Chicago is without a doubt a whiskey town. Ask a local where to find the best selection, and you'll likely be faced with a long and detailed list of options. From dives like Delilah's to more upscale joints like Longman & Eagle, one can find a good place to down a dram in almost every neighborhood.
Yet bars with new liquor focuses are also opening with each passing month, making it easier to find the best spot for rum, gin, tequila, and even Italian amari within city limits. Here are some of the best spots to explore, whether you want to sip a spot of rum, taste your way through a flight of agave spirits, or sample some homegrown vodka.
For Whiskey: Delilah's
One of Chicago's most renowned spots for whiskey with an attitude, Delilah's has rocked a great selection of over 600 whiskies since 1993. The small Lincoln Square "rock n' roll booze emporium" is divey without being too disheveled, and the bartending staff are friendly without being in-your-face about customer service. With $3 daily specials ($4 for mixed drinks), you'd be hard-pressed to find a more affordable place to throw back a shot of Maker's or Jim Beam before a night on the town, but their vast selection also plays host to more prestigious offerings as well; the bar stocks Scotch from over 70 distilleries, including some rare single cask offerings from private bottlers. They also team up with a different distillery every year to make a new whiskey for their anniversary parties; last year they collaborated with revered Compass Box Whisky on a bottling that is now available internationally.
More Whiskey: Fountainhead
This welcoming Ravenswood/Lincoln Square gastropub is known for its great craft beer selection, but what most people don't realize is that their whiskey collection is also extensive. 10 pages of the 29-page house drink menu are dedicated to a wide variety arranged into sections based on origin, including bourbon, American whiskey, Scotch, and Irish whiskey. They also have a special selection of rare Scotch selected by the Scotch Malt Whisky Society in Edinburgh, including Cask No. G3.3, a 26-year-old "Curious But Good" whisky aged in a bourbon barrel, and the 22-year-old Cask No. 30.70 called "Venus in Furs," whose quirky flavor notes include "well-matured Dundee cake washed down with black currant and cordial," and "horse shoes and fresh mud." It's a fun list to explore.
While the mahogany-clad bar is warm and cozy in the winter (with plenty of natural light, something not all gastropubs enjoy), one of the biggest perks is the rooftop patio, which opens for sunshine-hungry patrons as soon as the weather warms up. And if their vast selection of whiskey and friendly ambiance isn't enough to please, the bar also hosts regular whiskey education sessions and tastings in the Barrel Room.
For Gin: Scofflaw
Even before Scofflaw opened their doors in March 2012, the crew responsible for the Logan Square bar (alumni of The Whistler and Boiler Room) knew they wanted to team up with a local distiller to make a house liquor reflective of their focus—gin. The Scofflaw Old Tom Gin was created in collaboration with North Shore Distillery. Co-owner Danny Shapiro says it's "a bit higher proof than the others on the market (45% ABV / 90 Proof) and contains a subtle floral note due to the inclusion of osmanthus blossoms."
But the house Old Tom is merely one of over 80 bottles of gin stocked at the cozy antique-clad bar. Traditional London Drys share shelf space with Dutch-style Genevers and a broad selection of New American gins, like the lavender-forward Waterloo from Treaty Oak Distilling in Texas, and a local gin from Few Spirits that boasts a lemon peel and vanilla profile. A house cocktail list also explores the versatility of Mother's Ruin, with a small selection of drinks listed at an affordable $8 each. Warm up to the fireplace in the slightly disheveled Victorian-style back room with one of their well-balanced gin cocktails for one of the most relaxed, intimate drinking experiences in Chicago.
For Vodka: CH Distillery and Bar
There is something truly special about drinking a spirit from a barstool within eyesight of where it was created. While several new distilleries have opened in Chicago in the last year that also have in-house cocktail bars and tasting rooms, CH Distillery and Bar easily has the most captivating space. They also happen to make outstanding vodka.
Made from red winter wheat and rye grains sourced 50 miles from the city center, CH mills, ferments, and distills the grain in-house, which is pretty rare. Not many distilleries make vodka from scratch. The spirit is soft and slightly sweet upon first sip, then evolves into a slightly dry and almost peppery finish. Try it the "traditional" way at the bar, with a slice of rye bread and pickles, for the full effect.
For Rum: Three Dots and a Dash
There are few bars in Chicago that provide more of an escape from the real world than Paul McGee's Three Dots and a Dash. Between an on-point tiki atmosphere, extensive list of Polynesian-inspired cocktails, and impressive back bar selection, this whimsical bar is one of the best places in the entire country for discovering and exploring rum.
