Can you get a good cocktail in Chicago? You bet your VHS copy of Ferris Bueller’s Day Off you can! get us salivating with some of the best locales and libations in town…

The Windy City has its share of charms, and they easily lure millions of tourists each and every year. From storied professional baseball and football teams to excellent food and architecture, anyone unable to enjoy this urban paradise is either lost in another town or simply not trying.

Nowhere is this truer than in the realm of the creative cocktail, which is only fitting given Chicago’s gangster-fueled melees during Prohibition. For the cocktail lover who wants to enjoy the classics along with the cutting-edge, Chicago can more than hold its own. Here are a handful of reasons why any liquor lover should spend as many evenings as possible in Chicago.

The History

Chicago was a hotbed of rebellion against that grand experiment known as Prohibition, and that rebellion took on many forms. Speakeasies were abundant throughout the city for those willing to skirt the law in order to wet their whistles, and some of the original ones are still in operation even today. Of course, the speakeasies had to get their booze from somewhere, which is why gangsters and violence were synonymous with Chicago during the 1920s. From Al Capone to the St. Valentine’s Day Massacre, the public’s ongoing thirst for liquor created an environment of violence that was so bad that 227 gangsters died over the course of four years.

By the time Prohibition was repealed in 1933, many of the remaining gangsters were in jail or were turning their attention to other endeavors, but the look and feel of 1920s Chicago remains in many places — including O’Hare’s Bubbles Wine Bar, which is one of the best airport bars in the country.


Experience some of the Roaring Twenties at this swanky restaurant and bar located in the West Loop. Jazz, Michelin-rated food, and a stellar atmosphere set the stage for expertly crafted and poured cocktails in handsome glassware. While some of the bars on this list are best enjoyed during the cocktail hour only, Sepia’s exceptional food makes this destination one that should last through dinner.

Bernard’s Bar

Set within the Walkdorf Astoria, this bar is vibey, tucked away, haute, and filled with stellar drinks and food. While the cocktail menu is small, it caters well to the classics, while indulging a few tasty and thoughtful twists.

Of course, since it’s a full bar with excellent bartenders, you can order whatever you’d like, but the whiskey-based drinks on the menu are superb. Small plates and charcuterie are available on the weekends, so you can drink a couple of cocktails with some snacks and still have your wits about you enough to head out to dinner.

Punch House

Kitschy, vintage and delightful, Punch House feels more like your grandparents’ basement than it does a classic speakeasy, and the name fits the menu — a rotating list of eight different house punches can be ordered by the glass, the carafe, or the bowl, and every one of them includes classic and inventive ingredients that bow to the five essentials of a classic punch: strong, weak, bitter, sour, and sweet. For those uninterested in the “punch,” there are other libations available; however, skip the negroni for one round, and consider going all in with what they’re known for.

The Barrelhouse Flat

A newcomer on the scene, this Lincoln Park bar already feels like a staple. Cozy booths and soft but luminous lighting accent the feel and the drinks at Barrelhouse Flat. A lengthy list of classic cocktails is complemented by another menu of house experiments that are adventurous and seasonal. For the cocktail aficionado, who wants to experience a world of flavors and liquors that have rarely been brought together, this bar affords a rare treat.

Juliet and Romeo Cocktail

Not only does Chicago boast some excellent bars, but the city’s bartenders have also created some iconic cocktails that any visitor to Chicago should take in. One such concoction is the Juliet and Romeo at The Violet Hour. A blend of Beefeater gin, Angostura bitters, mint, cucumber, rose water, and lime, you can almost taste the unrequited love and heartbreak in it.

In The Rocks Cocktail

The Aviary is the home to one of the most interesting cocktails in all of Chicago. While its ingredients change pretty regularly, it’s the experience of In The Rocks that keeps people coming back for whatever new version is currently on the menu. Basically, your drink is encased in a large, hollow ice cube. You break it with a small slingshot, so the liquor spills over the icy splinters in the bottom of your glass. Then, you drink up.

From its iconic history to its ongoing love affair with making booze a priority, Chicago truly is a city worthy of exploration for any cocktail lover looking for a getaway.

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