Chicago’s ‘Mad’ About Mixology

The Very Best Cocktail Lounges in the Windy City

Long before “Mad Men” hit the airwaves, the Windy City was known as a hardcore drinking town. Beer, shots and the occasional three-martini lunch were most people’s poisons of choice until the 1960s-based AMC series helped usher in a cocktail revolution.

So now imbibers--from locals to visitors--seek out expertly made elixirs. Who gets it done right for those looking for classic and contemporary tipples? New and old, we’ve gathered a great list of places to go for the best in Chicago mixology.

  • 01 of 09

    Aviary/The Office

    ••• Photo courtesy of The Aviary

    When it comes to cocktail lounges, Aviary’s in a class by itself. The award-winning watering hole is the brainchild of molecular gastronomy master Grant Achatz, and the drinks follow a similar culinary philosophy. Bartenders, in fact, are dubbed “sous chefs” and arrive several hours before opening to prep ingredients. The results are magical, with fresh perspectives and seasonal renditions of classic cocktails such as the Manhattan, Champagne cocktail and Old Fashioned. Directly underneath Aviary is The Office, a tiny, invite-only space that seats about 18 guests for drinks and small plates. Both bars boast a massive whiskey list with rare scotches and bourbons as well as progressive whiskey flights. 955 W. Fulton Market, 312-226-0868

  • 02 of 09
    ••• Photo courtesy of Barrelhouse Flat

    Lincoln Park is home to more bars than we can count, but when it comes to contemporary cocktail culture, Barrelhouse Flat obsesses over every detail. From the décor of old-timey, reclaimed fixtures to give it an authentic atmosphere to the comprehensive list of classic drinks, you’d think you stepped back in time. They get extra bees in their bonnets for perfectly matching the mixology program with the food, which changes seasonally. 2624 N. Lincoln Ave., 773-857-0421

  • 03 of 09
    ••• Photo courtesy of Drake Hotel

    Bar trends come and go, but one thing has always been consistent: Coq D’Or has outlived them all. The Drake Hotel’s dimly lit lounge has been around since the repeal of Prohibition and it maintains an authentic, sophisticated setting. Bartenders are well-seasoned and no-nonsense, with great storytelling skills. Their domain is a great place for settling into mid-week for something strong and stiff (Think Old Fashioned, whiskey neat). 140 E. Walton St., 312-932-4623

  • 04 of 09
    ••• Photo courtesy of Drumbar

    Another hotel bar, Drumbar looks and feels like the type of place that would have gotten plenty of Don Draper action back in the 1960s. It’s located on the 18th floor of the Raffaello Hotel and features a bustling outdoor rooftop patio during warm months. While the classic cocktail list is the obvious choice for drinking around these parts, the progressive menu should pique the interest of those more adventurous. That list is seasonal and experimental with rare ingredients and hard-to-find spirits. Drumbar also boasts an extensive collection of rare finds when it comes to scotch. 201 E. Delaware St., 312-943-5000

    Continue to 5 of 9 below.
  • 05 of 09
    ••• Photo courtesy of Gilt Bar

    Serving as a great after-work watering hole, Gilt Bar is located directly across the street from Merchandise Mart. A highly sought after bar is carved out of the spacious dining room, and that’s where the bartenders work their magic with renditions on the Champagne cocktail, whiskey smashes and more. The lower level is home to The Library, an intimate drinking room with leather-bound classic novels that you can read while sipping one of the many options. 230 W. Kinzie St., 312-464-9544

  • 06 of 09


    ••• Photo courtesy of Matchbox

    You don’t have to be a social butterfly, but you’ll need to be comfortable bumping into your neighbor on a regular basis if you go drinking at this tiny corner bar that’s been measured at 400 square feet. At least there’s an incentive: Order a cocktail and you’ll get a sidecar that’s enough for a full second drink. Signature cocktails are Gimlets and Manhattans. 770 N. Milwaukee Ave., 312-666-9292

  • 07 of 09
    ••• Photo courtesy of Sable Kitchen & Bar

    The swanky Palomar hotel’s lobby bar attracts more locals than visitors. And while the bartenders have all the tricks of the trade to make exotic elixirs and such, they’re swift. You’ll have that cocktail in front of you in the same time it takes for them to crack open a beer. They’re also big whiskey aficionados, so the selection is vast. The “liquid library” is comprised of cocktails made with local and house-made ingredients. 505 N. State St., 312-755-9704

  • 08 of 09
    ••• Photo courtesy of Three Dots and a Dash
    Forget everything you’ve ever known about tiki-inspired cocktails. Lettuce Entertain You Enterprises’ upscale Polynesian pub re-invents everything from the Beachcomber to the Zombie. Guests walk through a lit-up alley on Hubbard Street and head downstairs for the action, which includes female servers in hula skirts, a lively crowd and music ranging from 1960s surfer tunes to old-school hip-hop. 435 N. Clark St., 312-610-4200


    Continue to 9 of 9 below.
  • 09 of 09
    ••• Photo courtesy of Violet Hour

    It’s been credited with pioneering Chicago’s current mixology scene, and Violet Hour continues to thrive--even on what’s considering “off nights” for most bars. Some of VH’s policies have been widely criticized (no cell phones, 15-minute waits for cocktails, every customer must have a seat), yet there’s a line around the corner to get in almost every night of the week. The staff dresses immaculately, perfects every cocktail and maintains a calm demeanor in the face of even the most agitated customer. 1520 N. Damen Ave., 773-252-1500