The 12 Best Cocktail Spots

Bar Deville

Haunt this moody den for its cozy front room, DJ-fueled dance parties, and the delish classic cocktails.

What to order: The Last Word: Beefeater gin, green Chartreuse, maraschino, lime
Find it: 701 N. Damen Ave., 312-929-2349,


The Barrelhouse Flat

An old upright piano sets the speakeasy tone, while a noteworthy beverage list and friendly patrons carry the lively melody.

What to order: Purple Fizz: Sloe gin, soda, grapefruit, lemon, simple syrup
Find it: 2624 N. Lincoln Ave., 773-857-0421,


The Drawing Room

The carefully crafted drinks speak for themselves. If you need help, the knowledgeable staff complies without imparting guilt.

What to order: The Old Man Monk and the Sea: Old Weller 107, Lustau dry oloroso, benedictine
Find it: 937 N. Rush St., 312-266-2694,


The Grafton

At this Celtic haven, partake in an assortment of Irish, American, and Scotch whiskeys, a rotating selection of craft beers, and a folksy Sunday sing-along.

What to order: Fireside Old Fashioned with Buffalo Trace bourbon
Find it: 4530 N. Lincoln Ave., 773-271-9000,


Longman & Eagle

The dark paneling, healthy sprinkling of plaid, meat-heavy menu, and nearly 60 bourbons on hand qualify this restaurant, bar, and inn as the city man’s hunting lodge.

What to order: 1-2 Punsch Swedish: punsch, Leather-bee gin, apricot liqueur, bitters
Find it: 2657 N. Kedzie Ave., 773-276-7110,


The Matchbox

A claustrophobic’s nightmare and a cocktailer’s dream, this 18-seater spins out stiff, cheap, and superb drinks.

What to order: Margarita with egg white and lemon-lime juice
Find it: 770 N. Milwaukee Ave., 312-666-9292,


Maude’s Liquor Bar

This sexy space approaches “refined” in eccentric ways: mismatched chandeliers, tiled walls, wood tables, a $165 shellfish tower, and Miller High Life.

What to order: Maude’s Punch Smith & Cross: rum, egg white, angostura bitters
Find it: 840 W. Randolph St., 312-243-9712,



Award-winning tipples from Violet Hour vet Mike Ryan are reason enough to go, but add in a sprawling 40-foot bar and proximity to the Loop theatres, and why spend Thursday night anywhere else?

What to order: War of the Roses: Pimm’s, Citadelle gin, Chase elderflower, mint, lime
Find it: 505 N. State St., 312-755-9704,


Tiny Lounge

This swanky drink haven crafts a true whiskey sour (with an extracreamy egg white), along with myriad martinis and, as a bonus, to-die-for desserts (order the caramel-ized bananas with créme anglaise).

What to order: Goliath North: Shore Gin 11, green Chartreuse, lime
Find it: 4352 N. Leavitt St., 773-463-0396,


The Violet Hour

Little has changed at this candlelit date spot since its fawned-over opening in 2007: consistent menu and staff, cozy quarters, and long lines.

What to order: First Snow: Herbsaint, aquavit, egg white, lemon sugar, peppermint water
Find it: 1520 N. Damen Ave., 773-252-1500,



The drinks at this decidedly un–River North faux speakeasy include mainly Midwestern spirits, while the overstuffed leather couches add to the windowless parlor’s intimate appeal.

What to order: Natty Gann: FEW gin, lemon cordial, Leopold Alpine liqueur, bitters
Find it: 601 N. State St., 312-266-4932,


Weegee’s Lounge

The low-lit space specializes in classic cocktails. Its dark corners and hushed tones are perfect for an intimate date—or you can always play some shuffleboard in the back.

What to order: Aviation: City of London gin, creme de violette, maraschino
Find it: 3659 W. Armitage St., 773-384-0707,



2 years ago
Posted by mikejaz2

re: The Drawing Room (goes for all)...If I'm going to one of these places, and paying top price for top-shelf liquor and good service, they BETTER impart advice to me without guilt...eye rolling, ironic smirks or any other BS. I'm there to drink, and not be condescended to...

12 months ago
Posted by ZackmoKahn

Totally bummed that Maria's Packaged Goods did not make this list! It deserves at least an honorable mention.

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