While famously home to notorious bootlegger, speakeasy boss and career gangster Al Capone, Chicago’s drinking culture has come a long way since Prohibition.
Bringing it up to date—hot on the heels of the city’s transformation into one of the country’s culinary capitals—are cocktail pioneers like Toby Maloney and Market-Fresh Mixology author Bridget Albert.
This new generation of skilled and talented bartenders has developed a reputation for hard work and creativity. And the sheer quality, ambition and diversity of establishments makes Chi-town a must-visit for anybody who appreciates good drinks.
Celebrity chef Grant Achatz’s eagerly anticipated restaurant and bar recently opened its doors to great acclaim. While his world-class restaurant Alinea has always treated its guests to a unique cocktail experience, The Aviary and Next bring further innovation to the field of mixology.
What to Drink: Blueberry
Without a doubt, Bar DeVille is my favorite neighborhood bar in Chicago. It has a laid-back atmosphere, and whether you’re drinking whiskey, beer, tequila shots or a Ramos Gin Fizz, you’ll have a good time.
What to Drink: A shot of Jeppson’s Malört Liqueur and a good beer
Big Star is all about whiskey, tequila, beer and tacos. (Is there a better way to spend an evening?) Housed in an old garage, it’s definitely one of Chicago’s coolest hangouts. No surprise, since it was opened by the people behind local institutions Avec and Blackbird.
What to Drink: Sarsaparilla Springs (Buffalo Trace Bourbon, AJ Stephans Root Beer)
Boka is known for its seasonally driven contemporary cuisine. Head bartender Ben Schiller is a key part of the culinary team, and his short but inspired menu pairs well with executive chef Guiseppe Tentori’s dishes.
What to Drink: Old Money (Black Maple Hill Bourbon, Aperol, walnut liqueur, Angostura Bitters, allspice liqueur)
Consultants the Tippling Bros., AKA Tad Carducci and Paul Tanguay, have been working with the Mercadito restaurants in New York for some time. They also set up the bar underneath the group’s Windy City outpost. Double A has an extensive list of original and classic concoctions.
What to Drink: Cheeky Cheeky Boom Boom (Absolut 100 Vodka, elderflower liqueur, strawberry, lemon juice, vanilla sugar)
A James Beard Award semifinalist and the winner of NBC’s On the Rocks bartender-competition series, Charles Joly has pulled together some of the town’s best mixologists. The Drawing Room (pictured above) is an industry leader, which combines modern technique with perfectly executed historic elixirs.
Billed as a “continental tavern,” the warm and inviting Hubbard Inn delivers with authentic European dishes and an extensive drinks menu. Ben Tozer will have you sipping fine cocktails and sampling an excellent range of ales and lagers. And then there are the regal monkey portraits on the wall—pay a visit and it will all make sense.
What to Drink: Hubbard Rose (Evan Williams Hubbard Inn 2001 Vintage Bourbon, Damascan Rose Elixir, port, lime juice)
The bar at Sable is a Jacques Bezuidenhout production. With his training and education in place, he turned the day-to-day running of the establishment over to the very capable Mike Ryan. It boasts an elaborate spirits list that takes up 32 pages, with an additional eight pages of cocktails.
Aussie Josh Pearson brings his bartending knowledge and passion to one of Chicago’s top eateries. Order one of his well-thought-out original concoctions made from a range of exotic and fresh ingredients.
What to Drink: South x Southwest (Olmeca Altos Reposado Tequila, St-Germain, rosemary, lemon juice, moscato d’Asti wine, old fashioned bitters)
Toby Maloney has worked with the best in the industry. He has brought all his experience and skill to The Violet Hour. You’ll enjoy flawlessly executed classics in an elegant and dimly lit space with a traditional speakeasy feel.
What to Drink: Juliet and Romeo (Beefeater Gin, mint, cucumber, rose water)
Looking for more great watering holes? Check out our bar guide for the best bars in the world.
Simon Ford is an award-winning bartender and director of trade outreach and brand education for Pernod Ricard USA. He is also a Liquor.com advisor.