Explore 30 of Chicago's whiskey secrets

From hidden speakeasies to confidential cocktails, we teamed up with Bulleit Bourbon to uncover Chicago's whiskey secrets
Photograph: Jaclyn Rivas
By Time Out Chicago in association with Bulleit |
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Chicago is a whiskey town. We like it neat, on the rocks or mixed into an expertly crafted cocktail. Most of all, we like finding places around the city with deep whiskey lists and bartenders who know how to put them to use. We’ve teamed up with Bulleit Bourbon to explore Chicago’s whiskey secrets, so you can enjoy a drink with similarly in-the-know individuals. Don’t worry about keeping this information confidential—like a great bottle of whiskey, it deserves to be shared.

Please Enjoy Bulleit Frontier Whiskey Responsibly

Chicago's best whiskey secrets

1
The Drifter
Photograph: Martha Williams

The Drifter

Those looking for a Prohibition-era haunt will find few more authentic than the Drifter. Located beneath the Green Door Tavern—itself a former speakeasy—this 45-seat cocktail bar is only accessible via a “secret” basement door. Once admitted, patrons can order drinks printed on custom tarot cards while taking in the period-appropriate antique decor and an array of unpredictable performers, from burlesque dancers to magicians.

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Photograph: Jaclyn Rivas

Binny’s Beverage Depot Whiskey Hotline

Boasting aisle after aisle of spirits, beer and wine, Binny’s Beverage Depot has long been one of the city’s premier liquor purveyors. The company also offers an important public service: a Whiskey Hotline (888-817-5898), staffed by a crack team of whiskey experts. They’re available to answer your most pressing whiskey-related questions or help you track down that rare bottle you’ve been chasing. Every city should have a hotline this useful.

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The Office at the Aviary

The Office at the Aviary

Everyone knows the Aviary produces some of the most forward-thinking cocktails in town, from its signature Porthole-infused drinks to a deconstructed Moscow Mule. But not everyone knows about the hidden speakeasy in the bar’s basement. Once an invite-only hangout, the Office is a little easier to get into these days—you can actually make a reservation—and its whiskey library is as intriguing as the mixed drinks.
Recommended by mixologist Charles Joly

4
The Crown at Howells & Hood
Photograph: Jaclyn Rivas

The Crown at Howells & Hood

If you’re going to throw a party in Chicago, you might as well do it in a venue with a view. On the 25th floor of the Tribune Tower, The Crown event space offers a unique 360-degree perspective of the city and the river. Because it’s operated by Howells & Hood, you can also look forward to a selection of Scotch, bourbon and local whiskeys. Admit it: If your office threw a party here, you’d actually want to go.

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5
Fountainhead Barrel Room
Photograph: Andrew Nawrocki

Fountainhead

This Lincoln Square bar is known for its extensive beer selection, but the whiskey lists at Fountainhead are equally impressive. Take a seat in the Barrel Room—a small room tucked behind the main bar—and peruse the meticulously arranged menu, which includes single cask selections. Want to take some whiskey home with you? Grab a bottle from the adjacent Fountainhead Market and conduct a tasting from the comfort of your own couch.

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Photograph: Jason Little

Heavy Feather

The nightlife in Logan Square seems to revolve around Slippery Slope, a bar that features cheap beer, bottled cocktails, loud music and (usually) a line out the door. However, not everyone is queued up to hit the dance floor—a set of stairs inside leads to the Heavy Feather, where classic cocktails are served in a wood-paneled space styled after a ’70s-era fern bar. Taking a trip back in time is as easy as sinking into one of the leather chairs and ordering an old-fashioned.

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Photograph: Courtesy Chop Shop

Chop Shop

Located in a Wicker Park warehouse that used to house an auto body garage, Chop Shop is an eating and drinking paradise. The first floor of the venue is a truly multipurpose space, with a deli, a butcher shop, a full-service bar, a restaurant and an expansive event venue that sometimes hosts concerts. Escape the crowds by going upstairs, where you can drink at Chop Shop’s second bar and order that house-made sausage you had your eye on.

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View from the Signature Lounge

Signature Lounge ladies' room

Situated on the 95th floor of the John Hancock Center, the Signature Lounge is known for its breathtaking sights and excellent drinks. With a seasoned bar staff that averages 20 years of experience, you’ll have no trouble ordering the perfect Bulleit cocktail. Female whiskey-lovers take note: The ladies’ room boasts some exclusive views that you can Instagram to your heart’s content.

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9
Maria’s Packaged Goods & Community Bar
Photograph: Jaclyn Rivas

Maria’s Packaged Goods and Community Bar

Bottles of all shapes and sizes line the walls (and windows) of Maria’s Packaged Goods and Community Bar, a family-owned slashie and favored neighborhood gathering place in Bridgeport. Pass through a gap in the store’s shelves and you’ll enter the tavern, where patrons can partake in cocktails as well as meat pies from the adjacent Pleasant House Bakery. Don’t worry if it’s your first time—everyone who steps into Maria’s is treated like a regular.

