Chicago’s Top Cocktail Bars

Marcin Cymmer/Courtesy Vol. 39

The best places in Chicago to cozy up to the bar and grab a drink.

Chicago is a city that is home to every type of bar you can think of. There are plenty of historical places to get a drink, like Twin Anchors and Marge’s in Old Town, or Coq d’Or in Streeterville. And being a city of multiple championship-winning teams, there is certainly no shortage of sports bars where you can watch the Bulls, Cubs, etc., drink a few pints of beer, and maybe eat some wings while you’re at it. But Chicago is also a city of great cocktail bars, from tiki-themed and retro-leaning spots to small and minimalist bars serving complicated cocktails, to whiskey-centric meccas with vintage spirits cabinets that bottle collectors have only dreamt about.

Chicago is a large city with many different neighborhoods, each with its own defining characteristics. But it seems that no matter where you travel nowadays, a good drink is not far off. Well, almost everywhere—there are actually dry precincts in Chicago, areas where voters have chosen to ban the sale of alcohol. There are various reasons why people might choose to go this route, and some of them make sense. But for those looking for a stiff drink, a light aperitif, an exotic tiki concoction, or a well-made simple classic like an Old Fashioned, Chicago’s got you covered. Here are ten of the best cocktail bars in Chicago to drink at right now.

Billy Sunday


Courtesy Billy Sunday

Billy Sunday was a baseball player turned preacher who was also a strong supporter of the Eighteenth Amendment, better known as Prohibition. This Chicago bar of the same name would certainly not sit well with him, with its vintage spirits library and colorful cocktail menu. There are classics, of course, like the Penicillin and Old Fashioned, both skillfully composed. There are also four draft cocktails to choose from, including the Octli that mixes tequila, sweet woodruff, and wormwood, the herb once thought to give absinthe its hallucinogenic properties. Some standouts you won’t find anywhere else include two shots of Cynar (1970s and contemporary) called Something Old, Something New, and the Box Lunch made from the Italian liqueur Genepi, goat’s milk, and oatmeal spices.

The Whistler


Courtesy The Whistler

There’s as much focus at The Whistler on live music and art as there is on the cocktail menu, which changes so frequently the bar posts a daily picture of it on Instagram so you can keep track. DJs spin hip-hop, soul, and r’n’b, while musicians take the stage to play everything from jazz to rock to country as guests sip on cocktails that often reflect the season. This fall featured the Buck Hunter, a mix of corn toasted scotch, butter-washed Falernum, and pumpkin puree. The simpler but still complex Girl Out West was a smoky melding of mezcal, Cynar, lemon, and curry. If you are thinking of stopping by, check out the code of conduct on the website that aims to make sure everyone feels welcome, regardless of race, gender identity, or belief system.

Sportsman’s Club


Courtesy Sportsman's Club

Sportsman’s Club was originally a hangout for Chicago’s Polish immigrants. The current bar, which opened in 2013, retains its old-school feel with Polish beer on the menu and a clubby vibe complete with taxidermy hanging on the walls. But it’s now more of a modern cocktail oasis, with an amaro machine serving a blend of different labels, and a carryout liquor program so you can take a bottle to go. The cocktail list changes daily, with the bar staff deciding on what to serve, how to make it, and which ingredients to use. The current categories are: Sportsman’s Cocktail, Single Barrel Manhattan, Low Life, and Amaro Machine shot. The best way to find out what’s in these drinks is to stop by and try one for yourself.

The Drifter


Courtesy The Drifter

In the basement of the Green Door Tavern you’ll find The Drifter, a bar that also features nights with horror movie screenings, fortune cookie menus, and various other types of live entertainment that could include burlesque, sword swallowing, or all of the above. The drinks menu changes daily, with several cocktail choices drawn from a stack of Tarot cards on which each one is listed. A recent example was called More Bees Please, made from gin, wildflower honey, lemon, and dry curacao. Come to The Drifter for the drinks, stay for the show.

