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.

Tucked in the back of the Freehand Hotel, Broken Shaker channels a Miami escape. But don’t let its small size fool you—this tropical bar packs a serious punch. As do the drinks, which evoke that beach vacation you’ve been lusting after. Try a Dance Yrself Green with gin, spinach, and lemon, or turn up the heat with the tequila-based La Mera Verdita, which includes jalapeño, mint, and Thai bitters. A concise food menu offers some thirst-inducing snacks plus handhelds.

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.

West Town’s Dorothy bills itself as a neighborhood lesbian cocktail lounge but its aim is to create an inclusive space for people of all marginalized genders. It’s set below American comfort food favorite Split-Rail (and owned by the same team), channeling the 1970s with plush velvet couches, a vintage wood bar, cozy nooks, and disco balls galore. A concise cocktail menu leans into reimagined classics, such as the Dorothy Martini made with Irish gin, aperitif wine, and bitters.

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.

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.

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.

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.

Between them, Le Midi owners Craig Perman and Seth Wilson have 45 years of experience in the wine and hospitality industry at some of the city’s top restaurants including Alinea, Blackbird, and RPM Steak. In the process, they’ve established close relationships with wine producers throughout Europe, reflected in the rotating selection of the 250 labels on offer. Since opening in 2022, Le Midi swiftly established itself as part-wine shop, part-wine bar, and all-around laidback spot to explore.

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.