Chicago may be a large and important city, but it has long lacked a luxurious hideaway hotel. All the properties we currently recommend have more than 200 rooms. It has seemed ridiculous that such a major metropolis couldn’t support at least one smaller hotel of potential interest to Hideaway Report members. The 40-room Soho House looked promising when it opened a few years ago, but amateurish service prevented us from recommending it. Since then, a number of other boutique properties with aspirations have opened in the city. Hopes high, we booked our tickets to return.

Most visitors quite understandably stay in River North near the shopping of Michigan Avenue (the “Magnificent Mile”) or in the adjacent Loop, which is the central business district immediately to the south. I used to prefer the former, but now the revitalized Loop is more appealing, with its easier access to Millennium Park, the Art Institute of Chicago and the West Loop restaurant district. It was in the Loop that the world’s first true skyscraper was built, and the first skyscraper to have a façade composed mainly of glass still stands there today: The elegant Reliance Building should be a stop on the itinerary of any architecture buff.

Chicago’s pride in its historic architecture is obvious, both downtown and in well-preserved residential neighborhoods surrounding the center. An architectural boat tour along the Chicago River is almost mandatory for first-time visitors to the city. I’ve done three or four such cruises now, and every time, I learn something new. On a previous visit to the city, I also explored its Frank Lloyd Wright architectural heritage, including his fascinating home and studio in suburban Oak Park, the nearby Unity Temple and the graceful Prairie-style Robie House in the Hyde Park neighborhood on the city’s South Side.