Where to Drink Chicago's Fanciest Cocktails

Chicago’s cocktail rooms offer the full spectrum of moods, from the cheery Lost Lake to the fancifully inventive Aviary to the deadly serious (and seriously romantic) Violet Hour. When the drinks are served up, you’ll usually get something pretty delicious. Judging by the city’s range and quality of cocktail bars, you could even make the argument that Chicago is the equal of New York on mixed drinks, and without the occasional whiff of snarky service.

Cocktails are done with a particular local spin in Chicago, a bias toward challenging aromas and sensations. From their hot dog toppings to their taste in liquor, Chicagoans can be more daring around spicy and bitter flavours than other Americans. Maybe it’s something to do with the city’s Italian, German and Mexican influences? Whatever the reason, the typical Chicago cocktail is powerful, usually more bitter than sweet, and above all well-crafted. Here are some of Billy’s favourite spots to stop for a sip.

The Violet Hour
Patrons first discovered the unmarked door and pulled back the velvet curtains here in 2006, making The Violet Hour the dean of the scene in Chicago and an influential pioneer in the worldwide movement to bring back quality cocktails. Classy bars had been defunct in North America for so long that The Violet Hour felt the need to spell out certain rules of decorum for an unaccustomed generation (“no baseball hats,” for example). The rules still stand; talking on a cellphone or even ruining the lighting by checking it is considered déclassé here. Sink into your throne-like chair and focus instead on the drinks, which are exquisite. We especially enjoyed the “fox hunt” (Pimm’s, gin, Cynar, Peychaud’s bitters) and the “blame Spain” (rum, cherry bitters, madeira; and so that you don’t have to pick up your phone to look it up: Yes, Madeira actually belongs to Portugal, but oh well).

1520 N. Damen Ave., 773-252-1500

Lost Lake
Tiki bars are slowly resurfacing, and the youthful crowd piling onto this little rum-soaked island proves the trend has truly reached the shores of Chicago. Tiki means floral patterns, South Pacific iconography (totally fake; hatched in the imaginations of mid-20th-century Americans) and heavy-gauge rum drinks. Rather than serve up the same old zombies and mai tais, Lost Lake came up with its own tiki repertoire. These cocktails are by no means as frivolous as the crazy garnishes may lead you to believe: As per tiki tradition, most of the drinks are delicious, and contain enough hooch to blow a pirate sideways. Be especially cautious around the big boozy punch bowls, which are delivered to your table with long straws for sharing. Soak some of it up with snacks from the Chinese takeout next door, which the servers will handily deliver to your table. (May the beef dumplings in broth be your sunken treasure.)

3154 W. Diversey Ave., no phone

Courtesy Lost Lake

Lost Lake

Sportsman’s Club
In late 2013, local bar industry veterans took a Polish neighbourhood bar and filled it with taxidermied heads and old chandeliers while keeping the checkerboard tables and the vintage back bar (a beautifully Art Deco-esque wooden number). They called the resulting décor “French hunting club”; anyone else would just call it “hipster,” and a well-dressed twenty- to fortysomething clientele came pounding on the door in due course. The cocktail menu changes daily, and the (bargain!) $10 drinks are described simply by ingredients – for example, “rye, fernet, coffee.” Just say “the rye cocktail” or “the apple brandy cocktail” and staff immediately get to work. Sportsman’s Club’s bartenders are human marvels, the technically proficient sort who can keep the ever-changing menu memorized while making a different drink with each hand. As is the style in today’s Chicago, the cocktails are on the strong and bitter side, and there’s even an amaro machine dealing out quick chilled shots. If the weather’s nice, finish your mixed drinks and enjoy a relaxed beer on the back patio.

948 N Western Ave., 872-206-8054

Billy Sunday
This Logan Square bar was named for an outfielder for the Chicago White Stockings (among other 19th-century baseball teams), who later became a famous evangelist and proponent of the temperance movement. The hard feelings between bar folk and Billy Sunday are ancient history, but a different kind of bitterness still reigns here: The peculiar specialty of the house is a jaw-droppingly long list of rare and vintage amari, with amaro being a category of herbal Italian after-dinner liquors. They’re often aggressively bitter. Watch out in particular for the subtype called fernet; it’s a real lip-puckerer. Billy Sunday is for fans of odd and challenging flavours generally, from the bar snacks (anyone for chicken liver and crackers? Actually quite tasty) to the cocktails. The “Victorian,” for example, is an advanced cocktailer’s cocktail, delivering a triply bitter threat of fernet, another amaro, and wormwood bitters, softened only by the hint of malt in the genever (that’s Dutch gin). Things get weirder: The “lunch box” consists of goat’s milk, “oatmeal spices,” genepi (a rarely seen French mountain liqueur) and palo cortado (not just sherry, but a tasty type of sherry you don’t see every day). Booze geeks assemble!

3143 West Logan Blvd., 773-661-2485

Courtesy Billy Sunday

Vintage liquors are a specialty at Billy Sunday

Chicago’s most talked-about cocktail bar is an experience, and much of it is disorienting. While Aviary does take walk-ins, it’s wiser is to book tickets in advance, just like at Grant Achatz’s parent restaurant, Alinea. Packages start at US$20 for an à la carte visit; things will escalate quickly from there. You start off in a waiting area where you can watch Achatz’s clockwork minions afoot in a gleaming kitchen – not a bar, mind you – separated from you by a metal cage. How about a “Snickers” bar made from foie gras and a shot of pineapple juice while you wait? The lighting is high for a cocktail bar, the better for you to witness the true exotica on offer, replete with sprays, flavoured vapours and flames. Jellied elements are transformed from liquid to solid using molecular trickery. The presentation can be odd (for example, a cocktail sealed in a plastic bag to keep the aromas in) and the flavour combinations even odder, though for the most part they really work – who knew bourbon, madeira and caramelized onion were delicious together? Aviary is a bar to impress and be impressed, though not necessarily one where you can unwind. Staff frequently pop up to your table to announce and explain the freshest novelty. The Aviary experience is more about Aviary than it is about you, so be prepared to pay attention, and keep in mind that any client meetings are apt to be derailed. 

955 W Fulton Market, no phone


1. The Violet Hour; 2. Lost Lake; 3. Analogue; 4. Sportsman's Club; 5. Billy Sunday; 6. The Aviary.

Published Friday, October 9th 2015

Header image credit: Courtesy Eden Laurin/The Violet Hour



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