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Photo: David K. Staub, CC BY-SA 2.5 via Wikimedia Commons
Named appropriately for a mountain in New Hampshire, the Monadnock was the last tall building to be supported by its own walls (not a metal frame, although the 1893 addition by Holabird & Roche does use one). It's a masterpiece of simplicity and power in form. The block-long hallway that serves as a lobby has incredible ambiance: it's always kept at a level of brightness that suggests gas lamps, and the small stores on the first floor (a coffee shop, a shoe-shine, a restaurant) are all turn-of-the-century tile-and-polish.
The Monadnock Building is a 16-story skyscraper located at 53 West Jackson Boulevard in the south Loop area of Chicago, Illinois, United States. The north half of the building was designed by the firm of Burnham & Root and built starting in 1891. At 215 feet, it is the tallest load-bearing brick or masonry building ever constructed. It also employed the first portal system of wind bracing in the United States. Its ornamented staircases represent the first structural use of aluminum in building construction. The later south half, constructed in 1893, was designed by Holabird & Roche and is similar in color and profile to the original, but the design is more traditionally ornate. When completed, it was the largest office building in the world. The success of the building was the catalyst for an important new business center at the southern end of the Loop.
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van der Rohe, 1964/1975
This plaza includes Mies' Dirksen Federal Building and Kluczynski Federal Building (built eleven years apart), with a low-rise post office enveloped in their sleek black lines. But the buildings are not quite as famous as the gigantic red constructivist flamingo statue by Alexander Calder in the plaza in front of the post office. An adventurous raccoon may have set a raccoon world climbing record by reaching the scaffolding on the 36th floor in 2006.
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.
287 ft. While not very tall, this 1975 brutalist structure is one of the most distinctive and curious in the Chicago skyline. As its name suggests, it is a vertical prison skyscraper and its sharp triangular shape is designed to minimize the amount of time that it takes to patrol its corridors. Its prisoners have some of the prison world's best views as their exercise yard is on top of the roof, although the narrow slits serving as windows do not allow such nice views from the cells. The prison houses male and female convicts of all security levels, waiting for transport to the courthouse nearby.
Currency wonks can study various denominations and practice counterfeit detections. Guided tours every day at 1PM.
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.
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.