A Former Chicago Mafia Haunt Reborn as a Hotel

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By Huckberry / Published by Huckberry
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In the art-filled River North neighborhood, this former Prohibition-era hotel is building a sense of community

Walking through the doors of Freehand Chicago feels like stepping into a 1920s speakeasy, but with all the makings of a modern-day millennial hang out. It’s no surprise the location once played host to Chicago’s Mafia elite in the Prohibition era, when illicit liquor trade fueled secret soirées lasting well through the early morning hours. Thriving on the original foundation as a meeting place for locals, conversation is plentiful at Freehand Chicago, and guests don't feel the need to stick only to their rooms, instead mingling throughout the hotel. 

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To the right is the hotel’s reception, with a mosaic-tiled background – it's like they set up the Instagram capture just for you. Potted succulents line the windowsill, just above an over-sized, inviting couch, which offers travelers a respite from life on the road. If first impressions tell a story of any hotel, then Freehand Chicago’s story is one of friendly comfort in a thoughtful setting, deeply exuding the flavor and culture of Chicago. 

 To the left of reception is Café Integral, a coffee bar concept ideated and developed by Nicaraguan coffee entrepreneur César Vega. The menu is comprised of coffee classics and small bites by day, and artisanal coffee cocktails by night, with special recipes nodding to Vega’s Latin American roots and Miami upbringing.

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A straight walk past reception and Café Integral leads to the elevators, which also serves as the entrance to Freehand Chicago’s den. It’s as cozy and dimly lit as you could ever hope, as well as thoughtfully designed with the aesthetic of Chicago and Lake Michigan in mind. Sofas and leather chairs line the perimeter to create pockets of communal lounge spaces, with wood-paneled walls, fireplaces, books, and games making it feel more like a living room than a hotel. A Wurlitzer electric keyboard frames the nook where Freehand hosts musicians, creating an ambiance as conducive to creativity as a celebrated neighborhood coffee shop. 

Up a few steps, behind the den and past the DJ booth, is the Broken Shaker, a mixology bar serving drinks like the Chicago Dog Margarita and the Chi City Mule in glasses as beautiful as the cocktails are delicious. The bar walls are covered with pine tree wallpaper, and the relaxed and refined aesthetic is prevalent in both ambiance and flavor, with local Midwestern ingredients purposing the menu items. Rooms aside, the Freehand Chicago is the place to be in the city’s burgeoning River North neighborhood.

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This hotel and hostel hybrid is the second installment of Sydell Group’s Freehand Hotel collection, and is equipped with both private and shared rooms for a total of 336 beds on the property. Eighty rooms are shared format, offering four bunk beds and lockers per room; each bed has a private charging station, lamp, and reading shelf. 

Design firm Roman and Williams led creative direction of the interiors, manifesting an immediate sense of Chicago in the rooms and communal living spaces. Woven fabric instillations commissioned by local artisans adorn each private room, squarely centered above the beds to create a striking sense of place, capturing Midwestern pastimes like quilting circles and sewing bees in a fresh, modern, design-forward way.

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But before Freehand Chicago became what it is today, the property was originally dubbed the Devonshire Hotel, which opened in 1927 and quickly became a popular Mafia hangout of the time. The in-house coffee shop served as a meeting point for mobsters, who famously ran their operation up and down Ohio Street. After the era of Chicago’s Mafia and before River North transformed into the city’s cultural hub, the property was known as the Tokyo Hotel, which was better known for its criminal activity rather than hospitality. But with the Sydell Group’s purchase of the hotel in 2013 and the opening of Freehand Chicago in June of 2015, the hotel now stands as a pillar in River North’s vibrant cultural scene, having the highest concentration of art galleries, boutiques, and restaurants of any Chicago neighborhood.

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True to Freehand’s social spirit, I met Café Integral Founder César Vega by happenstance during my visit, just after ordering a cortadito from his coffee bar. The young entrepreneur is approachable and unassuming, intelligent and insightful, all while pointing me in the direction of his favorite ramen restaurant in the area. Vega first learned of Freehand through the group’s initial location, Freehand Miami. The hotel changed his perception of his hometown, offering a unique and atypical alternative to the popular club scene. When the idea of collaborating on the Freehand Chicago location came to fruition, Vega saw it as a natural fit given the synergies of his company and Freehand. And in his own right, Vega is a reflection of the people you meet while staying at Freehand Chicago – all are open to conversation, friendly, and looking for more depth out of a hotel stay. 

Freehand Chicago capitalizes on this concept by facilitating connection and community, offering the ideal space for exchange between travelers and creating those lasting moments we all relish. Chicago is synonymous with great food and Lake Michigan, with tourists flocking to Millennium Park to take pictures under the city’s iconic Cloud Gate sculpture. But Freehand Chicago provides a more authentic value, pointing guests towards local concerts and offering on-property dreamcatcher workshops, den music sessions with local artists, and watercolor painting classes. Freehand Chicago is refined yet accessible, both modern and authentic, and brings a new sense of place and community to the Chicago hotel experience. 


[H] Originally published at Huckberry.com

Words by Michaela Trimble