By Amy Tara Koch
August 12, 2014
Best Cocktails in Chicago
Credit: Courtesy of Scofflaw

While most of the nation dried up during Prohibition, Chicago came alive with notorious gangsters and their infamous speakeasies. Though many gritty gin joints disappeared at the end of the Golden Era, the stirring speakeasy aesthetic (and a certain bootleg-inspired irreverance) has been revived. This attitude—a combination of fearlessness and ingenuity—has evolved into today’s trailblazing cocktail culture. It appears in the charm of mismatched glassware at Scofflaw, and the boozy hideaways that admit entry only to in-the-know with the password. Here, you’ll find a painstaking appreciation for the liquor and the lifestyle that gave Chicago it’s rebellious reputation. Like chefs, bartenders are now bonafide craftsmen, turning out wildly creative concoctions that rely upon sophisticated flavor profiles and top-shelf liquor. Gone are the days of maraschino cherries and pre-mixed margaritas: the hallmark of a star mixologist may be their housemade bitters and syrups, or locally sourced garnishes. Hooch-making, it turns out, has served as the mother of cocktail invention.

Coq D’Or

Known as the second establishment in Chicago to score a post-Prohibition liquor license, this vintage boite is known for its generous martinis (four lush ounces, best enjoyed on the rocks). But it’s the ambiance—red leather booths, wood panelled walls, and an old time crooner belting out cabaret tunes on the piano—that truly pay homage to its bygone Prohibition days. Find Coq D’or behind the elevators at the upscale Drake Hotel.


Named for renegade boozers during Prohibition, this bar is a modern-day gin joint with a “spirit-forward” point of view and timeless décor. Cocktails are wildly inventive and wildly inexpensive, all $8. Sip your gin (frothy, citrusy, or straight) beneath the antiqued mirrors and white subway tile walls. For beer-meisters, there is a monthly “tap takeover” featuring a need-to-know-about brewery.

Billy Sunday

This high-concept Logan Square club pays close attention to each individual ingredient, from the exclusive bitters and colas to hand-hewn ice cubes. This turn-of-the century perch is even detail-oriented in its appearance, right up to the hammered-tin ceiling. Highbrow drinks include such highlights as the reimagined Harvey Wallbanger, served with a decorative (aromatic) side sachet.

Violet Hour

Pull back the plush cobalt-blue drapes and reveal parquet wood floors and whimsical leather chairs with exagerated high backs that, when grouped together, create near-private spaces for imbibers. The signless entrance does little to keep the extensive cocktail menu at this Wicker Park watering hole a secret. Try The Boss for scotch with lemon, Campari, carpano, and cold-brew coffee.

The Aviary

Just like his Michelin-starred restaurant, Alinea, Chef Grant Achatz ‘s upscale cocktail emporium is about combining flavor, presentation, and service into a collective high art. Here, bartenders are chefs and drinks are as complicated as a four star meal. Boozy bells and whistles (vapors, clove-infused ice, an interactive Bloody Mary) are an integral part of this high concept experience.