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Photo: User:JeremyA, CC BY-SA 2.5 via Wikimedia Commons
961 ft. For a time this was the tallest building in the world without an official name, although locals know exactly what to call it: The White Castle Building. It is distinctive for its "crown," which is brightly illuminated at night. If you are nearby, head into its lobby to see its enormous indoor garden and fountain.
311 South Wacker Drive is a post-modern 65-story skyscraper located in Chicago, Illinois, and completed in 1990. At 961 feet tall, it is the ninth-tallest building in Chicago and the 36th tallest in the United States. It was once the tallest reinforced concrete building in the world. 311 South Wacker was also the tallest building in the world known only by its street address, until it was surpassed in height by New York's 432 Park Avenue in 2015. 311 South Wacker occupies a prominent position in the Chicago skyline, being located on the block immediately to the south of the Willis Tower.
© OpenStreetMap contributors
Once the tallest building in the world, the Sears Tower (officially renamed the Willis Tower) now has to settle for second-highest in the Americas alone, behind New York City's One World Trade Center (and even those are after a semantic battle with Toronto and the CN Tower). The Hancock Observatory (see Near North) has a nicer view of the city, but the Sears Tower offers an incredible view of its own from "The Ledge", which lets visitors walk out in a transparent balcony suspended 1,353 feet above the street. To avoid the crowds, visit after 4PM.
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.
Currency wonks can study various denominations and practice counterfeit detections. Guided tours every day at 1PM.
1007 ft. Built by Adrian Smith in 1989, the granite-clad AT&T Corporate Center is one of the city's more distinctive skyscrapers for its massive size, spiked roof pinnacles, and a style evocative of both Gothic and Japanese architectural styles. It's not well-known, but it is the eighth tallest building in the U.S.
Sullivan/Holabird & Roche, 1898-1902
Louis Sullivan designed the northernmost (18) of the three buildings here, and the team of Holabird & Roche added the next two (24 & 30). The roots of Mies-style modernism are easily apparent in the immaculate proportions here, although Sullivan's piers overflow like water-pipes with ornament at the top, and Holabird & Roche's two make an interesting contrast with the master.
The 4th Floor Visitor Gallery is temporarily closed.