Only in Chicago can a hotelier reasonably hope to set up shop in a masterwork like the 1929 Art Deco Carbide & Carbon Building, with its stately dark stone and immaculate gold trim. It’s a perfect fit for Pendry, the urban luxury-boutique cousin to the Montage resorts; Pendry Chicago combines contemporary boutique-hotel good looks with upscale comforts and impressive views of the distinctive Loop cityscape.

A fixture in both central London and downtown Manhattan, the Soho House members’ clubs have been expanding, both to far-flung global locations and to major cities in the United States. And it’s in a picturesque 1908 industrial building in the neighborhood of Fulton Market that you’ll find Soho House Chicago, an establishment that is, if you’ll forgive what sounds like overstatement, much more than simply a hotel.

This Venetian Gothic landmark, previously a private club for the city’s (male) movers and shakers, dates back to the final decade of the 19th century. But now, after a renovation by architects Hartshorne Plunkard and an interior redesign by hospitality wizards Roman and Williams, the Chicago Athletic Association is a thoroughly up-to-date boutique hotel, in that retro-modern, luxury-boutique sort of way.

It makes sense that a hotel in Wrigleyville would pay homage to Zachary Taylor Davis, the architect behind the Chicago Cubs’ Wrigley Field. Sitting just across the street from the ballpark, this boutique hotel has paid particular attention to design, just like its namesake, mixing classic and mid-century styles. For baseball fans, rooms also come with Wrigley Field views.

When one of your favorite hotel brands moves into one of your favorite underutilized buildings, it’s a win-win. The Robey Chicago, from Grupo Habita, occupies North Tower, a 1929 Art Deco skyscraper in Wicker Park. The Mexican mini-chain tapped a Belgian design team, Nicolas Schuybroek Architects and Marc Merckx Interiors, to overhaul the place. The look is cool and industrial with a vintage twist.

One of many hotels to have learned the lessons of the apartment-sharing boom, Guesthouse Hotel offers one-, two-, and three-bedroom suites, each one fit for as long a stay as you’d like. They’ve got high ceilings, full kitchens, and private balconies complete with gas grills overlooking the quiet neighbors at Andersonville’s St. Boniface Cemetery. A roof deck, Club Room, and Library allow for some low-key socializing.

The Viceroy hotels exist at the intersection of luxury-hotel extravagance and boutique-hotel tastefulness, and the Viceroy Chicago is no different. The building, a gently undulating glass tower, is pure luxe modernity, but the lower floors blend effortlessly into Chicago’s Gold Coast, thanks to the meticulously preserved façade of the 1920s-vintage Cedar Hotel, which was reassembled brick by brick.

Nobu Hotel Chicago stands over a stretch of Randolph Street known as Restaurant Row, but it doesn’t simply coasts on its kitchen’s reputation. The rooms and suites are Japanese-influenced, equal parts Zen and ultra-modern post-industrial — check out the cedar tubs in the suites — and they’re as luxurious as they are stylish, with plush beds custom-designed for Nobu and upscale conveniences.

For Sofitel Magnificent Mile, architect Jean-Paul Viguier was allowed to start from scratch, and the result is striking — a dramatic bright white wedge-shaped building that looks like a giant ice breaking ship cutting its way across Chicago. The inverted wedge shape has a delightful effect on the interiors as well — some guest rooms protrude out over the sidewalk, allowing a unique view straight down onto the street.

True to its name, the Publishing House Bed and Breakfast was once the Free Methodist Publishing House (and a casket factory, and a holograph museum). A Chicago institution, in other words, inside and out it’s a love letter to well-crafted design and material details like the double-sided fireplace in the public great room. Each of the 11 en-suite rooms is dedicated to a local author.