Three Dots and a Dash


Aesthetiica Photography/Courtesy Three Dots and a Dash

Another Chicago tiki option is Three Dots and a Dash. This celebrated bar uses fresh fruits, cold-pressed juice made in-house, and an impressive range of spirits in a wide-ranging cocktail list served in a very convincing tiki setting. The menu details where each drink’s inspiration came from—for example, there is both a Trader Vic Style Mai Tai (from Oakland, CA) and a Hawaii Style Mai Tai (Royal Hawaiian Hotel, Waikiki), each using different spirits and fruit choices. Even drinks like an Old Fashioned are given a tiki twist, combining barrel select bourbon with rum and honey. The group cocktails get a bit theatrical; the Treasure Chest mixes rare rum in a chest overflowing with dry ice smoke, for example. There’s also a smaller bar within the bar called The Bamboo Room, where you’ll find a menu focused on daiquiris and other classic tiki drinks.

Vol. 39


Marcin Cymmer/Courtesy Vol.39

If you’ve ever dreamed about a six-martini flight consisting of one-ounce pours of different styles, check out Vol. 39 in the Kimpton Gray Hotel. The atmosphere here is elegant, with cases of vintage books and leather couches setting the scene. Beyond the martini flight, there are eight different types of Old Fashioned, each made with a different base spirit, updated versions of classics like the Prescription Sazerac made with rye, Armagnac, and smoked demerara, and a bunch of new-school creations. Also, a Vintage Reserve menu is available now, comprised of five expensive cocktails made with spirits from the 1950s to the 1980s. For a taste of boozy history, splurge on the Dusty Bottle Black Manhattan, a combination of 1958 Jim Beam Bonded and 1970s Amaro Averna.

The Violet Hour


Isabelle Langheim/Courtesy The Violet Hour

The Violet Hour is located in Chicago’s Wicker Park neighborhood. Stop by this dimly lit cocktail lounge to try out a menu that rotates with the seasons and is divided into shaken, stirred, and classics sections. The Blue Ridge Manhattan adds a little smoky single malt scotch to punch up the drink’s flavors, while the Spleenless Bastard is based around apple brandy, one of the oldest American spirits. There are some house rules to follow—don’t order a Budweiser, or any light beer for that matter, and definitely don’t ask for a Cosmo. Monday through Thursday you can chase the green fairy at the absinthe happy hour from 6pm to 8pm.

Hush Money at Mordecai


Courtesy Folkart

The team behind Billy Sunday opened this new American restaurant in the Zachary Hotel across from Wrigley Field. Before, after, or instead of a meal at Mordecai, head upstairs to Hush Money, where you’ll find some baseball-themed drinks (of course) like the Stolen Pennant, made with rum, pineapple and muscovado, and the simple Tiebreaker that combines tequila with Aperol and soda. Also check out the vintage spirits menu, with a staggering array of dusty bottle bourbon selections from decades past, European export versions of time-tested brands, and labels that disappeared from the market years ago.

Kumiko

Kumiko, in Chicago’s West Lake neighborhood, has a bar program focused on Japanese flavors and spirits. This means that an Old Fashioned is made with the blended Japanese whisky Iwai Tradition instead of bourbon, mixed with shochu and French fortified wine. Nikka Coffey Gin is the main ingredient in the Sea Flower, served with a rim of something called “ocean dust,” and Haku Vodka is combined with champagne in a drink called Walk Softly. There are also sake flights and a highball menu that uses Japanese whisky, gin, tequila, and shochu. And downstairs from Kumiko, you can enjoy a seven-course omakase dinner at Kikkō—which just received a Michelin star—with beverage pairings that include sake and cocktails, sake and Japanese spirits, and more.

Lost Lake

Lost Lake brings a bit of the tropics to cold Chicago (at least for half the year), with a tiki theme that draws inspiration from the classic Don’s Beachcomber Café. This bar has won various awards for its rum (and rhum) based cocktails, some of which are inspired by classic tiki recipes, others that are completely new creations. Several dark spirits are combined in Feet First in the Deep End, including bourbon, amaro, and Panamanian and Guatemalan rums. The eponymous Lost Lake brings booze and fruit together in a mix of pineapple, passion fruit, Campari, and Jamaican rum. There’s even a bar within a bar at Lost Lake called Stranger in Paradise, where bartenders are encouraged to experiment with concept and ingredients.