Chicago's 10 Best Whiskey Bars
Lady Gregory's

Fact: the Latin translation for the word "whiskey" is "water of life." Another fact: our bodies are 2/3 water. Obvious conclusion: our bodies need whiskey to survive. Assuming you don't want to die, here're Chicago's 10 best whiskey bars.

Delilah's (click here for address and deets)
Lincoln Park
If the blaring punk and metal doesn't melt your face, drinking from the wrong cup in the third Indiana Jones movie totally will. That, and Delilah's unfathomable whiskey selection -- she boasts more than 600 brown booze varietals (including offerings from every region in Scotland), her own limited edition 20th anniversary blended whiskey with the UK's Compass Box, and daily bourbon deals for $3 or less.

Berkshire Room (click here for address and deets)
River North
Not only are the walls made from a salvaged Kentucky distillery, and its cocktails finished in Pappy Van Winkle barrels, but Berkshire’s 200+ whiskeys are boosted by a secret off-menu reserve that reads like a bootlegger's to-do list.

Longman & Eagle

Longman & Eagle (click here for address and deets)
Logan Square
Longman’s credo? “Eat, Sleep, Whiskey” – all three of which you can do at the gastropub and inn. Start with a wild boar sloppy joe topped with pickled jalapeno, and wash it down with flights of Bernheim Wheat Whiskey/Knob Creek Single Barrel Reserve 9 yr/Willett 21 yr. Then, if you don’t feel like walking home, stay at the bar’s boutique, six-room hotel upstairs to finish off the full-service whiskey experience.


Drumbar (click here for address and deets)
Gold Coast
The Raffaello Hotel's 18th-floor-oasis offers lake views, fire pit-equipped tables, and whiskey cocktails aplenty, including a classic Blood and Sand they do with Famous Grouse blended Scotch.

Duke of Perth (click here for address and deets)
This Scottish bar boasts Chicago's largest collection of single malt whiskeys, punctuated by a cask-proof 30-year-old Glen Ord that'll blow your kilt away (we mean figuratively... hopefully).

Monkey’s Paw (click here for address and deets)
Lincoln Park
This Monkey’s Paw will grant you three wishes, just as long as those three wishes are poutine, craft beer, and a whiskey wall stocked with 50 single malts.

Twisted Spoke (click here for address and deets)
West Town
Half-price whiskey Wednesday has a beautiful ring to it. And so does 300 whiskeys, 200 beers, burgers, and a rooftop patio.

Untitled (click here for address and deets)
River North
Because hard liquor and nudity go together like Donatello and purple outfits, take in both at this spacious Prohibition-era supper club, which features a complementary burlesque show and a 400-deep whiskey menu.

Old Fifth (click here for address and deets)
West Loop
It has to be kismet when, while excavating their West Loop industrial space, Old Fifth’s owners turned up a ceramic liquor bottle from the Prohibition era. Now it sits on a shelf along with 140 other whiskeys, including distilled offerings from local favorites Koval and Few. And for things that are not whiskey but are still great? Double-decker pizzas.

Lady Gregory's

Lady Gregory's (click here for address and deets)
A gastro pub named for the Irish author, Lady G's is home to the most important piece of literature in Chicago: set in the dining room’s book-lined walls is a 50-page drink bible filled with whiskey flights.

Sean Cooley is Thrillist's Chicago Editor, and wishes Pizza Hut would keep giving him free pizza for reading as an adult. Follow him @SeanCooley.

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1. Old Fifth 1027 W Madison St, Chicago, IL (West Loop)

Old Fifth is a pizza-slinging pub that's got some of the oldest whiskey in the known world, and some of the newest (read: most innovative) pizzas, like a double-decker one lined with pepperoni.

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2. Duke Of Perth 2913 N Clark St, Chicago, IL 60657 (Lakeview)

The Duke of Perth is serving up pub-style fish and chips, and a whiskey selection that'll blow your mind.

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3. Delilah's 2771 N Lincoln Ave, Chicago, IL 60614 (Lincoln Park)

Delilah's is a neighborhood bar with over 400 whiskeys, located in Chicago's Lincoln Park.

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4. Longman & Eagle 2657 N Kedzie Ave, Chicago, IL 60647 (Chicago)

Longman & Eagle has got it going on. The Logan Square restaurant-slash-bar-slash-B&B is a Michelin-starred destination for upscale American fare, craft beers, small-batch wine, and serious whiskey options (there are over 300 varieties). Nearly half of the menu is under $20, including the signature wild boar sloppy joe, which makes the gastropub a no-brainer for quality and value. Longman has a tiny upstairs inn with six furnished rooms, but be prepared for a loud night given the downstairs bar is open until 3am on weekends.

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5. Drumbar 201 E Delaware Pl, Chicago, IL 60611 (Gold Coast)

Not only is Drumbar one of the sexiest rooftop lounges in Chicago, the 18th-floor bar atop the Raffaello Hotel has a brag-worthy selection of whiskey, scotch, bourbon, and cognac. The sleek spot has a cozy den-meets-gentlemen's club decor with dark leather couches, wood-paneled walls, and a marble bar. During the summer, the seasonal outdoor patio makes it even more of an after-work drinking destination near the Magnificent Mile.

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6. The Berkshire Room 15 E Ohio St, Chicago, IL 60611 (River North)

The Berkshire Room is a whiskey bar serving cocktails from Prohibition-era medicine bottles, a 1940s-inspired menu including bison tartare, and drinks with crazy ingredients, such as tobacco smoke (?!).

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7. The Monkey's Paw 2524 N Southport, Chicago, IL 60614 (Lincoln Park)

It's been said that a monkey's paw has the power to grant wishes, which probably would have resulted in fewer pawless monkeys, if only they understood the concept of "wishing". Thankfully, your wish for an entire wall of whiskey has been brought true by the team at The Monkey's Paw, a new grub-pub handsomely stocking nearly 50 single malts and other fine browns behind a meandering cork bar that's flanked by a dusty-booked library, which operates on the Dewar's Decimal System.

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8. Twisted Spoke 501 N Ogden Ave, Chicago, IL 60642 (West Town)

In case the exterior motorcycle art and bike handlebars on the front door didn't tip you off, Twisted Spoke is a biker bar. The West Town hangout is beloved by Chicagoans of all stripes thanks to a massive selection of whiskey and beer, legendary Bloody Mary menu, rooftop garden, and sinister bites like barbecue nachos and fried jalapeño poppers. Of all the things that make Twisted Spoke stand out though, it's the weekly Saturday night "Smut and Eggs," when you can order breakfast food and watch porn. Um.

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9. Untitled 111 W Kinzie St, Chicago, IL 60654 (River North)

Tucked behind inconspicuous doors that are literally untitled, this lounge is a nod to the Prohibition-era supper clubs, featuring libations, small American bites and a stage where acts range from Motown and funk to local bands and DJs. Untitled is one of Chicago’s top whiskey bars, and undoubtably the best bar for live music in River North. Check out its weekly burlesque show—admission is totally free!

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10. Lady Gregory's 5260 N Clark St, Chicago, IL 60640 (Andersonville)

From the folks behind similarly literary-themed Irish sibs Beckett's and Wilde, Lady Gregory's intricate dark wood moldings and book-lined library (complete with a portrait of its namesake) provide a fitting backdrop for sampling their 300-strong whiskey list. Floor-to-ceiling windows beckon you inside, and once you realize you're in an Irish pub with a passion for farm-to-table, sustainable, local ingredients, you'll probably stay for dinner.

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