Chicago, the third-largest city in the United States, is home to 1,397 completed high-rises, 56 of which stand taller than 600 ft. The tallest building in the city is the 110-story Willis Tower (also known as the Sears Tower), which rises 1451 ft in the Chicago Loop and was completed in 1974. Sears Tower was the tallest building in the world upon its completion, and remained the tallest building in the United States until May 10, 2013. The second, third, and fourth-tallest buildings in Chicago are the Trump International Hotel & Tower, St Regis Chicago, and the Aon Center, respectively. Of the ten tallest buildings in the United States, two are located in Chicago, and of the fifteen tallest buildings in the United States, five are in Chicago. Chicago has the second-tallest skyline in the United States after New York City, and leads the nation in the twenty tallest women-designed towers in the world, thanks to contributions by Jeanne Gang and Natalie de Blois. , Chicago had 125 buildings at least 500 ft tall. Chicago is the birthplace of the skyscraper. The Home Insurance Building, completed in 1885, is regarded as the world's first skyscraper. This building used the steel-frame method, innovated in Chicago. It was originally built with 10 stories, an enormous height in the 1800s, to a height of 138 ft. It was later expanded to 12 stories with a height of 180 ft. The building was demolished in 1931. New York City then began building skyscrapers as Chicago had done, and the two cities were virtually the only cities in the world with huge skylines for many decades. Chicago has always played a prominent role in the development of skyscrapers and three past buildings have been the tallest building in the United States. Being the inventor of the skyscraper, Chicago went through a very early high-rise construction boom that lasted from the early 1920s to the late 1930s, during which nine of the city's 100 tallest buildings were constructed. The city then went through an even larger building boom that has lasted from the early 1960s. The tallest buildings are concentrated in various downtown districts such as the Loop, Streeterville, River North, the South Loop, and the West Loop. Other high-rises extend north along the waterfront into North Side districts such as the Gold Coast, Lincoln Park, Lakeview, Uptown and Edgewater. Some high-rises also extend south from downtown along the waterfront to South Side districts such as Kenwood, Hyde Park, and South Shore. Several new skyscrapers were constructed in the city throughout the 2000s and 2010s, including the Trump International Hotel and Tower, St Regis Chicago, NEMA Chicago, and Aqua. As of January 2021, there were 19 skyscrapers proposed or under construction, including One Chicago Square, 1000M, and Bank of America Tower, as well as Tribune Tower East, an approved skyscraper set to become the city's second-tallest building.

Tallest buildings

This list ranks completed Chicago skyscrapers that stand at least 550 ft tall, based on standard height measurement. There are no buildings in Illinois outside of downtown Chicago that exceed that height. This height includes spires and architectural details but does not include antenna masts. An equal sign (=) following a rank indicates the same height between two or more buildings. The "Year" column indicates the year of completion.

Tallest buildings by pinnacle height

This list ranks Chicago skyscrapers based on their pinnacle height, which includes radio masts and antennas. Standard architectural height measurement, which excludes antennas in building height, is included for comparative purposes. The "Year" column indicates the year in which a building was completed.

Tallest under construction or proposed

Under construction

This lists buildings that are under construction in Chicago and are planned to rise at least 300 ft. Buildings whose construction is on-hold are also included. A floor count of 30 stories is used as the cutoff for buildings whose heights have not yet been released by their developers. The "Year" category denotes when the building is expected to be completed.

Approved and proposed

This lists buildings that are proposed for construction in Chicago and that are planned to rise at least 300 ft. A floor count of 50 stories is used as the cutoff for buildings whose heights have not yet been released by their developers. The "Year" category denotes when construction of the building is expected to begin.

Cancelled

This lists buildings designed to rise at least 800 ft that were approved for construction in Chicago but were cancelled prior to completion. This list does not include vision projects such as Gateway Tower or the Miglin-Beitler Skyneedle, nor does it include projects that were not approved by the Chicago Plan Commission such as the Waldorf-Astoria Hotel and Residence Tower.

Timeline of tallest buildings

Honorable mentions