Chicago Travel Guide

Where to Drink in Chicago Now

Chicago's reputation for top-notch cocktails has been on the rise ever since speakeasy The Violet Hour drew back its plush velvet curtains in 2007, revealing a team of serious spirits enthusiasts who wanted to shake things up in the Windy City. The succession of cultivated cocktail programs that immediately followed continues to be welcomed by locals looking for sophisticated drinks, and Chicago’s finest barkeeps have been hard at work shaking, stirring, and barreling game-changing tipples at a bevy of new establishments, ranging from the single-spirit-inspired venue to the distillery meets drinkery. From River North to Humboldt Park, here are seven new spots for quality drinking in the City of Big Shoulders.


Humboldt Park is the perfect place to find humble prices, and gin haven Scofflaw is no exception. Patrons can sample any of head barman Danny Shapiro’s cocktails or chef Mickey Neely’s small plates for an across-the-board $8—a necessary tab simplifier after those shots of Malort (which is served on tap here). And while 'L' train loyalists might argue against the considerable trek west, the hospitality will surely be worth it—from chocolate chip cookies at midnight to umbrellas and hot cocoa for cold, queued-up crowds.

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What to Order: The Last Light (Letherbee gin, Cherry Heering, house-made ginger syrup, egg white, lemon juice, Angostura bitters).

The Berkshire Room

Dealer’s choice is taken seriously at The Berkshire Room, where patrons choose their preferred spirit, flavor profile, and glassware from the menu before head bartender Benjamin Schiller reaches for any one of the bar’s 400 bottles. The autonomy doesn’t stop there: Guests can ask servers to select a trio of “dealer’s choice” bar snacks based on what they’re drinking. The snack categories—from smoky to herbaceous—are meant to follow those of the dealer’s cocktails (think tobacco onion dip with poppy seed crackers and bourbon-cured olives).

What to Order: Check out one of Schiller’s barrel-finished cocktails, such as the Beginning to End, a concoction of rye, blended Scotch, Benedictine, and Atlantico rum. 

Parson’s Chicken & Fish

In a city where winter is brutal, Parson’s Chicken & Fish does its part in welcoming and celebrating summer—from a ping-pong-ready patio to a frozen drink machine. Head bartender Charlie Schott kept a lighthearted approach when developing the cocktail menu, whose classic riffs range from a mezcal-monopolized Margarita Humosa to a Pompelmo Americano, charged with grapefruit juice and bitters. Come for the drinks, but stay for the food (or vice versa): chef Hunter Moore’s offerings range from raw (oysters) to fried (the same) and pack enough comfort to fuel hours of languid Logan Square loitering.

What to Order: The negroni slushie (Letherbee gin, Luxardo bitters, Martini & Rossi sweet vermouth).

Three Dots and A Dash

There is perhaps no better place to forget the cold temperatures than at Three Dots and a Dash, where lead barkeep and partner Paul McGee turned to Polynesian mixology to create a list of classic and updated tiki tipples. An hours-long vacation presents itself in a full-sensory experience for River North revelers, featuring a thatched grass bar, fishing-rope-slung lighting, vintage tikis, and oversized clamshell cocktail vessels. Even the food is tropically transportive: Luau chips are paired with pineapple guacamole and Fresno chili adorns a green papaya salad.

What to Order: The Three Dots and a Dash (aged rhum agricole, Guyanese rum, honey, falernum, lime, allspice, Angostura bitters). 

Billy Sunday

Yusho chef Matthias Merges ventured a few blocks south for the opening of Billy Sunday, where a “one or more obscure ingredients” attitude informs otherwise familiar fare (think quail egg-bedecked chicken liver and potato gratin with aged gouda). Alex Bachman helms the bar, and his cocktails follow in the same surprising suit: An extensive collection of vintage amari, fernets, and Scotches decorate the bar and enliven offerings like the Amari & Apollinaris, a caged and carbonated bottling of Fratelli Branca Cherry 1960’s, Martini & Rossi, Sola Fernet 1970’s, and mineral water.

What to Order: Feeling like a kid again? Opt for the Box Lunch (oatmeal-spiced goat’s milk, Génépi, and sherry, served in a chilled glass milk bottle with a candy-striped straw).

CH Distillery

Drinking gets educational at CH Distillery, where visitors can tour the grounds to learn about turning Illinois grain into vodka before sampling the product on-site in a Moscow Mule. Beverage director Krissy Schutte serves up a mix of classic and original cocktails using an array of the house-made spirits, from the light (vodka and gin) to the dark (rum and bourbon) and the in-between (handmade limoncello). Meanwhile, executive chef JP Doiron crafts Northern and Eastern European-inspired small plates that help brace Saturday afternoon imbibers for the night’s festivities ahead.

What to Order: The Cease and Desist (CH London Dry Gin, Lapsang Souchong tea, house-made ginger syrup, honey, lemon).

Off Site Bar

The team behind Longman & Eagle give Chicago’s hippest clientele another reason to stampede their premises with Off Site Bar a drinking den suited for the pre-reservation dram and private events. Weekends feature an extended culinary showcase, with sausage and doughnut pop-up shops. If you’ve tried one too many of the venue’s 148 whiskeys, not to worry—one of the six hotel rooms upstairs can shelter you for the evening.

What to Order: The Longman Manhattan (Wild Turkey 101 Bourbon, Punt é Mes, Angostura and cherry bitters).

Nicole Schnitzler is a freelance writer who covers travel, food, drink, lifestyle, and culture. When she is not planning her next adventure, she can be found exploring bakeries, record shops, and drink lists in her Brooklyn neighborhood. She is most comfortable with a pen in one hand and a fork in the other.

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