Top 5 bars in… Chicago

Regardless of status – whether a destination spot or local watering hole – bars in the Windy City are embracing the good-time vibes, writes Haley Forest.

Chicago boasts a bustling population of quality-driven bars while keeping its Midwest sensibilities firmly in place

Chicago has well established a reputation as a leader in the culinary world. Chefs like Grant Achatz have long been advancing techniques and palates to the edges of our wildest dreams. But on the drinks side, it has been more of a slow and steady progression towards greatness, whereas cities like San Francisco and New York seemed to jump all at once into the new era of craft cocktails.

Filled with boutique products, speakeasies and obscure classics, advanced cocktail cities can exude a sense of exclusivity and pretentiousness – which can make for a less-than-warm entry to the world of nice drinks. Chicago, on the other hand, has managed to grow a bustling population of quality-driven bars while keeping its Midwest sensibilities firmly in place: hospitality infused with a genuine kindness and interest that makes everyone feel instantly at ease.

Bars like Sepia, The Violet Hour, The Drawing Room and Sable set the stage for high-calibre cocktails, but it was the arrival of neighbourhood-focused spots that established a true Chicago charm. Maintaining a vibrant, local feel and an approachable price point, these bars were staffed by bartenders who went the extra mile to build their programmes.

“We saw bars designed or developed to be neighbourhood dive bars with cheap beer and cheap shots of whiskey, but being tended by some talented bartenders,” says Peter Vestinos, president of the US Bartenders’ Guild in Chicago and beverage manager of The Betty and Sparrow.

“The Whistler and Scofflaw were game-changers. They brought craft cocktails in a relaxed neighbourhood environment. It was no longer an expensive, downtown thing.”

The right approach

This kind of approach was right in line with the city’s friendly ethos, and these bars have thrived, developing their own distinct vibe, morphing to be as unique and diverse as the areas of Chicago itself. While these new concepts brought with them a kind of escapism, they always kept true to their roots.

“People get really attached to their neighbourhoods,” says Trevor Albert, who tends the bar at the Broken Shaker. “People are proud of their area and like to celebrate it in its bars. At the Shaker, we want everyone to have a smile on their face. That vibe is everything, with how we make drinks, planout service and conceptualise all aspects.”

The Broken Shaker, the second outpost of the Miami bar located in the Freehand hostel, has created a vaguely tropical feel that fits well within the Chicago scene. Easy-going and vibrant, they imported a sense of the beach without making it contrived. Having only opened in summer 2015, it has already become a hit with locals and visitors alike.

Even as bars have developed more refined concepts, the undercurrent of genuine hospitality runs throughout, allowing guests to relax and enjoy these alternate worlds. Over at The Drifter, located in the basement of The Green Door Tavern, guests have to enter through a bookcase, giving off an initial feel of a speakeasy but with a distinct lack of pomp and circumstance. Almost all the décor has been on-site since the early 20th century, further creating an otherworldly atmosphere for guests.

Partner Liz Pearce says she consciously wanted to make this a place for friends to gather. By adding details like nightly changing menus (printed on and inspired by Tarot cards), stage shows filled with burlesque and oddities, and a nightly ritual of playing ‘Percolator’ by Green Velvet and offering guests shots from a trumpet kept behind the bar, the team maintains an element of fun and whimsy that keeps everyone grinning.

“I think it’s exciting to serve a quality product and it’s a powerful feeling when you find a better way to do something or consume something,” says Alex Renshaw from TheDogma Group, a hospitality consulting company.

“Eventually you realise that you know all this stuff because it is your job to do so, and not your customers’. Then you try to make it approachable instead of making your customer feel like an asshole for not knowing how to read your menu. It all creates an environment to make people feel cool, or to have a cocktail make you feel something instead of just taste good.”

Click through the next few pages to discover our pick of the top five best bars in Chicago.

The Drifter