Eighteen rooms across the city: Streeterville's five-stars and lake views, Loop landmarks like the Athletic Association, the Hoxton and Soho House in the West Loop, a Wicker Park tower and a Hyde Park hotel that finally gives the South Side its own good keys.
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Service that anticipates you before you ask. The Z Bar terrace looks out over Michigan Avenue, the fifth-floor pool is glass-walled, and the rooms are the quietest on the Mag Mile.
Pip’s Tip Glass-walled pool and the Z Bar terrace over Michigan Avenue. Afternoon tea is a proper service here.
Seventh-floor NoMI Garden puts you eye to eye with the old Water Tower. Rooms are calm and low-lit with deep tubs, and a serious art program runs through the halls.
Pip’s Tip NoMI Garden on the seventh floor puts you level with the old Water Tower. Ask for a lake-facing room.
High floors above the shops at 900 North Michigan, so the lake fills the window. Adorn handles dinner, the Roman-style pool handles the morning, and the staff remember your name.
Pip’s Tip High floors above the shops at 900 North Michigan, so the lake fills the window. Indoor pool.
A cobblestone courtyard off Walton Street, then suites with gas fireplaces and separate living rooms. The most residential-feeling luxury address in the city, and easily the quietest.
The 1920s Cedar Hotel facade with a glass tower rising behind it. Devereaux on the roof has the pool and the skyline; rooms run brass, walnut and deep blue.
Tucked on Bellevue Place a block off Rush Street, so you get the nightlife without the noise. Salone Nico does the Italian, and the corner rooms look straight down State.
Mies van der Rohe designed the building and the hotel keeps those mid-century bones, then adds the largest bathrooms downtown. Chuan Spa and the Travelle bar both earn repeat visits.
Small smart rooms, big social floors. The lobby bar runs late and the rooftop puts you above River North, which is exactly where you want to be around midnight.
The Carbide and Carbon Building in black granite and gold leaf, restored properly. Chateau Carbide on the roof looks straight down Michigan Avenue, and Venteux handles the brasserie side.
An 1893 gentlemen's club turned hotel with the wood paneling and billiards left intact. Cindy's on the roof faces Millennium Park; the Game Room downstairs is where the night actually happens.
Jeanne Gang's rippling tower on the river, with butler service and floor-to-ceiling glass over the lake and the locks. Tre Dita downstairs is the Tuscan steak room worth the reservation.
Cedar, stone and low light, done with real restraint. The Nobu dining room and rooftop bar pull the whole neighborhood in, and the rooms stay serene several floors above it.
A warehouse conversion on Green Street with a lobby you can genuinely spend a day in. Cabana Club on the roof has the pool, and Fulton Market's kitchens start at the door.
Concrete, timber and daylight in the old Ace Hotel building, now running independent. Loft rooms with turntables, a leafy courtyard, and Fulton Market restaurants two minutes in any direction.
A 1907 belt factory with bedrooms you can book without a membership. Rooftop pool, a screening room, Cecconi's on the ground floor, and the best-worn leather in Chicago.
The 1929 Coyote Building at Wicker Park's six corners. Narrow Deco rooms with tall windows, and a thirteenth-floor bar that watches the whole intersection do its thing.
Across Clark Street from Wrigley Field, and some rooms look right into it. Handsome brick and brass throughout, good drinking downstairs, and Gallagher Way out the front door.
The only real design hotel on the South Side, built around Hyde Park's own story. Commissioned neighborhood art throughout, Mesler for dinner, and the lakefront and the Museum of Science and Industry close by.
The 1893 clubhouse reopened, Cherry Circle Room downstairs, Cindy's rooftop over the park.
Group rates when the family travels. Members hear first.
Stays are one chapter of Pip's Lifestyle, find the lounges, rooftops, brunch spots and the Domino Club below.
