Famous for its landscapes, food, and contributions to the world of architecture, Chicago is a must-see destination with many attractions to visit. Whether you’re planning a move or a short vacation to the Windy City, you need to see at least a third of its most famous buildings. In this article, we share some of our favorites and interesting facts about each one.

Willis Tower

Formerly known as the Sears Tower, the Willis Tower was the tallest building in the world for decades and had the tallest roof in the Western Hemisphere until 2014. The 110-story, 1450-foot tower was completed in 1973 and remains Chicago’s tallest building. A multimillion-dollar renovation in 2009 greatly enhanced the building’s observation deck, now called Skydeck Chicago. Here, visitors can enjoy an interactive experience that teaches them about our city’s rich history while taking in the incredible view. 

The Chicago Skyline on a sunny day along the river walk.

Aqua Tower

One of Chicago’s most impressive buildings, Aqua Tower captivates visitors with its intricately designed terraces that mimic the undulating movement of water. This multiuse building, completed in 2009, has won several awards and continues to be a hot topic among tourists and design enthusiasts. The 80-story building also houses the Radisson Blu Aqua Hotel and a large terrace with pools, walking and running paths, gardens, hot tubs, and a fire pit. 

875 North Michigan Avenue

Completed in 1969 and formerly known as the John Hancock Center, 875 North Michigan Avenue is one of the world’s most iconic buildings. Its distinctive industrial design set a precedent at a time when structural expressionism was not openly celebrated. This 1,500-foot building (including twin antennas) boasts a 360-degree view of the city of Chicago, and visitors have access to that view in The Signature Room. 

Like Skydeck Chicago, The Signature Room offers visitors a fine dining experience with breathtaking views of the Chicago skyline and Lake Michigan. In addition, visitors can experience TILT, a platform that tilts you over Michigan Avenue from the 94th floor.

Tribune Tower 

In 1922, the Chicago Tribune newspaper held a competition to find someone who could design the world’s most beautiful office building. And it was John Mead Howells and Raymond Hood’s neo-Gothic design that impressed the judges and made the final cut. In addition to its beautiful and opulent design, the building incorporates pieces of some of the world’s most important structures into its exterior, including the Great Pyramid of Giza, the Great Wall of China, Bunker Hill, and the Taj Mahal. 

Marina City

Located in downtown Chicago, Marina City is a condominium complex known for its two cylindrical towers that resemble corncobs. At the time of completion, they were the tallest residential buildings and the tallest reinforced concrete structures in the world. In addition to residential units, Marina City is also home to House of Blues Chicago and Hotel Chicago. The former is a live music venue where guests can experience a rock and blues-themed environment, while the latter is a luxury Marriot Hotel.

Rookery Building

Completed in the 1880s and located in Chicago’s downtown financial district, the Rookery Building is the only remaining skyscraper from that era in Chicago. The building is listed on the National Register of Historic Places and has been a Chicago landmark since 1972. Visitors can book a tour with the Chicago Architecture Center to learn more about the rich history behind this remarkable skyscraper. You’ll also have access to the architects’ magnificent library on the 11th floor.

Wrigley Building

Located across from the Tribune Tower and overlooking the Chicago River, the Wrigley Building is one of Chicago’s most iconic buildings and dates back to the 1920s. It consists of two towers — a 30-story south tower and a 21-story north tower connected by a 14th-floor walkway. The Wrigley Building was Chicago’s first air-conditioned office building and one of the first skyscrapers in the area. The building’s proximity to the Chicago Riverwalk allows visitors to continue their exploration by walking along the 1.25-mile-long stretch of restaurants and niche shops. 

Chicago Cultural Center

When it opened in 1897, the Chicago Cultural Center housed the city’s public library and was the basement of the Grand Army of the Republic. This iconic building is a Chicago landmark and is listed on the National Register of Historic Places. In 1991, however, the building’s purpose was altered, and it became the nation’s first free cultural center, offering free exhibits, concerts, and artistic activities year-round. The building boasts a Classical Revival style inspired by the structures of ancient Greece and Rome. 


Formerly known as the Merchandise Mart, TheMART is a two-city block building with its own zip code and 4 million feet of space. It was built in 1930 to serve as a diverse marketplace where retailers could get all their goods. Today, TheMART is a multipurpose building that houses several technology companies and is home to Chicago’s largest multimedia video art exhibit.

The Aon Center

Completed in 1973, the Aon Center is one of Chicago’s tallest skyscrapers, the third tallest in the city. It was originally named the Standard Oil Building and colloquially known as the Big Stan. It was renamed the Amoco Building before becoming the Aon Center. This modern building was wrapped in over 43,000 slabs of Italian Carrara marble for years before the marble began to fall off, and the building was deemed unsafe. Today, white granite adorns the building’s exterior. A new project is underway to create an observatory and restaurant for visitors. 

Ready To Explore Chicago’s Most Famous Buildings?

If there’s one thing Chicago is known for, it’s impressive buildings. The city has 126 skyscrapers, making it the city with the second-most skyscrapers in the country, next to New York City. So wanting to explore and learn about the history behind them is totally understandable (and encouraged). Here at American Auto Insurance, we’re on a mission to get everyone to love Chicago as much as we do. And if you ever need low-cost auto insurance, we’re here for you. Contact us and a member of our team will be in touch shortly. 

Chicago Skyline by Kimberly Vardeman is licensed with CC BY 2.0


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