Secret Worlds Await

A Guide to Chicago’s Best Speakeasies

By Celine Ipek

They’re concealed beneath winding staircases and tucked behind curio-filled bookshelves. They’re the spots you wander into around midnight—the spots that make Chicago a city of hidden wonder. If you like your alcohol served with a side of mystery, look no further than these seven speakeasies.

The Drifter

This is one of those spots every Chicagoan will send you to—and for good reason. Visit the downstairs of The Green Door Tavern to enter an intimate world of exposed brick walls, faded vintage posters, and circus paraphernalia. Once seated, choose a cocktail from a handful of illustrated tarot cards while enjoying a burlesque performance or juggling act. The buzzing atmosphere and fantastic drinks set you up for an unforgettable night on the town.

Room 13

If you book a stay at the Old Chicago Inn, you may be lucky enough to gain access to this members-only, Prohibition era-inspired bar. Room 13 offers classic recipes and ingredients that evoke the Jazz Age—bourbon with amaro, gin with maraschino liqueur, scotch with sweet vermouth. Don’t be surprised if you go for one drink and end up trying several.

The Office is The Alinea Group’s ode to classically inspired cocktails and artfully curated flavors. Located below The Aviary, this exclusive bar pairs colorfully woven rugs with eclectic works of art. Settle into an oversized armchair and try to choose among the antique spirits stocked in the wooden cabinet behind the bar. For an added element of surprise, opt for Dealer’s Choice and allow the bartender to craft a unique drink based on your preferences.

The Library at Gilt Bar

It’s hard to think of a dreamier venue than The Library. It has a warm, alluring interior, complete with velvet mid-century booths, fringed chandeliers, and gold-embossed books. Serving an opulent menu of American classics and cocktails from past eras, The Library invites you to indulge in house specialties like the Hemingway Daiquiri (Flor de Daña, maraschino, grapefruit, lime) and the Pegu Club (Hendrick’s gin, Cointreau, lime, bitters).

Watershed

Dedicated to serving a myriad of artisanal spirits and regional beers, Watershed offers the perfect environment for a more relaxed night out. To find it, enter through the main entrance of Pops for Champagne and head down to the basement. This cozy nook features stone walls and highbacked booths. Its cocktail menu includes the Brews Brothers (bourbon, coffee, chocolate, amaro) and the Clear Smoke (mezcal, Campari, orange, dry vermouth).

The Violet Hour

This is possibly one of the best cocktail dens for date night. Pass through a discreet entryway to discover sparkling chandeliers, milky blue curtains, and clusters of candlelit tables. Seasonally-inspired libations and sumptuous bar bites make up its ever-changing menu. And whatever you do, don’t forget to follow the house rules: no cell phone use in the lounge, no cosmopolitans, no guests that you wouldn’t bring to your mother’s house for Sunday dinner.

Brando’s Speakeasy

There’s no sign at the entrance but to find Brando’s Speakeasy, keep an eye out for a window adorned with a brightly lit martini glass. Located in the historic South Loop, this bar offers a slice of old-timey nostalgia. The space is awash in a soft crimson glow, styled with leather banquettes—not to mention a karaoke lounge. Is any night truly complete without a round of lighthearted singing?