Chicago’s 8 favorite bars

The team behind West Loop fine-dining sensation Oriole runs this intimate 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 hard-to-find sake and rare green teas—and creative small plates were instant hits after Kumiko opened its doors in 2018, earning it a mention as one of Time’s Greatest Places in 2019. Even the bar’s spirit-free section goes above and beyond, with ingredients such as shiso-pickled ume and purple sweet potato vinegar. The food menu has expanded since opening, and now includes a sought-after wagyu katsu sando.

At Centennial, the beers-on-tap limit does not exist, reflected by a prolific selection that includes 56 types, from malty maibocks to fruity sours. Unusual bottled and canned beers find a welcome home here, too, such as a peanut butter porter from an independent craft brewery in Illinois. Centennial’s wine and spirits selection takes a similar road-less-traveled approach, focusing on craft producers and distillers. Enjoy it all in a 19th-century building with plenty of rustic charm—case in point: the salvaged Brunswick bar on the second floor. All the food here is listed with a suggested beer pairing (including an extensive selection of shareable items), with winning combos such as house-smoked beer-braised ribs and a Pilsner.

Named the best bar in Chicago by the Jean Banchet Awards in 2022, The Alderman might be the hottest one in town—and not just because there are only 16 seats inside its speakeasy-esque confines. The dark and moody bar is an ideal place to sip on something strong, and 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 F.A.F.O., a floral cocktail that blends Spanish gin with Chicago’s love-it-or-hate-it spirit Malört (a wormwood-based digestif).

What started out as a humble neighborhood pizzeria in 1962 has since become a charming wine bar, earning Wine Spectator’s Award of Excellence in the process. Angelo’s is nothing if not nimble. It’s loved for a global wine list focused on small-batch vineyards, with about 25 by-the-glass and half-glass offerings. Vermouth is made in house here, and there’s even a barrel-aged beer program. And, yes, pizza is still a focus at Angelo’s, with both Chicago and old-world styles available with toppings such as fig, prosciutto, and roasted garlic cream. It is, after all, the neighborly thing to do.

Gibsons still reigns as a favorite for both tourists and locals in a city filled with solid steakhouses. Its lounge is equally iconic, with its tin ceiling and shiny curved wooden bar that snakes through the sophisticated space. Come here for a vintage cocktail experience—the ice-cold martinis are made by a bartender who has been shaking and stirring them perhaps longer than you’ve been alive. And be sure to order one dirty—with an olive or two. If a celebration is part of the evening’s activities, Gibsons is happy to oblige with six sparkling wines by the glass available. Should you want to get what the restaurant is most famous for, add one of the dozen steak options to your drink order.

Step back in time when you enter this elegant cocktail bar in the basement of The Hoxton Hotel. In addition to glitz and glam, the intimate 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 lovely illustrated cocktail menu, which includes a brief story for each drink, 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 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. Osito’s leans deeply into the culture and roots of its surrounding community, which comes naturally from its parent company, Moreno’s Liquors, a family-owned Pilsen mainstay since 1977. As with any thoughtful bar these days, Osito’s offers some intriguing spirit-free drinks, including the Chicha Morada, a Peruvian drink made with purple maize, pineapple, and cinnamon. 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.

With 90 craft beers on draft—including about 30 from local breweries—Old Town Pour House caters to a suds-seeking crowd. For the indecisive, there are six-ounce pours or beer flights. Cocktails lean towards remixed classics, such as the mezcal margarita made with lychee syrup and orange flower water. Large flatscreens are tuned to the latest game above the long line of colorful draft handles, and all are easily visible from just about any seat in Old Town’s open, lofty space. Expect a menu that isn’t afraid to get creative with classic pub fare, featuring fried pickles, Korean sliders, and kung pao cauliflower.