When it comes to judging American cocktail metropolises, Chicago, one could argue, is a city second to none. With a lengthy list of longstanding speakeasy stalwarts like The Violet Hour, game-changing molecular-style ventures like The Aviary, and an ever-expanding selection of new places to try stretching from River North to Logan Square (and beyond), we’re inclined to agree. The city’s balance of creativity and accessibility have encouraged an atmosphere of risk-taking and experimentation that runs strong throughout its history—just look to its architecture, music, and recent culinary renaissance for proof—and its cadre of imaginative bartenders is in keeping with this rule. Here, we go inside eight of The Windy City’s best cocktail bars, including four of the greatest classics and a handful of the most promising newcomers.
Opened in the era of the cookie cutter speakeasy bar, The Violet Hour integrates a few of the trend’s most familiar elements—like a rules of behavior list and a somewhat hidden entry—while putting their own, more elevated spin on the aesthetics. Steering away from old timey Prohibition era trappings (tin ceilings, wood detailing, dark red accents) typical to other, kindred lounges, the bar takes on the appearance of a luxurious, modern private library instead. Heavy, blue-hued curtains divide the interior into three parlors with a fireplace at the farthest end. Dramatic, oversized blue leather chairs clustered throughout the rooms allow for small groups to gather without feeling squeezed. Even the barstools are thick and comfortable, making the white marble bar top feel welcoming rather than imposing. The James Beard Award-winning cocktail program offers a few classics (Old Fashioned, Brooklyn) alongside creative concoctions featuring culinary ingredients; think: the Little Death and a Long Sleep made with rum, lime, artichoke aperitif, and malted rye-walnut syrup. The only downside is that the bar doesn’t take reservations and the wait outside risks Chicago’s unruly weather. 1520 N. Damen Ave.; 773-252-1500; theviolethour.com.
Classic: The Aviary
Grant Achatz’s The Aviary takes some of the same core ideas behind his restaurants Alinea and Next—using scientific techniques and rethinking the restaurant experience on every level—and applies them to a cocktail bar with surprising success. Here, the bartenders are not the stars of the show (in keeping with the name, they are enclosed behind a large “cage”) leaving the drinks to steal the limelight. Most of the seating doesn’t face the bar at all, and high-backed benches hide it from view. The cocktails are mostly molecular drinks with showy elements like smoke, served in gourds and ship-in-a-bottle pouring vessels. But they’re also thoughtfully made, with touches like alcohol frozen into ice so that the drinks never over-dilute, and clever, with clear, bubble tea-like flavor-bursting spheres sitting invisibly inside a tall drink. Cocktail preparation is so intense that the bar employs a full-time “ice chef” to make over 30 styles of it in-house, and table service is as swift and impeccable as in a fine dining restaurant. 1520 N. Damen Ave.; 773-252-1500; theaviary.com.
Classic: Sable Kitchen & Bar
This all-day “New American gastro-lounge” (expect flatbread and sliders) on the ground floor of the Kimpton Hotel Palomar has been famous for its cocktail program for so long that they've dedicated a small chunk of their oft-changing drinks menu to highlighting their own house classics. The rest of the menu lists mostly seasonal (whole egg drinks and hot cocktails in winter) and/or culinary (Lapsang Oolong honey, Guinness-fig reduction) cocktails, with a great mix between beguiling refreshers and heavyweight bracers. Rounding out the menu is a section just for Spanish-style Gin & Tonics served in big goblets. It’s a hotel bar’s job to please all palates, and Sable does it better than most. 505 N. State St.; 312-755-9704; sablechicago.com.
Classic: The Berkshire Room
The Berkshire Room is a deceptively grand-looking modern classic bar in the Acme Hotel, replete with two-story ceilings, a classic black-and-white checkered floor, and dark-colored benches set into nooks for public socializing or private canoodling. The cocktail program is centered on barrel-finished cocktails (aged for a time in used whisky or wine barrels) and “dealer’s choice” (bartender-improvised) cocktails based on a drinker's descriptors or preferences. Though a very polished space, the bar's atmosphere is more lively than fancy, with complements like soft pretzel bites and “blue collar lagers” to keep the mood easy and unpretentious. 15 E. Ohio St.; 312-894-0945; theberkshireroom.com.
New: The Broken Shaker Chicago
Located inside the painfully twee hipster "hostel" The Freehand Hotel, The Broken Shaker is a bold concept in a small space. (It’s also the latest spin-off of the original Miami location.) The bar room off the lobby/lounge is over-decorated in bohemian chic, complete with macramé wall hangings, forest animal artwork, and a reggae soundtrack to complete the vibe. Whether that sounds irresistible or intolerable, you’ll find some of the most inventive cocktails in Chicago in this room—which is saying a lot for this mixology-forward city. Drinks have included a hot dog-inspired Margarita with spicy mustard pickle shrub, an Old Fashioned with cheese fat-washed bitters, and a Mai Tai with pistachio orgeat. The cool-kid atmosphere echoes the artsy-casual vibe, but the cocktails are serious business. 19 E. Ohio St.; 312-940-3699; thefreehand.com.
New: Green River
Green River is a no-expense-spared collaboration between New York restaurateur Danny Meyer and the team behind The Dead Rabbit, also in Manhattan—and rated the second best bar in the world. Though largely a restaurant space (the kitchen is run by local chef Aaron Lirette), the bar top impresses with a large array of bitters, syrups, and modifiers that probably outnumber the base spirits on the back bar. The drinks menu (like the Dead Rabbit’s) is quite long and can be intimidating even for connoisseurs; with so many seemingly incongruous ingredients (genever and tequila; rum and whiskey) listed for each drink, it’s difficult to guess how each will taste. It’s best to ask your bartender for advice: the entire staff is very well trained and will point you in the right direction. 259 E. Erie, 18th Fl.; 312-337-0101; greenriverchi.com.
New: Lost Lake
From one of Chicago’s most beloved bartenders, and the city’s top tropical cocktail expert, Paul McGee (formerly of Three Dots and a Dash), comes Lost Lake, a clean and unpretentious tiki bar festooned with banana leaf–print wallpaper and lobster trap lighting accents. The cocktails deviate from the expected all-rum format with gin-, scotch-, and tequila-based drinks filling out the list, though garnishes like dolphins carved from whole bananas and shareable flaming bowls ensure patrons remain on island time. 3154 W. Diversey Ave.; 773-293-6048; lostlaketiki.com.
New: Billy Sunday
Located not too far from Lost Lake in bustling Logan Square, Billy Sunday is the place to find Chicago’s best bartenders on their days off—a high compliment in any city. The rectangular room bears a slight resemblance to a posh British pub, but the food is mostly snacks in jars and on cheese boards rather than steak and potatoes. The venue is revered for its huge selection of bitter fernets and amari in bottles (no doubt a large part of its appeal to bartenders), as well as exciting “tonics” on tap made with exotic ingredients like flax seed, cedar berry, and dandelion. When in doubt, order the house Gibson: It’s been cited as one of the best in the nation. 3143 W. Logan Blvd.; 773-661-2485; billy-sunday.com.