Drinking in the Windy City

Charles K. Cowdery takes us to some of his favourite haunts in this North American city
By Charles K Cowdery
Chicago was established in the 1780s because its location, connecting the inland river system with the Great Lakes, was good for trade. One of its first buildings was a saloon. Since then, Chicago has never been without a formidable array of drinking establishments. Bars recovered quickly after the Great Fire of 1871, and even during the dark days of National Prohibition (1920-1933), thirsty citizens could usually find relief.

Chicago's illicit bars in those days weren't like the classic speakeasies for which New York is famous, with hidden entrances and whispered passwords. They operated more or less openly thanks to mutually beneficial co-operation between Al Capone's gangsters and Chicago's civic leadership, including its police.

Nelson Algren, the great literary chronicler of Chicago's seedier side, won his greatest acclaim for a novel about heroin addiction, but he was mostly a drinker. He drank whatever rot gut was cheap or, better yet, whatever somebody else was buying.

Chicago's drinking scene still has an 'anything goes' ethos, reflected mainly in its diversity. You can sip your whiskey in wood-paneled luxury or among inked-up punk rockers, the choice is yours.

Big Bar at the Hyatt Regency Downtown

151 East Wacker Service Dr, Chicago

The Big Bar is everything its name suggests. Intimate it’s not. But it is located right on the Chicago River, with clear views of some of Chicago’s most spectacular architecture, and it’s at the foot of the Magnificent Mile shopping district. Lake Michigan and the lakefront parks are nearby. It’s a convenient, come-as-you-are, train station sort of space that you don’t have to think about. The drinks selection is big too, of course, but this is not the place where you and a pal will explore whiskey and the meaning of life until the wee hours. It’s exuberant and superficial and that’s the pleasure of it. Big is a great place to meet for a drink or two, or to gather the crew for further nocturnal adventures. They have food, but that’s hardly the point.

Big Star

1531 North Damen Avenue, Chicago

A Texas roadhouse, serving stout, Bourbon and artisan tacos in the middle of the edgy Wicker Park neighbourhood? Why the hell not? Though less artsy than it used to be, Wicker Park still has a creative spirit and a re-purposed gas station on a large slab of asphalt just steps from the el (elevated train) station has been just what the neighbourhood needed. The asphalt expanse makes for great outdoor seating in warm weather, but the indoor space is relaxed and comfortable too. Indoors and out, spare décor pulls off the roadhouse theme. The food menu may be Tex-Mex but the bar is all Kentucky and Tennessee, with an exceptional Bourbon selection from people who know what they’re pouring.

Clark Street Ale House

742 North Clark Street, Chicago

For an atmosphere more like what you expect from a whiskey bar, head north on Clark Street into the River North neighborhood. As the name implies, you’ll find an awesome beer selection here but also more than enough Bourbon, rye, and single malt whisky to satisfy anyone’s passion. There’s comfortable seating indoors and out, and the vibe is warm and clubby without being stuffy. It’s in a low-rise stretch of 19th century storefronts surrounded by high rises. The neighbourhood, on the edge of downtown, is filled with bars and restaurants of every description, including a couple of blues clubs. The diner on the corner is a favourite with cabbies. The straightforward admonition of Clark Street’s ancient neon sign (“Stop & Drink”) is irresistible.


2771 North Lincoln Avenue, Chicago

Truly one-of-a-kind, Delilah’s is a whiskey bar where black clothing, piercings and body art aren’t required but certainly represent the norm. A love of loud rock-and-roll and tacky cinema also helps. A small space on two levels that occupies its own tiny building squeezed between two characterless monoliths, Delilah’s features esoteric art, Christmas tree lights, a crazy big Bourbon selection, plenty of Scotch, an unnatural amount of absinthe, and whatever else owner Mike Miller is obsessed with at the moment. Come early when seating and conversation are still possible, or come late for the spectacle.

Duke of Perth

2913 North Clark Street, Chicago

For Scotch lovers, the original is still champion. A small bar on an alley in Chicago’s Lakeview neighbourhood, little changed since it opened more than 20 years ago, the Duke bills itself as an authentic Scottish pub and features what is far and away Chicago’s best selection of single malts, including rarities. There are authentic ales and ciders on offer, unlimited fish & chips on Wednesday and Friday, no television sets, and that’s just what is touted on the window. The bar is nothing fancy, of course, but hospitable is a way that is more Midwestern American than Scottish, and that’s all to the good.


1970 West Montrose Avenue, Chicago

Chicago’s efficient and affordable public transportation system makes it easy to reach inviting neighbourhoods far from downtown without driving, and it allows an establishment such as Fountainhead to be both a neighbourhood joint and an eating and drinking destination. It’s a comfortable space with a knowledgeable staff, a great list of American whiskeys and Scotch, and a kitchen that emphasises local ingredients and original recipes. This is a good place to sample America’s new craft distillers, a quest upon which a knowledgeable guide is desirable. (And, just in case you’re wondering, the name has nothing to do with Ayn Rand, except they like the word for the same reasons she did.)

Longman & Eagle

2657 North Kedzie Avenue, Chicago

Chicago’s diverse neighbourhoods are where the fun is. Kedzie Avenue is the Main Street of Logan Square, site of a rare Chicago roundabout that circles a Doric column erected in 1918 to commemorate the 100th anniversary of Illinois’ statehood. Broad thoroughfares give the whole neighbourhood a park-like feel. Longman & Eagle is just a little north of the monument, on the east side of Kedzie at Schubert. You may need those directions because outdoor signage is minimal. Inside is a totally unique and original bar, restaurant, and inn that features local, seasonal foods, a constantly changing menu, and a thoughtfully assembled whiskey list from major and craft distillers on both continents. There are even six designer-created sleeping rooms, because you may never want to leave.


505 North State Street, Chicago

Although it is a temple to creative cocktails, Sable’s bartenders are among the best in town in their knowledge of straight spirits too. Combine the two by asking them to create an original cocktail featuring your favourite dram. Sable will orient you to the Chicago style of modern mixology. Or stick with whiskey neat. Sable’s digs in the heart of downtown are posh but comfortable and its ‘gastro-pub’ kitchen puts it in the top tier of local eateries. Although American whiskey is featured, imports don’t get short-changed. The bar has large windows for an intimate street view while the dining area is a little more private.