The Bedford serves classic cocktails near an original bank vault.

The Bedford
Wicker Park’s supper-club-inspired den in the historic Home Bank & Trust boasts a thoughtfully crafted cocktail menu; admire the original vault room’s floor-to-ceiling lockboxes while sipping on the signature Cucumber Cooler, or try the Pimms Cup & Tonic with lemongrass and basil tonic. 1612 W. Division St., 773-235-8800

The intimate lounge beneath Gilt Bar is reminiscent of a bygone speakeasy, with tufted leather banquettes, glowing candlelight, and a libation list that ranges from chartreuse cocktails to tiki drinks. The formerly cash-only club now accepts credit, making it even easier to get a drink down low. 230 W. Kinzie St., 312-464-9544

Double A
Mixologists Tad Carducci and Paul Tanguay create drinks like the Spaghetti Western with London Dry Gin, Campari, Cointreau, maraschino, and blood orange at this exclusive 65-seat lounge below Latin hot spot Mercadito. 108 W. Kinzie St., 312-329-9555

DiSotto Enoteca
Scott Harris’s Francesca’s tradition thrives underneath Streeterville; the cavernous hideaway’s moniker loosely translates to “underground wine bar” and delivers a well-curated selection of French and Italian whites and reds. 200 E. Chestnut St., 312-482-8727

The Office
A table at Next is easy to get compared to the 20 sought-after seats at this invitation- or reservation-only speakeasy in the basement of adjacent watering hole Aviary. Headed by mixologist Jason Cevallos, the separate menu features $20 cocktail combinations like Cognac, tonka, quassia, smoked black pepper, and vanilla bean. 955 W. Fulton Market, 312-226-0868

SUB 51
Friday and Saturday nights see Chicago’s trendsetters spilling into the private space below HUB 51 for exclusive bottle service. DJ Spider and Chris Kennedy have been known to take the helm of the club’s state-of-the-art Funktion-One sound system. 51 W. Hubbard St., 312-828-0051

This Old Town hideaway offers a sweet spot for celebrating with house specialties like the Whiskey with Sour and martinis such as the Pop Star martini with Ketel One Citroen, watermelon liqueur, and Champagne complete with a Pop Rocks trim. 1446 N. Wells St., 312-787-6103

Timothy O’Tooles Pub
With more than 60 HD flat-screen televisions and 48 beers on tap, this Streeterville sports bar is the next best thing to watching the Bears at Soldier Field. Cocktails like the Honey Hot Toddy and Captain’s Spiced Cider will make braving the elements more bearable. 622 N. Fairbanks Ct., 312-642-0700

The Underground
This River North destination nixes the velvet rope attitude so everyone can indulge in cocktails like The Hummer and The Bombay General. The hidden hot spot also showcases up-and-coming local musicians for its First Listen program on Thursday nights. 56 W. Illinois St., 312-644-7600

The 1,500-square-foot space tucked below Tree Studios features exposed limestone foundations and focuses on regional products within the Great Lakes watershed. The Dwight Yoakam–inspired cocktail Smoke Along the Track offers a spin on the old-fashioned with Lion’s Pride Whiskey from Koval Distillery. 601 N. State St., 312-266-4932

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