one of Chicago's top cocktail bars because it proves that the versatility of gin extends far beyond the usual G&T and because it's outfitted with antique sofas that are palatial AND comfortable. Scofflaw also serves a menu of better-than-basic small bites, and the kitchen is open until 1am daily.