Eight of the best bars in Chicago

By: Ben Winstanley

November 12, 2015

Chicago is a city known for its electric bar scene, a place where the finest minds in mixology come to hone their skills. From innovative new creations to polished classics, the calibre of cocktails on offer could rival any city in the world. Whether you’re happiest in an old fashioned speakeasy or a contemporary cocktail laboratory, wet your whistle at some of these incredible bars in Chicago.


The Aviary

Eight of the best bars in Chicago | The Aviary
Experience boundary-pushing mixology at The Aviary © Edsel Little / Flickr

Cocktail bars don’t get much more exciting than this. Grant Achatz, the celebrated chef behind Alinea, has created an innovative cocktail concept at The Aviary that brings his trailblazing restaurant experience to world of drinks. Every scrupulous detail is taken care of by bartenders trained as chefs in a dedicated, high-tech drinks kitchen – there’s even an ice chef responsible for creating 30 different types of ice for the bar program.


The resulting cocktail menu delivers a wonderful array of innovative drinks. “The Junglebird” is a delicious science experiment on liquid densities: rum, Campari and pineapple-lime syrup sit as perfect individual layers, finished with rum “pearls” that pop in the mouth. Elsewhere, “Loaded to the Gunwalls” is served in a glass ship in a bottle and “In The Rocks” chills your drink inside an ice sphere to be cracked by a mini-slingshot device.



Eight of the best bars in Chicago | GreenRiver
GreenRiver is the brainchild of Danny Meyer, Jack McGarry and Sean Muldoon © Anthony Tahlier / GreenRiver

Without doubt the most anticipated Chicago opening of 2015, this elegant Irish concept was destined for greatness from the moment the collaboration was announced between renowned restaurateur Danny Meyer and Jack McGarry and Sean Muldoon of NYC’s beloved Dead Rabbit.


Choosing your order takes some time, as you sift through pages arranged by base ingredient rather than by spirit (rye, agave, juniper, etc.), but you’ll be rewarded for your perseverance. The drinks arrive with a host of potentially daunting components – a “Peace Frog” combines Clément Rhum Vieux Agricole, Cynar, Amaro, Amontillado sherry, Arrack, Black Trumpet mushrooms and Mirin. The bizarre location is just as unlikely as the flavours, 18 floors up a Streeterville hospital, but that hasn’t stopped GreenRiver establishing itself as one of the foremost cocktail bars in Chicago.


The Violet Hour

Eight of the best bars in Chicago | The Violet Hour
Step behind the velvet curtain at The Violet Hour © Michael Robinson

Credited as the forefather of the city’s burgeoning bar scene, this Wicker Park destination is widely regarded as one of the best bars in Chicago. The clue to the location, other than the snaking line on weekends, is the regularly changing graffiti mural that adorns the building’s frontage. The dimly lit lounge and bar wait behind an unmarked door, where seasonal cocktails revolve around various house-made concoctions and tinctures. The Violet Hour is by no means the new kid on the block, but it remains a local favourite.


The Drifter

Eight of the best bars in Chicago | The Drifter
The cocktail menu is printed on tarot crads at The Drifter © The Drifter, Chicago

Prohibition-style speakeasies are very a la mode in Chicago, but they can get a little tiresome. Punters clambering over one another to find the “secret” venues of retro-loving barkeeps, how nice it would be to find an authentic example of this amazing era. Enter: Liz Pearce, whose bar, The Drifter, is housed in a genuine former speakeasy. The cosy space beneath the Green Door Tavern retains much of its original décor, in what feels very much like a time warp.


A quirky drinks selection is printed on tarot cards, from which Pearce draws the daily menu at random. On rotation are the much-loved “Chocolate Negroni” and the “South American Mistress”, a smooth blend of pisco, vermouth and Fernet, balanced with chocolate liqueur and blackstrap bitters. The tiny stage, where occasional performances from burlesque dancers entertain the room, only goes to accentuate the vintage vibe.



Eight of the best bars in Chicago | Scofflaw
Try Scofflaw’s “Trust Fall” cocktail © You Me Us Now

One of the only gin-centric establishments in Chicago, Scofflaw takes its name from the prohibition term for a regular transgressor of the booze ban. Like its namesake, this is an idiosyncratic place with a hint of rebellion, individual for its mismatched glassware, baroque furniture and exposed brick interiors as well as for its imaginative use of gin.


Heading up the bar is co-owner Danny Shapiro with his own brand of retro style. Local favourite, “The Rocket Frost”, is just one example of what’s in store at this characterful establishment: Small’s gin, pear brandy, lime and grenadine, topped with an egg white “frost”.


Billy Sunday

Eight of the best bars in Chicago
Try classics with a twist at Billy Sunday © iStock / gregory_lee

Chef Matthias Merges shot to fame after his raved-about Yusho gave Chicagoans a taste for Asian street food. Now he has turned his talents towards a boozier establishment with this 50-seat cocktail spot in ever-popular Logan Square.


Billy Sunday begins in the “classic with a twist” spectrum of cocktail menus but soon gravitates to using familiar spirits as a point of departure for more interesting serves. Tonics and bitters, crafted by head barman Alex Bachman, offer a personal touch to most of the offerings.


Three Dots and a Dash

Eight of the best bars in Chicago | Three Dots and a Dash
Embrace the Tiki theme at Three Dots and a Dash © Anjali Pinto / Three Dots and a Dash

Tiki bars may conjure images of tacky decorations and sickly sweet cocktails, but this trend is taking the high road in Chicago. A blue light illuminating a tucked-away alley is the only sign of Three Dots and a Dash, but once inside, it’s a veritable Polynesian paradise.


The tropical island cocktails are the real draw to this venue, usually conjured from the 160-strong rum list. “Zombie Punch”, served in a glass skull, is the pick of the bunch: a heady mixture of Jamaican, Nicaraguan and overproof rum with lime, pomegranate, grapefruit and cinnamon.


Barrelhouse Flat

Eight of the best bars in Chicago
Try a Barrelhouse Flat “Whiskey Sour” © iStock / MauricioAvramow

A drinks menu of more than 70 serves awaits at this two-storey cocktail bar. Admittedly a little daunting at first, it won’t be long before you’re working your way though the list at Barrelhouse Flat (we’d recommend multiple trips).


Stephen Cole, a Violet Hour alum, brings his bag of tricks to a menu that picks from the pages of classic cocktail volumes. Some are more recognizable than others but, whether you plump for a “Whiskey Sour” or a “Swiss Ess”, you’re in for some of the finest classic cocktails around.


Virgin Atlantic makes it simple to book your flight to Chicago, bringing all these top bars within easy reach.


Have you visited any of these incredible cocktail bars in Chicago? Have we missed out any of your favourite haunts? Let us know in the comments section below.


Written by Ben Winstanley


Ben Winstanley

Ben Winstanley is a journalist with an unquenchable thirst for all things travel and gustatory. Invariably found at the table of London’s upcoming restaurants, his work has appeared in the likes of The Telegraph and Foodism. Beginning with long weekends travelling through Southern France and Spain, his curiosity to sample the world’s most vibrant cultures means it’s never too long before he’s ready for a new adventure. Though he’d never call it work, if there’s a better job out there, he doesn’t know about it. Follow him @ben_winstanley

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