View the republished content from Orbitz' list complete with an interactive timeline of Chicago's tallest buildings.
Home Insurance Building, 1885 - 138 ft.
The Home Insurance Building had the honor of being the world's first skyscraper. Completed in 1885, it was designed with a fireproof steel frame, a revolutionary architectural feat at the time. It was demolished in 1931, by which time it had gained two extra floors and an added height of 42 ft.
Monadnock Building, 1893 - 197 ft.
The Monadnock Building is known for the distinctive architectural split between its north and south halves. The north half, completed in 1891, was built with traditional thick brick walls to support its 16-story height. The south half, completed two years later, is supported by a steel skeleton frame and topped by an ornate copper cornice.
Wrigley Building, 1924 - 438 ft.
The Wrigley Building, situated on the north bank of the Chicago River, was originally built to serve as the headquarters for the Wrigley Company. Its two towers - joined by walkways - are clad with 250,000 terracotta tiles in varying shades of white, each occasionally hand-washed to keep them looking their best.
Tribune Tower, 1925 - 463 ft.
The Tribune Tower's eye-catching architecture is the result of a competition held by the Chicago Tribune newspaper in 1922. The winning design was controversial at the time for its Gothic features, including ornate gargoyles and buttresses. A collection of stones from sites around the world - such as the Great Pyramid - are famously embedded into the walls of the tower.
35 East Wacker, 1927 - 523 ft.
35 East Wacker - or the Jewelers Building - was once one of the tallest buildings in the world. It housed the offices of jewelry merchants and dedicated 23 floors to garage space for their cars. A lift on the outside of the building would transport the drivers and their precious jewels up to their offices to reduce the risk of being burgled on the street outside.
Carbide & Carbon Building, 1929 - 503 ft.
The Carbide & Carbon Building was built in 1929 for the Union Carbide and Carbon Co. Its extravagant Art Deco design - rumored to emulate a champagne bottle - includes a polished black granite exterior and gold leaf, marble and bronze detailing. A sister building was planned but was canceled due to the devastating market crash of 1929.
Chicago Board of Trade Building, 1930 - 605 ft.
The Chicago Board of Trade Building opened in 1930 at a staggering height of 605 ft - the tallest in Chicago for over 30 years until the Richard J. Daley Center was built. Hugely recognizable, the building is considered a masterpiece in Art Deco design and features iconic details such as the 31 ft aluminum statue of Ceres - Roman goddess of agriculture - standing on top of the building.
One Prudential Plaza, 1955 - 601 ft.
Completed in 1955, One Prudential Plaza was the first skyscraper to be built in Chicago after the Second World War. It reaches a height of 601 ft, which at its completion made it the building with the tallest roof in the city. Despite its 'ugly' appearance, the building drew the interest of Barack Obama, who based his 2012 re-election campaign at the skyscraper.
Marina City, 1964-1968 - 599 ft.
Often likened to corn on the cob, these uniquely designed twin skyscrapers were, at the time of their completion, the tallest residential buildings in the world. Each of the Modernist buildings reach 65 stories and were designed by architect Bertrand Goldberg to contain as few right angles as possible.
Lake Point Tower, 1968 - 645 ft.
The Lake Point Tower has won awards for its unique and eye-catching architecture. It stands 70 stories tall on the Lake Michigan lakefront and was once the tallest residential building in the world. Its design was influenced by world-renowned Modernist architect Mies van der Rohe's unbuilt (and much smaller) concept for an office in Berlin.
875 North Michigan Avenue, 1969 - 1,128 ft.
875 North Michigan Avenue, also known as the John Hancock Center, is one of the most famous skyscrapers in Chicago. Measuring 1,128 ft, it is currently the fourth-tallest building in the city and the ninth in the United States. The elevators to the observation deck are some of the fastest in the world, capable of reaching speeds of about 20mph.
CNA Center, 1972 - 601 ft.
The CNA Center, also known as 'Big Red', was completed in 1972 and is well-known for its striking red color, which covers the exterior and many interior features of the building. On special occasions, the lights in the building are timed by a computer program to display messages.
The Aon Center, 1973 - 1,136 ft.
The Aon Center is the third-tallest building in Chicago and was the tallest building in the city at the time of its completion in 1973. The building's facade was originally clad in marble, but this was removed and replaced with white granite in the early 1990's following safety concerns. Its been renamed several times since its completion, but the nickname 'Big Stan' has stuck around since its days as the Standard Oil Building.
330 North Wabash / AMA Plaza / IBM Building, 1973 - 695 ft.
This monolithic building, also known as the IBM Building, measures a breathtaking 695 ft tall. It was designed by the world-renowned architect Ludwig Mies van der Rohe before he died in 1969 and is composed of the glass and steel that was his trademark. In 2010 it was added to the National Register of Historic Places, making it the newest building in Chicago on that list.
Willis Tower / Sears Tower, 1974 - 1,451 ft.
The Willis Tower, often called the Sears Tower, is perhaps the most famous of all the Chicago skyscrapers. Second-tallest in the Western Hemisphere, this building reaches a height of 1,451 ft and contains 110 stories. Its unique architecture is the result of its bundled tube structure, an innovation of designer Fazlur Rahman Khan and the first of its kind.
Crain Communications Building, 1983 - 582 ft.
The Crain Communications Building was completed in 1983 and is 41 stories high. Its unusual design - including a slanted roof and split down the center of the building - makes it one of the most unique skyscrapers in Chicago, and has earned it nicknames such as the 'Diamond Building' because of its diamond-shaped roof.
NBC Tower, 1989 - 627 ft.
The NBC Tower is one of the most famous skyscrapers in the city, notable for its striking Art Deco design with architectural features echoing those of the Tribune Tower and New York City's famous 30 Rockefeller Plaza. It rises 627 ft into the air and houses the offices and studios of NBC.
Two Prudential Plaza, 1990 - 995 ft.
Two Prudential Plaza is 995 ft tall, making it the sixth-tallest building in Chicago. Completed in 1990, its distinctive features include a pyramid-like peak and an 80 ft spire, without which it would still remain taller than One Prudential Plaza (which it is attached to). It is often recognized as one of the most beautiful skyscrapers in the city.
Aqua Tower, 2009 - 859 ft.
Completed in 2009, Aqua Tower has won many awards for its stunning architecture. Its rippling, watery appearance is the result of curved balconies of varying sizes on each story, inspired by the topography of nature and nearby Lake Michigan. It's also one of the tallest skyscrapers in the world to have been designed by a woman-led architectural firm.
150 North Riverside, 2017 - 724 ft.
150 North Riverside Plaza was completed in 2017. Its unique, top-heavy shape - garnering it nicknames such as 'the guillotine' - is the result of building on a small and technically troublesome plot; the first eight stories rise outwards at an angle from the base and then the building continues upwards traditionally for the rest of its 54-story height.
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