21 E Bellevue Pl, Chicago, IL 60611, USA
Thompson Chicago, housed in a contemporary high-rise in the heart of the Gold Coast luxury dining and shopping scene, was overhauled in 2013 by British designer Tara Bernerd. It offers a winning combination of modern-retro style, a home-away-from-home ambience, attentive service, and value for money. (The building previously was home to the Sutton Place Hotel.) With Thompson Hotels’ arrival, the lobby, dominated by a huge shelved library cube filled with books, curios, and retro bull’s-eye mirrors, now strikingly harmonizes industrial exposed brick and dark-wood beams with elements paying homage to Chicago architect Frank Lloyd Wright (think geometric tiles and a cantilevered staircase). Most guestrooms have astounding city and Lake Michigan views, and all are snazzily furnished with asymmetrical velvet sofas, enormous showers, and framed contemporary art by the likes of Wes Lang. It’s a style that impresses without being intimidating.
2657 N Kedzie Ave, Chicago, IL 60647, USA
In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”
1331 N Wicker Park Ave, Chicago, IL 60622, USA
On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.
113 N Green St, Chicago, IL 60607, USA
Unlike other locations of this hip members-only club, Chicago’s Soho house offers some access to the public, winning over both guests and locals with its comfortable first floor and mezzanine areas, Cowshed spa, and eateries like Chicken Shop, which specializes in free-range rotisserie chicken. Soho House’s members are generally creative, open-minded types who prefer comfort over formality. Anyone, however, can book a hotel room—and with a room key comes all the perks afforded to members, like access to all restaurants, the gym (which features a professional boxing ring), a movie screening theater, and the swanky rooftop pool and bar. Rooms come in sizes tiny, small, medium, medium plus, and big, and are peppered with delights like china tea sets and crystal decanters.
203 N Wabash Ave, Chicago, IL 60601, USA
Virgin opened its first U.S. hotel in a 26-story, 1920s art deco tower. Originally a Chicago bank, the building’s high-ceilinged, second-floor hall has been transformed into the Commons Club, a socializing spot divided into a lounge, dining room, and oval-shaped zinc bar with red leather seating and power outlets for tech-addicted travelers. Apartment-like rooms are smartly divided by sliding doors into two sections: a sleeping lounge, and a large dressing and bath area.
455 N Park Dr, Chicago, IL 60611, USA
This purpose-built luxury high-rise hotel has 400 rooms in all, with natural light spilling through floor-to-ceiling windows onto modern, clean-lined furnishings done in ivory and gray tones. Higher floors offer spectacular views of Lake Michigan and Navy Pier. Service here gets high marks for the nothing-is-impossible attitude of the staff, and from early summer to late fall the Streeterville Social, the third-floor roof top outdoor terrace, offers craft cocktails and relaxed dining… and views of the city skyline.