Chicago is the birthplace of skyscrapers, and also a renowned concrete jungle filled with dozens of iconic towers.
As early as the 1970s, the city already had three skyscrapers exceeding 300 meters (984 feet) in roof height, a remarkable achievement at a time when almost no other cities in the world had reached such heights. Among them, the Sears Tower had been the tallest building in the world for more than two decades until 1998, when the spires of the Petronas Towers surpassed it. It also remained the tallest building in the United States for an even longer period, until 2012, when the antenna of One World Trade Center exceeded its height. However, both One World Trade Center and Petronas Towers are shorter than Sears Tower by roof height, which is a measurement that is more favored by the majority of skyscraper enthusiasts. As of 2026, Sears Tower (now called Willis Tower) ranks 2nd among all the completed skyscrapers in America by roof height, only after the Central Park Tower in New York City, which surpassed its roof height in August 2019.
The number of buildings exceeding 300 meters in roof height in Chicago had consistently been ahead of other American cities, including New York City, until 2014. At that time, Chicago had four such skyscrapers, far more than New York City, which had only one building with a roof height exceeding 300 meters.
As of 2026, Chicago is home to 38 completed buildings taller than 200 meters (656 feet), the second-highest total in North America after New York City. The city also boasts seven completed skyscrapers exceeding 300 meters (984 feet) in architectural height. With such an extraordinary number of skyscrapers, Chicago is the only American city besides New York that truly deserves the title of a concrete jungle.
Below is a list of the tallest buildings in Chicago, the buildings are at least 300 meters or 984ft by standard height.
1. Willis Tower
Standard height: 442 meters (1451ft) Total height: 527 meters (1729ft)
Built in 1973 as Sears Tower, the tower was the world's tallest building from 1973 to 1998, and was the tallest in America from 1973 to 2014. It's now the 3rd tallest building in America, after One World Trade Center and Central Park Tower in New York City, however, its roof and observation deck are all higher than that of One World Trade Center.
The tower was developed by Sears Group as the headquarters of the company. In 1994, Sears sold the tower and the company's naming rights expired in 2003. Willis Group leased a considerable amount of office space in the tower in 2009, and obtained the naming rights through negotiations, the tower was renamed as Willis Tower in the same year.
The 103rd floor of the tower has an observation deck, offering 360 degree view of the city from a height of 1353ft. More details of Willis Tower.
2. Chicago Trump International Hotel & Tower
Standard height: 423 meters (1388ft) Roof height: 356 meters (1171ft)
Year built: 2009
Architect: Adrian Smith (SOM)
Chicago Trump International Hotel & Tower
Trump International Hotel & Tower is named after the real estate tycoon and 45th US President Donald Trump, the tower is the tallest among all the buildings named after Trump.
The Trump Tower is located next to the main branch of the Chicago River, and just east of the iconic Marina City twin towers and IBM Building.
The tower was designed by Adrian Smith, the architect behind the current world's tallest building Burj Khalifa. And it was also intended to become the world's tallest building when it was proposed in 2001, but Donald Trump gave up the idea after the September 11 attacks, and in 2005 he planned to make the building higher than the Sears Tower but shorter than the Petronas Towers (the world's tallest buildings by that time), so it could still become the tallest building in America. However, the city's mayor was against that height, the tower was eventually scaled down to its current height.
The tower is mixed-used, floors below 12th floor are retail space and parking garage, 17th to 27th floors are occupied by a hotel with 339 rooms, and 28th to 89th floors are occupied by 486 residential condominiums, the penthouse at 89th floor briefly held the title of the highest residence in the world before the completion of the Burj Khalifa.
3. The St. Regis Chicago
Standard height: 363 meters (1191ft)
Year built: 2020
Architects: Studio Gang Architects
Developer: Wanda Group; Magellan Development Group
The St. Regis Chicago
Previously known as Vista Tower or Wanda Vista, the St. Regis Chicago is a mixed-use building developed by Magellan Development Group in joint with the Chinese developer Wanda Group, the building contains a 5-star hotel with 210 guest rooms, and residential space with 406 condominiums.
The building is designed by architect Jeanne Gang, it replaced the nearby Aqua Tower (also designed by Jeanne Gang) as the tallest building in the world designed by a woman. The building is composed of three connected towers of different heights, and each tower is composed of a series of stacked frustum-shaped structures, making the whole building appears like flowing water, similar to the nearby Aqua Tower.
4. Aon Center
Standard height: 346 meters (1136ft)
Roof height: 346 meters
Year built: 1973
Architects: Edward Durell Stone, Perkins + Will
Developer: Standard Oil of Indiana
Aon Center
Built in 1973, Aon Center was the tallest building in Chicago at its completion, and was also the tallest in the world outside of New York City.
The building was originally named Standard Oil Building, as it was built as the headquarters of the Standard Oil Company. In 1985, Standard Oil Company was renamed as Amoco, and changed the building's name to Amoco Building. In 1999, Aon Corporation signed as the primary tenant of the building and obtained the building's naming rights, so Amoco Building was renamed as "Aon Center", which is still in use today.
The building's facade is comprised of an upward flow of columns, kind of similar to that of the former World Trade Center twin towers.
The latest owners of the building acquired it in 2015, and plans to add a multi-level observatory to the building's uppermost floors and the roof, and will include a tallest exterior elevator in the world.
A render of Aon Center after renovation
If completed, Chicago would have a total of 3 skyscrapers that contain observatories, currently only Shanghai, New York City, and Tokyo have more such kind of skyscrapers.
