1. Old Fifth1027 W Madison St, Chicago
2. Duke Of Perth2913 N Clark St, Chicago
3. Delilah's2771 N Lincoln Ave, Chicago
4. Longman & Eagle2657 N Kedzie Ave, Chicago
5. Drumbar201 E Delaware Pl, Chicago
6. The Berkshire Room15 E Ohio St, Chicago
7. The Monkey's Paw2524 N Southport, Chicago
8. Twisted Spoke501 N Ogden Ave, Chicago
9. Untitled111 W Kinzie St, Chicago
10. Lady Gregory's5260 N Clark St, Chicago
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.
The Duke of Perth is serving up pub-style fish and chips, and a whiskey selection that'll blow your mind.
Delilah’s is a truly remarkable place disguised by the facade of a dreary, punk rock dive. Monday through Saturday, it’s an above-average Lincoln Park hangout with some 200 beers, 750 whiskeys, music, and a rotating art gallery featuring local artists. But the real magic happens on Sundays during football season, when Buffalo fans unite in the narrow dive to shout at TVs showing their beloved Bills. This is no average football viewing, this is serious -- I’m talking tears, dolphins engulfed in flames during Miami match-ups, and bear hugs in victories and losses alike. With every touchdown, a devoted fan buys a round of shots for the bar, and every surface is constantly covered in cans of Labatt Blue. Game days at Delilah’s are not for fair weather Bills (or Sabres) fans, nor for anyone shouting anything other than “Let’s Go Buffalo!”
Longman & Eagle, the Michelin-starred gastropub in Logan Square, has an exclusive whiskey selection (clocking in at over 400 labels), a craft cocktail menu, and an extensive beer list all fit for the most pretentious of drinkers, in the least pretentious of atmospheres. Longman takes a flavor-forward, honest approach to eating and drinking, and because it doesn’t accept reservations, there is always a wait for brunch, happy hour, and dinner alike. (And it is always worth it.) While whiskey may be king, the regional American fare has just as much to offer, hence the Michelin star. The menu changes often, but expect anything from beef tallow beignets and veal brains to wild boar sloppy joes, chicken and waffles, and a burger that, if you know what's good for you, you will order.
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.
Inside the Acme Hotel in River North, The Berkshire Room is an old-time cocktail lounge that harks back to when the hotel was called The Berkshire Hotel from the 1920s to 1950s. The drink selection puts a heavy emphasis on barrel-aged cocktails, but the real stunner is the Dealer's Choice, essentially an off-menu cocktail based on your choice of spirit, flavor profile, and glassware. The space is dark and cozy with black-and-white tiled floors and a long, glossy bar.
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.
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.
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!
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.