With over 255 bottles hailing from a wide geography including Martinique, Venezuela, Costa Rica, Nicaragua, Bermuda and 21 other exotic locales, finding a pleasing style or vintage would be difficult without the help of the knowledgeable and friendly staff. Ask about some of the house's most exclusive bottles, like the Black Tot Rum, which was last distributed to the British Royal Navy on July 31, 1970 or the Dewar Rattray Caroni 15 Year, a 15 year old rum from a defunct distillery in Trinidad. Overwhelmed by the sheer volume and quality of choices? The bar will begin offering flights soon to help customers taste through a spectrum of styles, ages, distillation methods.
For Tequila: Mercadito
Mercadito offers a thoughtful selection of tequila and an upscale Latin vibe to match. The menu features over 60 options ranging from $9 to $50 per serving, and is appropriately split up into the various types of tequila—blanco, reposado, anejo, and extra anejo. Cousin spirits mezcal and sotol also have a place, with a small but considered selection.
When it comes to cocktails featuring tequila, you're not limited to Margaritas and Palomas. The contemporary list, determined by the famous drink slingers the Tippling Brothers, features inventive and thirst-quenching concoctions like the Little Market ($11.50), a splash of sunshine with pineapple juice and warm guajillo chili spicing up the oaky Olmeca reposado, and El Pirata ($8.50), a spunky twist on your average Michelada with pineapple juice replacing the standard tomato, and Negra Modelo complementing a crisp Cazadores blanco. Looking to avoid the busy upstairs rush? Check out Double A, the downstairs bar that features great weekly specials on drinks, and regularly hosts special tequila-related events.
For Other Agave Spirits: Masa Azul
One of Chicago's best hidden gems, Masa Azul is a small but upscale Logan Square restaurant and bar with a focus on hand-selected Mexican spirits. While they have an excellent selection of tequila, the real stars at Masa Azul are the other agave spirits—mezcal, sotol and bacanora. Partner Jason Lerner takes special care to work with distributors to find high-quality small-batch agave spirits for the roster, which rotates often depending on what unique producers he believes are worth showcasing at the time. The list often includes hard-to-find bottles that not many other bars fight to acquire, like the Ocho Cientos Sotol and the Cielo Rojo Bacanora from Sonora.
You don't need to be an expert before you arrive: the menu offers a brief history of each spirit and other helpful tips for those new to tequila's agave cousins. Flights ranging from $15-30 allow customers to sample a wide range of ages and styles. Agave is also celebrated on the list of classic cocktails, where mezcal or tequila are typically subbed into traditional recipes. Try the Oaxacan Old Fashioned, which features mezcal joven, tequila reposado, agave, mole bitters and Angostura. It's a sultry, boozy exploration of everything that makes aged agave spirits shine.
For Local Spirits: Watershed
Finding local spirits on the shelves of Chicago bars usually doesn't pose too much of a hassle, but if you're looking for the best place to drink your way through a portfolio of locally-made booze, River North's Watershed is the place to visit. The intimate "parlour room", located underneath the team's popular Champagne bar Pops for Champagne, boasts an entire menu of spirits and craft beer from around the Great Lakes region. From Wisconsin vodka to Michigan gin and Chicago's mouth-puckering favorite Malört, the menu lists liquors by category and includes the state and distillery of origin for each, making it easy to navigate through the options.
If you're not one to sip a spirit neat, they also offer a hearty selection of house cocktails ($10) made with the same crop of ingredients. Try the Phenomenal Genius, a cheeky mix of local New Holland Bourbon, Yahara Bay Coffee, Grapefruit cordial, and 5 Vulture Beer from Chicago's 5 Rabbit Brewery. It's an evolving wash of rich coffee, sweet oak and vanilla, and slightly smoky ancho chili beer—all made within a stone's throw of the bar itself.
For Amari: Billy Sunday
Open just slightly over a year, Billy Sunday rapidly rose to many "best of" lists throughout the country thanks to an inventive list of exceptional cocktails. But what makes this Logan Square bar extra special is the rows of dusty bottles that rest behind the back bar cabinets—a treasure trove of vintage Amari, or Italian bitters.
Thanks to diligent research and a few dedicated contacts in Italy, the bar stocks over 500 different bitter liqueurs (although they are not all for sale). In the menu, or "Good Book" as they call it, there are over 45 different offerings just in the Fernet category, organized by origin location in Italy, and featuring vintages from the 1930s to today ranging from $15 to 45 per sample. The "crown jewels" of the collection, as bartender Alex Bachman describes them, are several bottles from a 1930s collection that were originally marketed as medicine.
An abundance of various other amari are also listed in the book, such as the five different kinds of Rababaro, bottles of Campari Cordial from the 1960s and 1990s, and vintage Genepy from not one, but two different producers. The whiskey selection is also nothing to sniff at, if bitters aren't your thing; the Scotch options range from accessible to very rare, with some decades-old bottles costing upwards of $500 per drink.
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