Six Chicago Skyscrapers that Change the Architectural World

Chicago is home to a wide array of unique and stunning architecture. Credited as the birthplace of the first modern-day skyscraper in 1885, Chicago has long been a breeding ground for innovative designs and builds. After the Great Chicago Fire of 1871 came the Great Rebuilding period. Architects from all over flocked to the city for a chance to put their signature on a new Chicago skyline. The result of this rebuild is a stunning, diverse architectural masterpiece. Since this rebuild, Chicago has not stopped pushing the boundaries and achievements for architecture. At ArtRKL, we believe in celebrating architecture as its own form of art. Here are six Chicago skyscrapers that changed the architectural world.

Currently, the oldest skyscraper standing in Chicago, the Manhattan Building was built in 1891 by architect William LeBaron Jenney. Standing at 170 feet, this building is the oldest surviving skyscraper in the world to use only a skeletal supporting structure. The facade is crafted with a mix of granite and brick, giving the building its rustic brown hue. The building’s windows are adorned with intricate terracotta carvings, showing the deep craftsmanship of the building.

Though this may not be the flashiest building on the list, it’s important to keep in mind the historical context of when it was built. Jenney spent time debating whether he should aim for more height in his building or create a structure that gives the illusion of height. In the end, Jenney went for a wider frame with less height, as people at this time still were not used to tall buildings. Easing into this kind of architecture would begin to carve a path for the monstrously high buildings we are familiar with today.

This neo-gothic building stands out among the skyline with its buttresses and castle-esque design. Built by Howells & Hood in 1925, this building used to house the Chicago Tribune. Today it is home to luxury condos, but the beautiful stonework on the 463-foot building is carefully preserved, making the skyscraper a must-see sight on the Magnificent Mile. The building is beloved in the skyline for its unique design and homage to French castles. But the design of the Tribune Tower almost never happened.

In 1922, the Chicago Tribune hosted an international competition to design a new home base for the publisher. They were seeking “the most beautiful building in the world.” With a $100,000 cash prize—the equivalent of about $ 1.8 M today—the competition drew contestants from around the globe. What transpired was one of the first global architecture forums where citizens and architects alike were able to see each country’s version of a skyscraper, and the changing attitudes of what the American skyscraper could be were brought to the surface. The public conversation around architecture went on to continue influencing the drive for evolving skyscrapers not just in Chicago but around the world as well.

Chicago architecture is no stranger to the Art Deco movement, and the Chicago Board of Trade Building encapsulates everything we love about the movement. Completed in 1930, this 605-foot building still houses futures and options exchanges. In fact, it is the oldest exchange operation in the world. Built by Holabird & Root, this skyscraper captures the Egyptian influence in its pyramid-esque structure. Notice how each section sits atop the other, coming together at a point at the top. This building design gives the illusion of buildings reaching for the sky, a popular trick of Art Deco. At the top of this building sits a statue of the Roman goddess Ceres. Ceres was the goddess of agriculture and grains. Fitting, considering the Board of Trade originally dealt in the trade of wheat and corn.

A big part of Art Deco was the inclusion of decorative facades and special attention to aesthetics. Two carvings of men frame the entryway of the limestone building. One is an Egyptian man holding wheat, while the other is a Native American man holding corn. This, again, references the original trades of the building.

Debuting in 1968, these brutalist towers are not only a Chicago skyline staple but part of indie rock lore as well. The two towers are featured on the cover of Chicago-based band Wilco’s “Yankee Hotel Foxtrot.” It’s not surprising why Wilco would choose these two buildings as cover art, their unique “corn cob” structure stands out among the darker, rectangular buildings in the downtown loop. These residential towers stand at 587 feet tall, and in many ways were ahead of their time.

Architect Bertrand Goldberg built the towers at a time when many Chicagoans were flocking to the suburbs and leaving downtown residentially abandoned. The towers were meant to attract people back to downtown living and were marketed to middle-class citizens as a way to live where you play. The idea was to provide central housing close to entertainment, transportation, and retail. Goldberg also included ample space for residents to park their cars or boats (hence the name Marina City) to rival the amenities suburban living supplied. Today, the buildings are still residential and Goldberg would’ve loved to see that the Loop has become one of the quickest-growing neighborhoods for young professionals to live.

If you ask any Chicagoan they’ll tell you this building is still called the Sears Tower. Renamed in 2009, the Willis Tower is perhaps the most famous building on this list. Standing at a daunting 1,451 feet, this was once the tallest building in the world (as Ferris Bueller would tell you). This architectural behemoth is the design of architect Bruce Graham. It held the title of the tallest building in the world from its completion in 1973 until 1998, making it one of the most known buildings in the world.

Its innovative architecture paved the way for the next wave of skyscrapers we hear about breaking records today. A major draw of the Willis Tower is the Skydeck, an observation deck sitting on the 103rd floor of the building that features reinforced glass boxes that jut out over the side of the building, allowing brave visitors a chance to observe the city from 1,353 feet in the air. The skyscraper is built in the International Style of architecture which is defined by a minimalist facade and steel industrial building materials. The building is one of the most beloved skyscrapers in the city and has made appearances in nearly every movie about Chicago. Few buildings achieve such status as being a symbol for a city, but the Willis Tower transcends that role.

Rounding out our list is one of the newest members of the Chicago skyline. Opening in 2020, the St. Regis, designed by Jeanne Gang, is one of the most unique buildings in the skyline. The modernist building is designed to complement the surrounding water of the Chicago River and Lake Michigan, celebrating the natural beauty of the city. Noticeably, the building has a section that appears to be missing near the top. This is no mistake—this architectural design is called a blow-through floor and allows the wind to pass through the building, making it more structurally sound.

With a wave-like appearance, this 1,191-foot tall building marks the second building designed by Gang in the Chicago skyline. Her other, the Aqua Tower, was noted for being the tallest skyscraper built by a woman at the time of its completion, and she broke her own record with St. Regis. Gang was awarded the Charlotte Perriand Award in 2023, a prestigious award given to architects who are pushing innovation in the field of architecture. Gang isn’t done putting her signature in Chicago though, her next project is redesigning the Global Terminal at the O’Hare International Airport. 

This is just a glimpse at the magnitude of architecture Chicago has to offer. The diverse styles of buildings have consistently put Chicago at the top of best city skylines lists. The architecture of Chicago not only creates a beautiful city but a rich capsule of history spanning back hundreds of years. Chicago continues to make its architecture a beloved part of the city for residents and tourists alike. The next time you find yourself in the Windy City take a moment to look up and take in the architectural history surrounding you.

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