
Did you know the Home Insurance Building of Chicago was the world’s first skyscraper? This is the reason Chicago is known as the birthplace of skyscrapers. The construction of the building was completed in 1885 and was initially built with 10-stories, an enormous height in the 1800s. Later two more stories were added to this already giant skyscraper. But in 1931, the building was demolished. Even today, the skyscrapers in Chicago are inspiring the other metropolises to embellish their skyline with mega-structures.
World-renowned architectural firms like Gill on Board, Vinoly, Pelli, Jahn, Stern are raising the bar of Chicago's next-gen high-rise buildings. Today, Chicago's charismatic skyline features some of the most impressive skyscrapers globally. Willis Tower, Trump International Hotel and Tower, Aon Center, Franklin Center, and John Hancock Center are some of the tallest buildings in Chicago.
Nestled on the western shores of Lake Michigan, the paradigm shift of Chicago from a small trading outpost to America's third-largest city is prodigious. After World War I, Chicago began to expand, and in the later decades, the Chicagoan skyline we know today began to take shape.
Here are some iconic high-rise buildings of Chicago that contribute to making the 'Windy City' invincible ruler of urban structures. Also, you can read Chicago, Illinois Travel Guide for complete information about the city.
Willis Tower

Chicago’s tallest and one of the world’s loftiest buildings, Willis Tower, is a 108 story skyscraper. Formerly known as Sears Tower Chicago, the construction of this high-rise was completed in 1974 and surpassed New York’s World Trade Center to become the tallest building in the world. The building is still considered Chicago’s iconic landmark, and the black glass, steel exterior, and twin white spires are instantly recognizable from anywhere in the city.
Tourists visit this iconic skyscraper to enjoy the 70-second elevator ride to the 103rd-floor Skydeck, where they are greeted by the breathtaking views extending as far as Michigan and Wisconsin on clear days. The Skydeck features glass-bottom balconies that let you feel like floating in the air.
Note: If you plan to visit the Skydeck, tickets should be booked online in advance.
John Hancock Center

The second-largest building of Chicago is standing just right behind Willis Tower. It is a 1,128 feet high building with 100 floors, making it one of the most spacious buildings in Chicago. Its name was changed to 875 North Michigan Avenue in 2018, but people still call it John Hancock Center. Like Willis Tower, it also has an observatory deck that offers a 360° view of Chicago. The breathtaking views from the 94th-floor in many ways surpass those at the Willis Tower. Moreover, the floor-to-ceiling windows tip out over the ground as you stand there, giving you an adrenaline rush.
The John Hancock Center's Observation Deck is home to TILT, Chicago's highest thrill ride if you are an adventure enthusiast.
Tribune Tower

The 36-storied, famed neo-gothic skyscraper on Michigan Avenue near Chicago River is Chicago’s most treasured historic landmark. The DuSable Bridge near the Chicago Tribune Tower provides an excellent view of the surrounding buildings, offering a sense of Chicago’s urban life. The tower was once home to Chicago Tribune and WGN Radio until WGN Radio left in 2018.
Just like its Neo-Gothic exterior, the story behind Tribune Tower’s origin is also interesting. In 1922, on the occasion of Chicago Tribune’s 75th anniversary, the Chicago Tribune newspaper organized an international competition for a new headquarters in Chicago. More than 260 entries from 23 countries all across the globe participated in the competition, making it the most significant architectural competition in the USA. The winner was New York-based architect duo John Mead Howells and Raymond Hood, who designed the neo-gothic style building.
The Aon Center

Formerly known as Amoco Building, the Aon Center in Chicago Loop is designed by architect firms Edward Durell Stone and the Perkins and Will partnerships. The construction of the supertall skyscraper was completed in 1974. With over 83 floors, it is the fourth-largest building in Chicago. Furthermore, it was a former home to the world headquarters of Aon and Amoco and oc-headquarters of Kraft Heinz.
The modern design of the building comprises a tubular steel-framed structure, and on a clear day, the skyscraper is easily spotted from the edge of Millennium Park. Besides, just like Willis Tower and John Hancock Center, The Aon Center is constructing its observation deck that will feature a Chicago skyscraper glass floor thrill ride.
James R. Thompson Center

James R. Thompson Center, formerly known as the State of Illinois Center, was completed in 1985 and served as the second capitol for the State of Illinois. It is one of the biggest towers in Chicago. This postmodern style civic building was designed by famous architect Helmut Jahn and housed several important offices of the Illinois State Government. Besides, the transparency of the building symbolizes the state’s commitment to serving people. This prominent postmodern architecture comprises a sloping glass design that gives the impression of ring segments. You are greeted by a colossal atrium clad with skylights when you enter the building. The theme of the building is ‘Openness and transparency', where government businesses are conducted in full public view.
How to find skyscraper condo/apartment to live in Chicago
There are a few things to keep in mind when searching for a skyscraper condo in Chicago. The first is budget. What can you afford? Keep in mind that downtown prices will be higher than those in the suburbs. The second is location. Do you want to be in the heart of the city or do you prefer a quieter neighborhood? Once you've decided on your budget and location, it's time to start your search!
The best place to start your search is online. There are a number of websites that focus on Chicago real estate. Make sure to use keyword like "skyscraper condo" and "Chicago condo for sale" to get the most relevant results. Another great resource is your local paper's real estate section. This is a good way to get an idea of what's on the market and see if anything catches your eye.
Wrap Up
Being the birthplace of skyscrapers, the Windy City is home to some of the world's tallest and most magnificent skyscrapers. Behind the rise of skyscrapers in Chicago, there is a story of struggle and innovation. When a massive fire broke out in 1871, a large part of Chicago was destroyed, and many were left homeless and destitute. It is when the Chicagoans came up with the idea to rebuild their home into something better and more secure than before. Today, Chicago's skyline itself is an iconic landmark of the USA.