Tallest Buildings in Chicago Create The Most Unique Skyline

Chicago is the third most populated city in the US, so it also has some of the tallest and most memorable skyscrapers. The Chicago skyline is full of modern architecture, setting it apart from every other busy city.

Some of the tallest buildings in the US are in Chicago, including Willis Tower, Trump International Hotel and Tower, and St. Regis Chicago.

Why are Chicago Skyscrapers so Tall?

Tallest Buildings in Chicago

After New York, Chicago has the most skyscrapers in the US. It’s expensive to build structures that tall, and many of the lots in Chicago have expensive land values. So, it doesn’t take long for the buildings to earn enough money for the cost to be worth it.

For that reason, most tall buildings in Chicago are clustered together. You’ll find them concentrated in districts like the Loop, River North, Streeterville, the South Loop, and the West Loop. These areas also happen to be close to other big tourist attractions, which can help the properties earn more money.

What is the Tallest Building in Chicago?

Tallest Buildings in Chicago Create The Most Unique Skyline

Willis Tower, formerly known as Sears Tower, is the tallest building in Chicago. It’s also the most iconic, along with 875 North Michigan Avenue, because they each have two distinctive antennas.

Chicago Boroughs Tall Buildings

TopBuildingConstruction StatusYearAddressFloor AreaHeightObservatoryLifts/Elevators
#1Willis Tower Completed1974 233 S. Wacker Drive
Chicago, Illinois 60606
4,477,800 sq ft (416,000 m2)1,451 ft (442.2 m)1,353 feet (412.4 m)104
#2Trump International Hotel and Tower Completed2009401 N. Wabash Ave.
Chicago, Illinois
2.6 million sq ft (240,000 m2)1,388 ft (423 m)-27
#3St. Regis ChicagoCompleted2020363 East Wacker Drive, Chicago, Illinois1,414,000 sq ft (131,400 m2)1,198 ft (365 m)--
#4Aon Center Completed1973200 E. Randolph St.
Chicago, Illinois 60601
3,599,968 sq ft (334,448 m2)1,136 feet (346 m)planned construction50
#5875 North Michigan AvenueCompleted1969875 North Michigan Avenue2,799,973 sq ft (260,126 m2)1,127 ft (343.5 m)1,030 feet (310 m)50
#6Franklin Center Completed1989 227 West Monroe Street
Chicago, Illinois
1,699,987 sq ft (157,934.0 m2)1,007 ft (306.9 m)--
#7Two Prudential Plaza Completed1990180 N. Stetson Av.
Chicago, Illinois
1,399,986 sq ft (130,063.0 m2)995 ft (303.2 m)--
#8One Chicago East Tower Topped-out-1 West Chicago Avenue, Chicago, Illinois 60610-973 ft (296.5 m)--
#9311 South Wacker Drive Completed1990311 S. Wacker Drive
Chicago, Illinois
1,400,000 sq ft (130,000 m2)961 ft (292.9 m)--
#10NEMA ChicagoCompleted20191210 South Indiana Avenue
Chicago, Illinois 60606
-896 feet (273 m)--

Most of the other tallest Chicago buildings are near Willis Tower. They have a wide variety of uses, including tourist attractions, hotels, office spaces, apartments, and retail businesses.

Here are the tallest buildings in Chicago:

Willis Tower

Willis Tower Building

Height: 1,451 feet

Willis Tower was the world’s tallest building when it was built in 1974, and it held that title until 1998. Now, it’s the third tallest building in the US and the 26th tallest in the world. It was named the Sears Tower until 2009 when Willis Group Holdings gained naming rights.

It’s known for the famous Skydeck, which is a glass box visitors can walk into on the 103rd floor. The glass can withstand 5 tons of pressure and hold 10,000 pounds.

Trump International Hotel and Tower

Trump International Hotel and Tower

Height: 1,388 feet

Trump International Hotel and Tower is the 7th tallest building in the US. It was built in 2009 along the Chicago River. In 2001, it was planned to be the tallest skyscraper in the world, but the architects scaled it back after the 9/11 attacks.