However, the project was suspended in 2020 due to the COVID-19 pandemic. There were plans to move forward the project at one point, but it was ultimately shelved indefinitely due to the slump in the tourism industry and funding issues.
5. 875 North Michigan Avenue (formerly John Hancock Center)
Standard height: 344 meters (1127ft)
Total height: 457 meters (1500ft)
Year built: 1969
Architects:Skidmore, Owings & Merrill
Developer: Jerry Wolman Associates
875 North Michigan Avenue
Upon its completion in 1968, the building was the second tallest building in the world, only after the Empire State Building in New York City, but if the height is measured to the tip of antennas, it's taller than the Empire State Building.
Before Feb 2018, the building was known as John Hancock Center, named for John Hancock Insurance Company, which co-developed the building and financed its construction, and was also its primary tenant. John Hancock's naming rights expired in 2013, and the name was removed in early 2018. Since then, the building has been temporarily known by its address, 875 North Michigan Avenue, and is expected to receive a new name if a future tenant acquires the naming rights.
The building was designed by Skidmore, Owings & Merrill, which also designed the Sears Tower, both buildings are cladded with black-colored glass and have a pair of antennas installed on the top, the antennas act as transmitters for television stations. A distinctive feature of the tower is those X-shaped structures on the facades, they make the tower more resistant to wind loads, and also reduce the needs of interior columns, allowing the building's floor plates to have more occupiable space.
The 100-story building is in mixed use, floors below 43rd floor are office spaces, 44th to 92nd floors are used for residences, the uppermost one of which was once the highest residence in the world before it was surpassed by the penthouse on the city's Trump Tower. The 94th floor is occupied by an observation deck called 360 Chicago, it's 1030 ft high from the ground, not as tall as that of the Willis Tower, but its floor space is larger and is less crowed. 95th and 96th floors have a restaurant and a bar, the rest floors to the top are for mechanical uses.
6. Franklin Center
Standard height: 307 meters (1007ft)
Roof height: 270 meters (886ft)
Year built: 1989
Architect: Adrian Smith (SOM)
Developer: Stein & Company
Franklin Center
The Franklin North Tower was originally named AT&T Corporate Center, it was built by AT&T company to consolidate the company's central region headquarters. The building and its adjacent property was acquired by Tishman Speyer in 2004, and the property was later named as Franklin Center, the skyscraper is referred to as The Franklin North Tower.
7. Two Prudential Plaza
Standard height: 303 meters (995ft)
Roof height: 279 meters (915ft)
Year built: 1990
Architects:Loebl Schlossman Dart & Hackl
Developer: The Prudential Property
Two Prudential Plaza
Two Prudential Plaza is located just west of the Aon Center, the two buildings are situated very close. The building is iconic for its pyramidal crown, which is rotated 45 degree and topped with an 24-meter (80 ft) spire. Without the spire, it's 279 meters tall, about as tall as New York's Chrysler Building, which is 282 meters tall without the spire.
Developer: JDL Development; Wanxiang America Real Estate Group
One Chicago East Tower
One Chicago East Tower is the taller of the two towers in the One Chicago complex, formerly known as One Chicago Square, located in Chicago's River North neighborhood. The two towers are connected by a central podium.
The tower is primarily residential, containing 812 residential units, while the podium houses retail space. With a roof height of 296 meters (971 feet), it is just 4 meters short of the 300-meter threshold for a supertall skyscraper. By roof height, it is Chicago's sixth-tallest building, while by architectural height, it ranks eighth.
Proposals:
1. Tribune East Tower
Height: 433 meters (1422ft)
Estimated year top out: 2030 or later
Architect:Adrian Smith Developer: CIM Group
Tribune East Tower is a supertall skyscraper that is planned to be built on the east side of the Tribune Tower in the Streeterville area.
The original owner of Tribune Tower (Tribune Media company) had sold the tower and its adjacent property in 2016 (they moved their office to the above-mentioned Two Prudential Plaza in July 2018 ), the new owner CIM Group is a real estate developer that is best known for developed the supertall tower at 432 Park Ave in New York City.
In April 2018, the plan for a 1422ft tall tower on Tribune Tower property was unveiled, the new tower will surpass the Trump International Tower to become the second tallest building in Chicago, and is only 9 meters shorter than the Willis Tower. Similar to the city's Trump International Tower, Tribune East Tower will not be used as office space like most other buildings on this page, but will be mixed-used for residential units and hotels.
In October 2018, the plan for Tribune East Tower was approved by both Chicago Plan Commission and Chicago City Council.
Because of the Financial Crisis occurred many years ago, many great proposals for supertalls in Chicago were cancelled one after the other due to the financial difficulties. Some examples are Waterview Tower, Chicago World Trade Center and a more notable one, the Chicago Spire, which was once considered likely to be the next tallest building in America and also features a nice and special design.
Since then there was no obvious development on skyscrapers in the city while a large number of cities around the world are witnessing the skyscraper construction booms.
Skyline of Chicago, 4 Roof-height-supertalls can be easily picked out in the picture that much taller than the others.
Now the number of roof-height-supertalls in Chicago has been caught up by New York City since the completion of 432 park Ave, and is being transcended by New York, the disparity is likely to continue widening since there are numerous supertall skyscrapers planned in New York City.
Even so, the city's skyline is unique and attractive with a splendid natural scenery accompanied as the background, which is the view of the blue and extensive Michigan lake, that is invincible and can be hardly replaced by other cities. With its unique cityscape Chicago has been chosen as the city where many stories take place at by numerous movies.
Furthermore, in recent years some new skyscrapers have been proposed as the economy recovers, Chicago may once again receive a construction boom in several years.
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