10
Untitled Supper Club
Photograph: Jaclyn Rivas

Untitled Supper Club

Discreetness is the rule rather than the exception at Untitled Supper Club in River North. Visitors enter through a pair of unmarked doors that lead into the underground complex, while VIPs come in through a separate entrance across the street and connected by an underground passage. Upon arrival, you’ll find a dining area, five bars, a stage for live music and a dance floor. Make sure to visit the Whiskey Library, an entire room dedicated to housing more than 500 kinds of whiskey that are available for sampling.

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11
Delilah's
Photograph: Max Herman

Delilah’s

This unassuming Lincoln Park bar may look like another dingy dive, but Delilah’s hosts one of the country’s most extensive whiskey selections—more than 750 varieties, to be exact. While you’re perusing the list, you’ll be treated to loud music, vintage films on the TVs and the chatter of a diverse crowd that ranges from young college students to old regulars. Head upstairs and you’ll find a lone pinball machine tucked away in a corner, just waiting for you to set a new high score.

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Lady Gregory's
Photograph: Andrew Nawrocki

Lady Gregory’s

Named for an Irish author, Lady Gregory’s is an Andersonville pub lined with bookshelves instead of the usual collection of stereotypical Emerald Isle tchotchkes. Behind the bar, you’ll find a refined selection of 300 whiskeys, available separately or as part of a sampling flight. Want to throw your own tasting party? The gorgeous Cellar Room in the back of the bar can be rented for private events. 

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13
The Monkey's Paw
Photograph: Max Herman

The Monkey’s Paw

What’s the best way to wash down a plate of poutine prepared with farm-to-table ingredients? Whiskey, of course. Luckily, there’s plenty to choose from at the Monkey’s Paw, a neighborhood gastropub on the west side of Lincoln Park. You can solicit a suggestion from one of the knowledgeable bartenders, try a bourbon flight or pick one of the rotating whiskey cocktails on the menu—rest assured, you’ll relish your decision.

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Sable Kitchen & Bar
Photograph: Colin Beckett

Sable Kitchen & Bar

As far as hotel bars go, few in Chicago are as outstanding as the Sable Kitchen & Bar. On the ground floor of Hotel Palomar, it’s the kind of place that serves oysters and fried chicken alongside delightful cocktails. With a menu that includes spirit-forward concoctions as well as solid reinterpretations of classic drinks, you may have to think about getting a room at the hotel after spending a few hours at the bar.
Recommended by The Drifter co-owner Liz Pearce

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15
Photograph: Jaclyn Rivas

Twisted Spoke

The skeleton atop a motorcycle hanging outside may make you think Twisted Spoke is a biker hangout, but the decor isn’t exactly indicative of the West Town bar’s clientele. This a place for whiskey lovers of all stripes, with more than 300 different bottles to pair with menu items like fried egg sandwiches, burgers and pulled pork. Come by on a Wednesday and you can drink any whiskey in the house for half-price. 

16
Iwan Ries & Co
Photograph: Brendon Brown

Iwan Ries & Co Tobacco Lounge

Cigars and whiskey are said to be a perfect pairing, but there are very few public places where you can smoke while sipping a drink. Iwan Ries & Co is one of those places—a family-owned tobacconist that has been headquartered in Chicago since 1857 and houses a luxurious smoking lounge. Located in the back of the store, the lounge features Wi-Fi, TVs, plush chairs and—best of all—it’s BYOB. Bring along a bottle of Bulleit and pour yourself a glass to go with your stogie.

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17
Clark Street Ale House
Photograph: Jaclyn Rivas

Clark Street Ale House

The warm glow of a neon sign that reads “Stop & Drink” beckons you into this casual River North bar. Clark Street Ale House boasts a diverse crowd of 20-somethings, white collar workers and tourists, attracted by the bar’s deep beer list and its extensive whiskey menu, which includes more than 85 single malt Scotches. It’s open until 4am each night, there’s a patio out back and you can bring your own food—what’s not to like?

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Billy Goat Tavern
Photograph: Grace Allen

Billy Goat Tavern

Though it’s best known for its signature “cheezborger,” the original Billy Goat Tavern is also a great place to go for a stiff drink. To get to the subterranean pub, you’ll need to venture below Michigan Avenue—just look for the glowing neon signs. Once inside, you’ll find walls covered with old photos and newspaper clippings, plus a clientele consisting of regulars, tourists and (inevitably) people quoting the old Saturday Night Live sketch that made the tavern famous. 

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19
Duke of Perth
Photograph: Max Herman

Duke of Perth

Best known for its all-you-can-eat fish and chips specials (available on Wednesdays and Fridays), the Duke of Perth is a classic Scottish pub, complete with an expansive whiskey selection. You’ll find Scotch from all over Scotland, from single malts to blends, available separately or as part of a flight. Order something straight up or on the rocks and enjoy it in the tchotchke-strewn interior or sip it outside on the beautiful garden patio. 

