These Windy City speakeasies are worth a little extra hunting.
Chicago, the city of baseball and hotdogs, architectural innovation and world-class gastronomy, is a beacon of American identity. Industrial legacy, characters like Al Capone, and the gritty days of prohibition direct our collective imagination to a time when the saloon, a cornerstone of social life, was driven down into the hushed dens of illegal speakeasies. Thankfully the 18th Amendment was repealed, but the tradition of underground watering holes is still strong in Cook County. Hidden doors, alley entranceways, and discrete passages mark these five hidden bars, where premium drinks and atmosphere combine in alchemic harmony.
The Violet Hour
The entrance to this award-winning Wicker Park boite is camouflaged in street art. Scan the graffitied wall on Damen between Pierce and Le Moyne for the painted-over door, then head past a stern doorman who will caution you about cellphone use here. Inside the lavender room, high-backed gothic chairs are arranged in pods before your arrival. A sophisticated seasonal menu, organized by liquor, is evangelized by passionate staff who help navigate the specialty lists of potable bitters and absinthes. Stick with a classic from the catalog of bourbons, or venture into punch bowls and cocktails with ingredients from Genepy de Alpes to Root Beer bitters.
Three Dots and a Dash
Swizzling and stick-blending are the name of the game at this underground tiki spot from the Lettuce Entertain You empire. The clever moniker is Morse code for “victory,” the World War II success signal that was later turned into a celebratory cocktail by tiki king Don the Beachcomber. This bar is darkly Polynesian with wood-paneled interiors and black-lit skulls crowding the entrance corridor. Though the address is on North Clark, turn the corner to the alleyway to find the front door. Friendly ladies in flowered skirts will bring you garnished drinks in cups that you can take home for a fee.
The Aviary’s Office
The Office is the Alinea Group’s yin-yang answer to the hyper-manicured Aviary, with its gastro-leaning drinks and 40 types of ice. Not that the drinks at the Office are any less inspired. While upstairs you’ll find slick white furnishings and a spotlighted bar space, this downstairs lounge-within-a-lounge is a cross between Hemingway’s lodge and a Harvard reading den. Brass-studded leather chairs, stacked frames, and glass liquor cabinets make a leisurely enclave for house cocktails that are curated by flavor profile and ingredients. You can order off the menu or ask the bartender to make something to your liking. Bar snacks like foie gras-stuffed Snickers bars are whimsically satisfying.
This hole-and-corner nook in the back of the Freehand Hotel brings heavy-hitter guest talent like the Dogma Group and Ben Schiller to a menu already rife with classics. Drinks like the Log Cabin Old Fashioned, made with maple syrup and bacon bitters, are exemplary of the bar’s creative take on the typical cocktail. A full page of Sherries and bar snacks like naan nachos and short rib sliders are destination-worthy embellishments. Make your way to the back of the lobby and up the stairs for this discrete watering hole.
There is a small sign at the entrance to this West Loop newcomer tucked underneath the L, but the rusty afterthought of a door makes it feel hidden anyway. At Moneygun, the leather banquettes are large and the menu is stocked with detail-driven classics. The group tapped Michelin-starred chef Jared Wentworth from Longman and Eagle for its inspired list of bar snacks, which includes Kentucky-fried quail and gin-cured olives. Its hushed opening and “just a bar” vibe make us want to keep it on the DL.