
Photo: Jay Carriker (User:JCarriker), CC BY-SA 2.5 via Wikimedia Commons
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).
The Reliance Building is a skyscraper at 1 West Washington Street in the Loop community area of Chicago, Illinois. The first floor and basement were designed by John Root of the Burnham and Root architectural firm in 1890, while the rest of the building was completed by Charles B. Atwood in 1895. It is the first skyscraper to have large plate glass windows covering the majority of its surface area—a design feature that became dominant in the 20th century. The building fell into disrepair starting in the 1940s, and was restored in the late 1990s. Since 1999, the building has housed the 122-room Staypineapple, An Iconic Hotel, The Loop and Atwood Cafe.
© OpenStreetMap contributors
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.
Adler & Sullivan, 1882
Louis Sullivan was only a draftsman at the time this was built, but there are some interesting designs nestled into expressive façade and the classic, powerful masonry walls.
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.
Oriental Theater
The Oriental Theater was once Chicago's most ornate movie palace, but this is now another Broadway in Chicago theater outlet.
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.
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.