Chicago’s Finest Bars: Where to Drink in the Windy City Right Now

The team behind West Loop fine-dining sensation Oriole runs this modern cocktail lair, where mid-century interiors are accented with intricate Japanese woodwork. Creative director Julia Momosé describes it as “a cocktail party with the world’s best hors d’oeuvres.” The restaurant’s Japanese-style drinks—designed to showcase ingredients such as sake and green tea—and small plates were instant hits after it opened doors in 2018, even earning Kumiko a mention as one of Time’s Greatest Places in 2019.

Recently named the best bar in Chicago by the Jean Banchet Awards, The Alderman might be the hottest one in town—and not just because there are just 16 seats inside its speakeasy-esque confines. The dark, moody bar is an ideal location for sipping on something strong, and luckily, drinks from award-winning mixologist Lance Bowman promise a combination of classics with twists. Opt for The Alderman’s spicy spin on a manhattan, made with chai vermouth, or an original creation, such as the Woods + Whimsy, a campfire-inspired cocktail that blends bourbon, smoked tea sugar oil, truffle, and house bitters.

Channeling Miami, Broken Shaker is tucked away in the back of the Freehand Hotel. But don’t let its small size fool you—this tropical bar packs a punch. As do the drinks, which evoke that beach vacation you’ve been lusting after. Try a Seaweed Swizzle with vodka and rosé-seaweed cordial, or go for a spirit-free concoction, which might include a mocktail featuring pineapple, honey, and lapsang souchong smoked tea.

How many beers on tap are too many? For Centennial, the limit does not exist, reflected by a prolific selection that includes over 50 types, from malty maibocks to fruity sours. The rustic, two-story bar also has a menu of bottled and canned beers. As an added bonus, all the food here is listed with a suggested beer pairing—don’t miss the house-smoked ribs and Bavarian pretzel with an amber ale.

When chef Mark Steuer decided to break out on his own with a concept that honored his roots, he settled in West Town with a modern beer hall that serves Southern and German cuisines. The results feature a delightful mash-up of a menu with dishes such as cornmeal-crusted catfish, spaetzle, and Riesling steamed mussels, plus an extensive beer list that showcases plenty of German imports—served in a boot, if you’d like.

For that vintage cocktail experience, head to Gibsons, where the ice-cold martinis are made by a bartender who has been shaking and stirring them perhaps longer than you’ve been alive. Be sure to order one dirty—with an olive—at the wooden bar that snakes through the lounge. If you want to partake in the establishment’s most famous combos, add one of the dozen steak options to your cocktail.

Though River North is known for its nightlife, thanks to an abundance of dance clubs and trendy restaurants, it once lacked laidback establishments catering to locals. Good Measure valiantly filled that void when it opened in 2018. Housed in a former tailor shop, the bar pays homage to the historic taverns of Chicago. It’s a comfortable setting to enjoy creative cocktails by Kristina Magro and eclectic bar fare from chef Matt Troost, yielding power-packed pairings such as Japanese whisky highballs and Nashville hot fried duck livers.

Step back in time when you enter this elegant cocktail bar, tucked in the basement of The Hoxton Hotel. In addition to plenty of glitz and glam, the lounge is decked with a library nook and a baby grand piano; Lazy Bird hosts live music sessions—featuring jazz and soul—on Thursday, Friday, and Saturday nights. Its illustrated cocktail menu is stacked with all the classics, from the popular boulevardier to lesser-known creations such as the hanky panky, which mixes equal amounts of gin and sweet vermouth, finished with a splash of Italian amaro.

Modern Latinx flair meets a classic Chicago tavern at Osito’s Tap. Cocktails here celebrate agave spirits, with offerings such as La Dama, with mezcal and chile syrup. Food also takes cues from Little Village’s sizable Mexican immigrant community; grab a plate of mole rosa with chicken thighs or vegan tacos. The dishes and drinks are best enjoyed at the beautiful bar, accented by an antique mirror and ornately carved wood.

Everything about Tricycle is cute, from the pop art that lines its walls to a puppy-friendly section of the menu. But rest assured, there are plenty of human food and drink choices at this lovable, low-key bar. Whether you’re craving al fresco wings and beer—Tricycle boasts a hefty domestic brew selection—wood-grilled pizzas, or a classic cocktail, this is a neighborhood joint that has it all.