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Photo: John Picken, CC BY 2.0 via Wikimedia Commons
850 ft. Located at the exact center of CTA's Loop transit system, this building is distinctive for its vertical curve. It has been renamed for each of the successive banks that have bought out its previous tenants — for example, it was the BankOne Tower until 2005. The plaza outside is more interesting than the interior — it is home to an enormous mosaic by renowned Russian painter Marc Chagall.
Chase Tower is a 60-story skyscraper in The Loop community area of Chicago, Illinois, United States.
© OpenStreetMap contributors
Shubert Theater
Another Broadway in Chicago theater. Founded in 1906 to attract a classier vaudeville crowd, it saw performances from Harry Houdini, and was run by New York theater impresario Sam Shubert for more than forty-five years. In modern times, Monty Python's Spamalot and High School Musical have played here.
Holabird & Roche, 1894
It's partially obscured by renovations, but this first-wave skyscraper still makes an immediate contrast with the modern Federal Center across the street. The lobby is decorated with Tiffany mosaics and bronze carvings of Pere Marquette, an early French explorer. There is plenty of first-floor retail to allow trips inside.
Root/Atwood, 1890/1895
A then-unprecedented amount of glass was used in this early skyscraper, bewildering a public still used to masonry walls. Note the difference between the first two floors and the ones above: hold-outs among the previous building's tenants forced developers to build the foundation and the first two floors under the top three floors from the old building, and then knock off the top three when their leases had expired. It was restored when it became the Hotel Burnham (see below) in 1999, and can be explored with a stop at the Atwood Cafe (also below).
648 ft. The 1965 Daley Center is Chicago's principal civic center and boasts a gigantic Picasso statue on the adjacent plaza. A true Chicago landmark, the Daley Center was featured in The Blues Brothers, who drive across Daley Plaza and crash through the glass walls of the building. The Mies-esque design was intended to age visibly: the color has faded in a rust-like direction from exposure to the elements.
Van Osdel, 1877
Designed by John Mills van Osdel, the city's first accredited architect after the Chicago Fire, this four-story building is one of the oldest in the Loop. The two bottom floors were remodeled by Louis Sullivan in 1896, adding some interesting cast-iron designs for its use as a department store.
Burnham & Root, 1888
The Rookery is gorgeous to the point of absurdity, with delight to be found in details in the rustic lower walls and the triumphant upper walls. (Note the helpful street names carved in the corners.) Named for pigeons' habit of roosting in the then-new skyscrapers, this was the first Loop building to be granted preservation status in 1972. The lobby was remodeled in 1907 by enfant terrible Frank Lloyd Wright, adding his own touch to the interior.