List of tallest buildings in Chicago

Chicago, the third-largest city in the United States, is home to 1,264 completed high-rises, 44 of which stand taller than 600 ft. The tallest building in the city is the 108–story Willis Tower (formerly 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 from its completion, and remained the tallest building in the United States until May 10, 2013 when it was overtaken by One World Trade Center in New York City. The second-, third- and fourth-tallest buildings in Chicago are the Trump International Hotel & Tower, the Aon Center and the John Hancock Center, respectively. Of the ten tallest buildings in the United States, four are located in Chicago. , the entire city has 105 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, a considerable height in the 1800s, to a height of 138 ft, making it the tallest building in the world. 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 11 of the city's 91 tallest buildings were constructed. The city then went through an even much 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, including the Trump International Hotel and Tower. there were 67 skyscrapers under construction in Chicago.

Tallest buildings
This list ranks Chicago skyscrapers that stand at least 550 ft tall, based on standard height measurement. 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.

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.

Proposed
This lists buildings that are proposed for construction in Chicago and that are planned to rise at least 325 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 or Distressed
* Table entries with dashes (—) indicate that information regarding expected building heights, floor counts or dates of completion has not yet been released.

Timeline of tallest buildings
This is a list of buildings that once held the title of tallest building in Chicago. Of all the buildings that have held the title, only Willis Tower has also held the title of world's tallest building.