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,