Home Insurance Building in the context of Chicago window

The world's first skyscraper was built in Chicago in 1885. Since then, the United States has been home to some of the world's tallest skyscrapers. New York City, and especially the borough of Manhattan, has the tallest skyline in the country. Eleven American buildings have held the title of tallest building in the world. New York City and Chicago have been the centers of American skyscraper building. The 10-story Home Insurance Building, built in Chicago in 1885, is regarded as the world's first skyscraper; the building was constructed using a novel steel-loadbearing frame which became a standard of the industry worldwide.

Since its topping out in 2013, One World Trade Center in New York City has been the tallest skyscraper in the United States. Its spire brings the structure to a symbolic architectural height of 1,776 feet (541 m), connoting the year the Declaration of Independence was signed, though the absolute tip (or pinnacle) of the structure is measured at 1,792 ft (546 m). However, the observation deck elevation and the height to the highest occupied floor of One World Trade Center are surpassed by Central Park Tower, 432 Park Avenue, 111 West 57th Street, and Chicago's Willis Tower, which was formerly and is still commonly known as Sears Tower. Tribune East Tower in Chicago, 350 Park Avenue, and 175 Park Avenue, in New York City will also have higher occupied floors and roofs upon their completion.

The earliest stage of skyscraper design encompasses buildings built between 1884 and 1945, predominantly in the American cities of New York and Chicago. Cities in the United States were traditionally made up of low-rise buildings, but significant economic growth after the American Civil War and increasingly intensive use of urban land encouraged the development of taller buildings beginning in the 1870s. Technological improvements enabled the construction of fireproofed iron-framed structures with deep foundations, equipped with new inventions such as the elevator and electric lighting. These made it both technically and commercially viable to build a new class of taller buildings, the first of which, Chicago's 138-foot (42 m) tall Home Insurance Building, opened in 1885. Their numbers grew rapidly, and by 1888 they were being labelled "skyscrapers".

Chicago initially led the way in skyscraper design, with many constructed in the center of its financial district during the late 1880s and early 1890s. Sometimes termed the products of the Chicago school of architecture, these skyscrapers attempted to balance aesthetic concerns with practical commercial design, producing large, square palazzo-styled buildings hosting shops and restaurants on the ground level and containing rentable offices on the upper floors. In contrast, New York's skyscrapers were frequently narrower towers which, more eclectic in style, were often criticized for their lack of elegance. In 1892, Chicago banned the construction of new skyscrapers taller than 150 feet (46 m), leaving the development of taller buildings to New York.

William Le Baron Jenney (September 25, 1832 – June 14, 1907) was an American architect and engineer known for building the first skyscraper in 1884.

In 1998, Jenney was ranked number 89 in the book 1,000 Years, 1,000 People: Ranking the Men and Women Who Shaped the Millennium.