The Barfly’s Guide to Chicago

By: Maxine Sheppard

April 19, 2011

Just in time for the start of our seasonal summer flights to Chicago (our direct, daily flights from London resume on May 9th) we bring you the latest guide to mixology heaven from our Flying Barman and Bacardi global ambassador Marc Plumridge…


The Violet Hour

Located in the thriving Wicker Park neighbourhood northwest of The Loop, this has to be my favourite bar in Chicago. If the Violet Hour is anything to go by, then the 1920s style ‘speakeasy’ is truly back with a vengeance, and this particular one is frequently featured in lists of the world’s top bars.


Taking selective stylistic inspirations from early 19th century French salons and English private members’ clubs, both of which played a huge role in developing the modern venue for drinking and socialising, the Violet Hour combines slick décor with a cocktail menu where you can still sense which base spirit is used, which is a joy to behold. Once you take a seat, try the Black River: a signature cocktail with Bombay Gin and macerated pineapple and other luscious ingredients including lemon and egg white.


The Violet Hour, Chicago © The Violet Hour

The Violet Hour, Chicago © The Violet Hour


1520, North Damen Avenue, Chicago

The Whistler

As you walk in you’ll be greeted by art installations and wonder if you’ve come to the wrong place. But once you find your way to the bar (via the discreet stencilled sign on the glass door or simply by the line of people paving the way) you’ll discover The Whistler most certainly is the right place, not just for every cocktail whim you can imagine, but for the curatorial skills of owners Robert Brenner and Billy Helmkamp.


As the founders of Chicago record label Whistler Records, Robert and Billy wanted to create a suitable venue for creative types to come and hang out that wasn’t just a bar, but a performance space for live music, poetry readings, film screenings and an art gallery.

The bar’s cocktail reputation was built on the back of head bartender Paul McGee, previously of Wolfgang Puck, who put together an inspired list of classic serves as well as selections where the boat has been well and truly pushed out. I suggest starting off the night with a Penicillin, made up of blended whisky, ginger, lemon and honey and finished with a flourish of Islay whisky for the discerning aficionado. If something lighter is more your thing, try a gin-based Torrino Fizz.


2421, N Milwaukee Ave between Fullerton Ave and Richmond St, Chicago

The Drawing Room

Since opening in 2007 the Drawing Room has gone from strength to strength, continually creating all manner of innovative liquid libations for its guests, be it punch bowls, handmade sodas, hand crafted cocktails or simply a twist on something taken from the array of well chosen spirits adorning the back bar.


What I like about this place is the natural interaction between staff and guests. Order a cocktail “˜tableside’ and the bartender will explain how and why certain flavours are paired together, which makes the whole experience more personal as your drink is made right in front of your eyes. Try a signature serve from the menu like The Old Man, the Monk & The Sea or simply ask the bartender for an interesting blend of ½ an ounce of Benedictine served up in a flute, spritzed with chilled prosecco.


The Dining Room © The Drawing Room Chicago

The Dining Room © The Drawing Room Chicago


937 N. Rush St. Chicago

Le Bar at the Sofitel Chicago Water Tower

Rethinking the notion of a “˜hotel lobby bar’, the super-sleek Sofitel Chicago Water Tower’s Le Bar is open and inviting, with a cosy library area, floor to ceiling glass walls and great views of the street, making it perfect for everyone’s favourite pastime whilst sipping cocktails – people watching.


Located downtown in Chicago’s North Side, you’re only moments from the Magnificent Mile, Navy Pier, Museum of Contemporary Art and Chicago’s upscale boutiques, so after a day of hardcore sightseeing come back and relax with a house Corpse Reviver, or make your choice from the menu’s serious selection of absinthe based cocktails, speciality martinis and more classics alongside.


Le Bar @ Sofitel Chicago Water Tower

Le Bar @ Sofitel Chicago Water Tower ©


20 E. Chestnut Street, Chicago 

The Aviary

The soon-to-open Aviary, billed as an ‘experimental drinking den’ by the New York Times, has been causing no end of anxiety amongst the cocktail elite, as its opening date continues to shift into the future. It’s most recent deadline of April 13th has been and gone, and now we’re told “this week” – but keep an eye on their Facebook page for updates. Regardless, this nearly-ready haven for cocktail enthusiasts is expected to substantially raise the bar for other establishments to follow – think the drinks equivalent to Heston Blumental’s Fat Duck restaurant in Bray, England and you’ll be halfway there…


Designed by renowned chef Grant Achatz, (from the restaurant Alinea where he made his name) Aviary sits alongside his new ticket-only restaurant Next in Chicago’s Fulton Market District (also soon to open), and is sure to wow every guest that takes a seat at the bar.

In addition to Aviary and Next, rumours are that there is a third space within the premises called the ‘Office’; an uber exclusive basement den which is by invitation only. How do you get in? Well, the guys say if they sense a true cocktail enthusiast sitting at the bar you’re in with a chance!


955 W. Fulton Market, Chicago

Virgin Atlantic’s summer season of flights to Chicago resumes on May 9th. Log on to for the very best fares.


Maxine Sheppard

Maxine is the co-editor of the Virgin Atlantic blog. Travel and music are her joint first loves, and despite having written for Virgin for more years than she cares to remember she still loves nothing more than jumping on a plane in search of new sights and new sounds.

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