Two Prudential Plaza

Two Prudential Plaza is a skyscraper that was built in Chicago in 1990. At 303 m (995 ft) tall, it is the fifth-tallest building in Chicago and the eleventh tallest in the United States. The building was designed by the firm Loebl, Schlossman & Hackl, with Stephen T. Wright as the principal in charge of design. It has also been honored with 8 awards, including winning the Best Structure Award from the Structural Engineers Association of Illinois in 1995.

John Hancock Center

The John Hancock Center at 875 N. Michigan Ave. in Chicago, Illinois, is a 100-story, 344 m (1,127 ft) tall skyscraper designed by structural engineer Fazlur Khan of Skidmore, Owings and Merrill. When completed in 1969, it was the tallest building in the world outside New York City. It is the third-tallest skyscraper in Chicago and the fourth-tallest in the United States, after the Sears Tower, the Empire State Building and the Aon Center. When measured to the top of its antenna masts, it stands at 457 m (1,500 ft). The building is home to offices and restaurants, as well as about 700 condominiums and contains the highest residences in the world. This skyscraper was named for its builder the John Hancock Insurance company.

The 95th floor has long been home to a restaurant, the latest tenant being "The Signature Room on the 95th Floor." While patrons dine, they can look out at Chicago and Lake Michigan. The Hancock Center's observation facilities compete with the Sears Tower's Skydeck across town. The Hancock Center is in a commercial district, while the Sears Tower is in the financial district. The Hancock Center 94th floor observation deck displays exhibits about the city of Chicago. Maps explain the view in each direction and a special meshed-in area allows the visitors to feel the winds 314 m (1,030 ft) above ground level. The 44th-floor skylobby features America's highest indoor swimming pool.

AT&T Corporate Center

The AT&T Corporate Center is the 4th tallest completed skyscraper in Chicago in Cook County, Illinois, United States and the 9th tallest in the United States at a height of 1,007 ft (307 m) containing 60 floors. Completed in 1989, the 1.7 million square foot (158,000 m²) supertall building stands two blocks east of the Chicago River and northeast of the Sears Tower at 227 West Monroe Street (100 South Franklin alternate address) in the Loop community area of downtown Chicago. Composed of retail and commercial office space, the tower is the tallest building constructed in Chicago in the last quarter of the 20th century.The building was built to consolidate American Telephone & Telegraph Company central regional headquarters offices.

Aon Center

The Aon Center (200 East Randolph Street) is a modern skyscraper in Chicago designed by architect Edward Durell Stone and completed in 1973 as the Standard Oil Building. With 83 floors and a height of 346 m (1,136 ft), it is the second tallest building in Chicago, surpassed in height only by the Sears Tower. It is the third tallest in the United States behind the Empire State Building and the 15th tallest in the world. The building is managed by Jones Lang LaSalle.

Sears Tower

The Sears Tower is a skyscraper in Chicago, Illinois. It has been the tallest building in the United States since 1973, surpassing the World Trade Center, which itself had surpassed the Empire State Building only a year earlier. Commissioned by Sears, Roebuck and Company, it was designed by chief architect Bruce Graham and structural engineers Srinivasa and Fazlur Khan of Skidmore, Owings and Merrill.

Construction commenced in August 1970 and the building reached its originally anticipated maximum height on May 3, 1973. When completed, the Sears Tower had overtaken the roof of the World Trade Center in New York City as the world's tallest building. The tower has 108 stories as counted by standard methods, though the building owners count the main roof as 109 and the mechanical penthouse roof as 110. The distance to the roof is 442.3 metres (1,451 ft), measured from the east entrance.

In February 1982, two television antennas were added to the structure, increasing its total height to 520 m (1,705 ft). The western antenna was later extended to 527.3 metres (1,730 ft) on June 5, 2000 to improve reception of local NBC station WMAQ-TV.

Black bands appear on the tower around the 29th–32nd, 64th–65th, 88th–89th, and 104th–109th floors. These are louvers which allow ventilation for service equipment and obscure the structure's belt trusses which Sears Roebuck did not want to be visible as on the John Hancock Center. The Sears Tower has the second most total floor space of any building in the United States, only behind The Pentagon.

The building's official address is 233 South Wacker Drive, Chicago, Illinois 60606.

On August 12, 2007, the Burj Dubai in Dubai, United Arab Emirates was reported by its developers to have surpassed the Sears Tower in all height categories. It overtook the Sears Tower antenna (527.3 m) and the building now currently stands at least 37.6 metres taller (564.9m).