In Chicago, lofty steel factories and hideaway speakeasies from the Prohibition era have been transformed into unique places to spend a few nights. These boutique hotels are also a part of local life, hosting some of the best bars and restaurants in town.
The Freehand Chicago is situated in River North | Courtesy of Freehand Chicago / Hotels.com
Housed in a 1920s building, Freehand combines Art Deco design with mood-lit ambience on a popular street in the River North neighborhood. Grab a latte at the in-house café or a photo-worthy cocktail at Broken Shaker, which has ranked highly on the Top 150 Bars in America and Best American Hotel Bar. With options at every price point – from quad rooms with bunk beds to a rockstar penthouse suite – you’ll find something to suit at this cool city den.
Casual, Great Location, Stylish, Design, City, LGBTQ-Welcoming, Cosy
The Robey is at the heart of Wicker Park | Courtesy of The Robey / Hotels.com
Wicker Park is full of vintage shops, small cafés and breezy patios, and The Robey sits on the neighborhood’s most coveted intersection. Built in 1929, the hotel’s reconstruction was spearheaded by a Belgian design duo with Grupo Habita Hospitality. Make sure to venture up to the Cabana Club on the rooftop at sunset for sparkling views of the skyline. Modern class meets cordial high-style at the only hotel in this part of the city.
If you only have one day to see the city, a stay at this hotel across from Millennium Park will check a lot of boxes. An atrium rooftop offers spectacular views of Michigan Avenue, the lake, the Bean and beyond. The 1893 Venetian Gothic landmark used to be an athletic club where five-time Olympic gold medalist Johnny Weissmuller swam laps. See if you can find the hidden eight-seat micro-bar that was a speakeasy during Prohibition. Elsewhere, ping-pong and signature cocktails in the game room are thoroughly entertaining.
Experience old-world charm on Chicago’s Gold Coast. Tucked among residential buildings and bordered by Lake Michigan, the Talbott features elegant, dog-friendly rooms with a vintage vibe. Stroll along the lakefront trail or browse high-end shops on Michigan Ave before dinner at a distinguished Rush Street steakhouse.
Hotel guests at this members-only creative club have access to exclusive bars, restaurants and a rooftop pool, all coveted by the average Chicagoan. The six-story building in the West Loop has 40 rooms in an industrial space commissioned by an art collector in 1907. Its features include Neoclassical tiles at the front entrance and a gym with genuine-leather boxing equipment.
Rent a bike and cruise to the zoo or Lincoln Park from this neighborhood spot. Midwestern charm and spirited creativity are palpable in the colorful design and welcoming atmosphere. A portrait of Abraham Lincoln is painted on one side of the 12-story building, and the J Parker rooftop bar is a buzzy hangout all year round. Head up there and enjoy a malört cocktail – a rite of passage for any Chicago visitor.
Built for the modern traveler, FOUND offers easy rooms in a stylish setting. Amenities such as prime parking, a stacked communal kitchen and well-designed shared rooms speak to road-trippers and adventurers. The more luxe-minded will enjoy a private room, dining at the Mason restaurant and the karaoke bar where you can sing your heart out before heading out into the cosmopolitan River North neighborhood.