Doubling down on the secrecy, Three Dots added a speakeasy-within-a-speakeasy, The Bamboo Room. Rum-centric drinks are served in elaborate-and highly sought-after-tiki mugs, along with gussied-up Polynesian faves like crab rangoon and spring rolls. It all culminates in a sprawling windowless room that feels more Disney World than Chicago, albeit decidedly more adult.
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That’s thanks as much to its masterful mixology, its immersive Pirates of the Caribbean-esque atmosphere, and its groundbreaking premise-guests follow a series of flickering tiki torches down a River North alley, then enter an unmarked door into a long hallway lined with glowing skulls. When it first opened its hidden alleyway door in 2013, at the forefront of the nationwide tiki renaissance, Three Dots and a Dash quickly cemented itself as one of the most quintessential bars in the country.
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How to book: Nine Bar does not take reservations, so arrive on the earlier side (pre-7 pm) to stake out a seat. Come hungry too, ‘cause the snackable food menu is packed with heavy-hitters like mapo hot fries, a McKatsu fried pork sandwich, and crispy cauliflower in Chinese orange sauce. This being Chinatown, look for Chinese-inspired tipples and spirits, including lots of highballs, sakes, and a masterful Mai Tai made with almond cookie orgeat. Housed in what was once a dining room for the restaurant, the alluring bar is marked only by a blink-and-you’ll-miss-it sign that bears the Chinese characters for “Nine Bar,” which gives way to a sexy den filled with lounge chairs, stools, a DJ booth, and flashes of neon. That all changed in 2022, when Nine Bar emerged as the neighborhood’s first cocktail bar, a dimly lit speakeasy nestled behind Moon Palace Express. Photo courtesy of Osito's TapĬhicago’s Chinatown has long been a haven of soup dumplings and chili chicken, but craft cocktails? Not so much. How to book: Stop by for first come, first served seating.
The bar can be accessed by entering through the red door on Chicago Avenue, just past The Martin gallery’s entrance. While billing itself a “neighborhood lesbian cocktail lounge,” all are welcome (except homophobes) to come partake in snazzy cocktails like Bad Poetry, made with coffee liqueur, mezcal, Campari, and egg white. Dorothy is located underneath Split-Rail, the lesbian-owned restaurant known for its killer fried chicken, and it harkens to ‘70s glam with a retro motif filled with disco balls, wood paneling, vintage furniture, and velvety wallpaper. Today, a new-ish bar in Ukrainian Village pays homage as a subterranean speakeasy-style oasis. In decades past, discreet queer folks identified each other with the phrase “a friend of Dorothy,” so as to find solidarity without blatantly outing themselves. For different reasons, LGBTQIA+ bars have long been forced to operate at some level of discretion, in order to protect its patrons from homophobia and raids.
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