Drumbar Chicago

Find your way to some of Chicago's swankiest speakeasies with ambience and offerings straight from the Roaring ’20s (©Anthony Tahlier)

Chicago’s New Speakeasies

By Valerie Moloney on 11/08/13, updated 01/31/14
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While Al Capone and John Dillinger no longer roam its streets, Chicago will always have a fascination with its seedy history. In particular: Prohibition-esque bars that throw back to an underbelly of free-flowing booze and live music. Today, the taste for stiff drinks lives on in these modern Chicago speakeasies:

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No password required to enter this River North den sandwiched between a parking garage entrance and a CVS. Follow the heavy wood doors down to a massive, liquor-filled chamber sporting masculine flair in the way of tufted leather couches and personal whiskey lockers. (Off-the-clock locals choose from more than 300 kinds of whiskey, in fact.) The showpiece: a stage that hosts big bands, burlesque dancers and soul brunches. 111 W. Kinzie St., 312.880.1511
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The Violet Hour

Another speakeasy, another discreet entrance—this one just south of Wicker Park’s pedestrian-heavy Six Corners—sometimes distinguishable by a mural. Called “ground zero for cocktail culture” by Details magazine, The Violet Hour woos a certain kind of drinker, the one who doesn’t mind waiting a little if it means the bartender will use housemade bitters and fresh-squeezed juices to craft taste profiles that stand to be a lot more memorable than a vodka cranberry. Tall-backed, solo leather chairs and sweeping curtains lend drama, which seems apropos if you’re about to taste the bitter, in-house Malört for the first time. 1520 N. Damen Ave., 773.252.1500
The Violet Hour

 

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Hidden in the Raffaelo Chicago, this Gold Coast lounge with its tufted leather couches and private outdoor patio is both the place to enjoy a hand-crafted cocktail and to hear Michael Jackson on a Saturday night, or so say the barmen. Read: great drinks, lack of pretension. Beverage director Alex Renshaw and his team do wonders with scotch, whiskey, bourbon, rum and gin, balancing the bitter with the sweet, the sour with the spice. Oh, and there’s that other accolade, too: Being named one of the best new bars in America in 2013, also by Details Magazine. 201 E. Delaware Pl., 312.924.2531
Drumbar

 

Sable

A night may start at a restaurant and end at a corner tap for drinks—unless, of course, you’re staying at Hotel Palomar, which is lucky enough to have two solid options on site. Rooted in mixology as alchemy, the beverage program relies on juices, juice purees and other ingredients sourced from local producers. Sip on cheekily named drinks including “Overworked and Underpaid” and “Rehab Doll,” which boast style and substance—just like the industrial chic dining room. 505 N. State St., 312.755.9704
Sable

 

The Barrelhouse Flat

Let bygones be Barrelhouse, the Lincoln Park speakeasy that eschews the neighborhood’s typical sports-bar vibe for vintage cocktails and punches in a circa-1892 building. Bypass the first floor for a seat in the upstairs lounge, whose red velvet, high-backed chairs, fireplace, old-timey jukebox, piano and billiards table evoke a time gone by. 2624 N. Lincoln Ave., 773.857.0421
Barrelhouse Flat