20
Bar on Buena
Photograph: Max Herman

The Bar on Buena

With its great selection of beer and whiskey, it’s no surprise that this neighborhood bar in Uptown is owned by the same team behind Lincoln Square’s beloved Fountainhead. Owner Aaron Zacharias keeps a deep list of Scotch and bourbon on hand, offering cleverly named flights (“3 Island Tour”, “For Peat’s Sake”) for whiskey-lovers afraid of commitment. Start drinking your way through the menu on Thursdays, when all flights are 25% off.
Recommended by beverage director Peter Vestinos

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Photograph: Martha Williams

Sportsman’s Club

At the Sportsman’s Club, Low Life isn’t a derogatory term, it’s just the name of a $5 beer and whiskey shot combo. Located in a former Polish dive bar, you’ll find a rotating cocktail menu, tables that double as checker boards and whiskey-to-go at this Ukrainian Village spot. Ask for a look at the reel-to-reel tape machine hidden behind the bar, which provides a pleasant mix of contemporary and Polish rock tunes.

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0613.chi.rb.jo.BerkshireRoom02.jpg
Photograph: Martha Williams

Berkshire Room

The bartenders at the Berkshire Room don’t just make great cocktails, they make cocktails that are aged in whiskey barrels. Housed in the Acme Hotel, this is the kind of bar that likes putting its wide array of whiskey and Scotch to use. The Dealer’s Choice cocktails allow you to choose a spirit (Bulleit, perhaps?), flavor profile and preferred glassware, before allowing the staff to construct a drink tailored to your specific tastes. Recommended by Sportsman's Club bartender Jacyara de Oliveira

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23
M Bar
Photograph: Jaclyn Rivas

M Bar

When the weather outside is frightful or you’re just in a rush, there’s no better way to navigate downtown Chicago than the Pedway, a series of underground tunnels that snake through the Loop. It’s also not a bad place to go for an after-work drink, if you know where to go. Your best bet is M Bar, a sizable sports bar located underground in Millennium Station. Go ahead and have some whiskey before you board your train—it makes the ride go by faster.

24
Ceres Cafe
Photograph: Grace Allen

Ceres Café

Named for Ceres, the Greek god of agriculture that graces the top of the Chicago Board of Trade, this café is a downtown institution. Some visitors come to eat the Greek diner fare, but most arrive to partake in the location’s hidden specialty: some of the strongest whiskey cocktails in the Loop (and perhaps the city). During the summer, you’ll find the outdoor patio packed with people who have slipped away from work for an early happy hour—feel free to join them.

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25
Weegee's Lounge
Photograph: Grace Allen

Weegee’s Lounge

If you’re looking a place to drink whiskey cocktails like the ones your grandfather used to, this retro-styled bar on the western edge of Logan Square should do the trick. Settle into a seat at Weegee’s Lounge and order a Rusty Nail or an Old Fashioned before you show off your skills on the shuffleboard table or sit for a portrait in the photo booth. The fun doesn’t end indoors—a sizable patio is one of the best in the neighborhood.

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Schwa
Photograph: Zach Long

Schwa

With only 26 seats and a notoriously difficult reservation system, Schwa is one of the hottest dining experiences in Chicago. If you manage to get in, you’ll be served by chef Michael Carlson, who indulges in adventurous dishes like his signature quail egg ravioli. The restaurant is BYOB, and guests are encouraged to bring drinks for the hard-working kitchen staff, so take an extra bottle of Bulleit if you want to make some new friends.

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The United Center’s Bulleit cocktail

Want to enjoy a whiskey while cheering on the Bulls and Blackhawks at the United Center? Take a time out and visit Lillie’s Q (on the 200 level) to indulge in some barbecue and ask for the exclusive Bulleit Bourbon Lemonade. The classic southern cocktail blends freshly squeezed lemons and pure cane sugar with the spicy character and smoky backbone of Bulleit—the perfect complement to an exciting game.

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The Sky-Line Club opened its doors to visitors during Open House Chicago on October 19, 2014.​
Photograph: Max Herman

The Sky-Line Club

It’s not exactly a secret, but you will have to pony up a monthly membership fee if you want to drink at the Sky-Line Club, a private social club on the 24th floor of a Michigan Avenue high-rise. Members gain access to a reconstructed 1920s English pub, where quality food and drinks are accompanied by exquisite views. Your best bet for admittance without a membership? Show up to an event hosted at the club (and wear something nice). 

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29
Izakaya at Momotaro
Photograph: Huge Galdones

Momotaro’s Izakaya bar

The modern Japanese cuisine takes the spotlight at Momotaro, but the Izakaya bar in the restaurant’s basement is a secret worth sharing. Boasting one of the city’s largest arrays of Japanese whiskeys, the subterranean watering hole also offers its own menu of food to sample while you drink. Head down for a pre-dinner snack, or skip the wait for a table and spend your evening at the bar.

30
The Franklin Room
Photograph: Martha Williams

Franklin Room’s Whiskey Keep program

Situated below street level in River North, the Franklin Room describes itself as a modern-day speakeasy, equipped with a wide selection of whiskey (all available with quarter-bottle service) and an extremely knowledgeable bar staff. The bar’s unique Whiskey Keep program allows visitors to buy bottles of rare off-list whiskeys, which are stored up in a cabinet so they can be shared with friends (or not) on future visits. It’s like your own downtown whiskey clubhouse.

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