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One of the earliest remaining skyscrapers, this 1888 Chicago landmark combines traditional wall-bearing and newer steel frame construction. The latter made it possible for its architects, Burnham and Root, to design an open interior, with office spaces set around a central light well.

Built by Adler and Sullivan in 1889, the ornate Auditorium also originally contained a hotel and office building and had one of the first public air-conditioning systems. The revamped 4,000-seat theater boasts near-perfect acoustics.

Constructed in two stages, this Loop edifice represents the evolution of skyscraper architecture. The northern half was built in 1891 using solely wall- bearing construction, while the southern half was built two years later and incorporated the then emerging steel-frame technology that is still used today.

The steel skeleton on this 1895-built skyscraper allowed it to be wrapped in glass. It offers an excellent example of the Chicago window, which is characterized by a bay window placed between two narrow, double-hung windows – a signature feature of the Chicago school of architecture. Occupied by the Hotel Burnham the interior sports replicas of original features.

You might think these two highrise apartment buildings (1949–51) look like many others along this tony strip. Actually, the others look like these. German architect Mies van der Rohe perfected the “less is more” approach which so many other architects went on to copy.

With its twin cylindrical structures (1964–7) on the Chicago River, marina City is a “city within a city”, containing offices, residences, a theater, a grocery store, and more. The apartments start on the 21st floor, affording spectacular views, but their slice-of-pie shape creates some interior decorating challenges.

This soaring tower, built in 1974 as the headquarters of retailer Sears Roebuck and Co. (who have since moved out), can be seen from almost anywhere in the city. Its Skydeck affords sensational views (see Sears Tower & its Views).

The graceful curve of this triangular, tinted-glass office building (1983) hugs the Chicago River. The water, together with the changing light and clouds create dynamic reflections: the green and silver lobby continues the shimmering show.

From inside the circular atrium of this magnificent 17-story building (1985), a quick glance up is almost dizzying. Take the elevator to the top for an impressive view of the stunning marble rosette on the concourse level.

Rising 40 stories in waves of glass and steel is this striking 1996-rebuilt commuter train station (aka the Northwestern Station). Its streamlined façade mimics a vintage luxury train.