The Five Best Cocktail Bars in Chicago

In the Chicago of yore and lore, everyone drinks stirred martinis or bourbon with two ice cubes and wears a fedora hat that doesn’t make them look douchey. There’s a Tommy gun hiding in the folds of a trench coat, maybe, but it won’t do to touch the cool, grainy surface of an underground speakeasy bar. In the Chicago of present, these places are called "speakeasies" as an ironic statement meant to recover nostalgia of gangland movies and Prohibition and patrons wear plaid and thick-rimmed plastic glasses. There’s a Macbook tucked into a messenger bag, and nobody can afford to get even the slightest splash of herb-infused vodka on it. But the love is there, strong and discerning, for a hand-mixed and suitably stiff cocktail. So whether you’re looking for a return to the days of Prohibition blind pigs or a hipster venue to jam out to ABX while nursing a bespoke clove-infused rum cocktail, or a simple gin joint on a rainy night, follow the Chicago cocktail trail.

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The Violet Hour, for the discerning hipster

Violet Hour is the place to burn the midnight oil in vibrant Wicker Park. This cocktail bar is only in its seventh year, but it already has the reputation for being the Kingmaker of Chicago mixologists (its alumni include Brad Bolt of Bar DeVille, The barrelhouse Flat’s Stephen Cole and Mike Ryan from Sable). In a mega sports city like Chicago, the Violet Hour is a refreshing departure from the wings’n’beer sports bar, possibly the first of its kind – guests are treated by a sleek, airy bar with lush grey curtains, low light and hip but undistracting music, and professional and unpretentious bartenders who can really shake up a cocktail with flare. First-timers on a weekend evening shouldn’t be put off by the line – it looks busy from the outside, but the accommodating staff don’t ever let it get too crowded. House rules include: "No O-bombs. No Jager-Bombs. No Bombs of any kind. No Budweiser. No light beer. No Grey Goose. No Cosmopolitans." Say what you will about hipsters, but at least they have discerning tastes.

Jam out at The Whistler

Photo via their official FB page.

If The Violet Hour seems a bit stuffy for a cocktail bar (they may serve cocktails, but it’s still a bar), then The Whistler in Logan Square might just be the ticket. At less than $10 for a cocktail, their prices are certainly more relaxed, but that’s no indication of quality. Their constantly changing menu, which includes some of the most creative drinks in the city, has been consistently listed in "Best of Chicago" roundups and was one of GQ’s "25 Best Cocktail Bars in America." Cocktails aside, however, this place doesn’t try to be your grandad’s speakeasy – it’s a cool and casual bar, gallery, record label (whose roster includes The Hood Internet and Kid Static), venue that hosts live music and DJs seven nights a week, and a top jazz destination. Plus, the hipster force seems to be stronger than pretentious-cocktail-bar force in this one: broke hepcats can always order a PBR.

Scofflaw is a labor of love in the name of all that is gin

For a small and quiet, unpretentious gin joint that exists solely for the passion of this magical juniper-tinged and very British spirit, Scofflaw has become such a staple on the Chicago bar scene that people actually refer to the proprietors as "The Scofflaw guys" – see a neon sign advertising a new dive bar in Logan Square? Probably the Scofflaw guys. The Scofflaw Guys are alums of cocktail bars all over the city, united for the simple purpose of sharing their love of small, meticulously assembled small plates and gin-fused concoctions. What results is a die-hard fanbase, quick and delicious dinner tide-overs, midnight cookies for their midnight cowboys, and delectable and very reasonably priced cocktails (try the basil bramble with gin, lemon, briottet crème de mûre and basil). Of all the gin joints in all the towns in all the world, walk into Scofflaw.

The Drawing Room: go hungry

Fancy-pants in the Gold Coast historic district looking for a seasonal and scrumptious plate to tuck into accommodated by an expert cocktail should look no further than the Drawing Room, a 3-fork Michelin-awarded small, dark and unassuming lounge off Rush Street). It’s for an older crowd, a crowd that can afford expensive cocktails (which are, like, NBD in the Gold Coast anyhow) and a crowd that appreciates cocktail names such as The Old Man, the Monk and the Sea and the taste of complex flavors of coffee heering mixed with green chartreuse and xocolatl mole bitters, muddled with rosemary in an improved Irish coffee, or jasmine infused gin in the Ode to Aud.

The Barrelhouse Flat, the safest bet in town

For any occasion, the Barrelhouse Flat is an incredibly good bet. Headed up by a veteran of the Violet Hour, Stephen Cole, the menu offers every manner of cocktail, organized from stirred to shaken and spanning over four pages with a special focus on housemade bitters – plus, cocktail lovers who want a unique kick off the menu need only whisper a liqueur into their bartender’s ear and get exactly what they need. The food ranges from agreeable to knocked out of the ballpark with less than 10 seasonal options of small plates and a burger, ready sop up the booze – the pig face poutine, an occasionally present dish of fries, gravy and braised pork with a legendary reputation (like a fairy!) is an absolute must try. Made up of a crowd of (what else?) hipsters, preppy college students and cocktail nerds, Barrelhouse Flat is always a great decision.