The building has 2.6 million square feet of floor space, occupied by restaurants, hotel rooms, and luxury condos. Hotel guests can expect to pay $375 to $1,275 per night. The largest hotel rooms are the size of an average US house.

St. Regis Chicago

St. Regis Chicago

Height: 1,198 feet

St. Regis, formerly known as the Wanda Vista Tower, was completed in 2020 with 101 stories. It’s the 11th tallest building in the US and the tallest skyscraper ever designed by a woman. Architect Jeanne Gang designed it.

It has hotels and condos that overlook Lake Michigan. The top segment of the tower has some empty “blow-through” floors to reduce the swaying from the wind. There are also six tanks of water containing over 400,00 gallons to counteract the wind.

Aon Center

Aon Center

Height: 1,136 feet

Aon Center, formerly known as the Standard Oil Building and the Amoco building, is the 12th tallest US building. Construction finished in 1973, and it’s mostly occupied by office space. It was Chicago’s tallest building when it opened.

There are plans to add a $185 million observation deck, featuring a thrill ride called “Sky Summit.” The ride will include a glass box that lifts guests above the Chicago skyline. It was supposed to be done in 2022, but COVID postponed the plans by at least one year.

875 North Michigan Avenue

875 North Michigan Avenue

Height: 1,127 feet

875 North Michigan Avenue, more commonly known as the former John Hancock Center, has two massive antennas like Willis Tower. Each antenna is over 348 feet tall to transmit signals to nearby radios and TVs.

It was built in 1969, making it the world’s tallest building built in the 1960s. At the time, it was also the tallest outside of New York City to reach 1,000 feet. Today, it has a popular observation deck known as 360 Chicago. In 2014, a TILT attraction was added where guests lean on glass boxes that tilt toward the city.

Franklin Center

Franklin Center

Height: 1,007 feet

The Franklin includes two tall towers linked together. The taller of the two was built in 1989, and it was known as the “AT&T Corporate Center” at the time. In 1992, it was linked to the building next to it. Later, both buildings shared the name “The Franklin Center.”

It’s only 0.1 miles from Willis Tower, so it’s easy to spot in the Chicago skyline. Inside, you’ll find shops, restaurants, offices, and a parking garage.

Two Prudential Plaza

Two Prudential Plaza

Height: 995 feet

Two Prudential Plaza is the closest building to 1,000 feet without going over. It was built in 1990 next to One Prudential Plaza, formerly the Prudential Building Chicago. The two were connected in 1992, but Two Prudential Plaza is still the taller tower.

The two towers together are called “One Two Pru” with a total of 2.2 million square feet combined. The space is occupied by business offices, along with a few restaurants on the lower levels.

One Chicago East Tower

One Chicago East Tower

Height: 971 feet

One Chicago is a new apartment building completed in late 2021. It has an East and West tower, and the East Tower is about 400 feet taller. In April 2022, high winds caused a chunk of glass to fall from the structure, but luckily, no one was injured.

The luxury rentals can cost between $2,300 and $10,740 monthly. Residents get access to a fitness center, rooftop terrace, pool, and dog run.

311 South Wacker Drive

311 South Wacker Drive

Height: 961 feet

Chicago’s 9th tallest building is only a block away from Willis Tower. It can be distinguished by its crown-shaped top, which has 1,852 fluorescent tubes to shine colors on it at night.

311 South Wacker Drive has a 5-story “winter garden” lobby with a fountain, palm trees, and a curved glass ceiling. Pedestrians pass through the lobby because the building has access to Chicago’s expressways.

NEMA Chicago

NEMA Chicago

Height: 896 feet

NEMA is a residential Chicago skyscraper that was completed in 2019. It’s the tallest apartment building in Chicago. It has three stacked parts to resemble Willis Tower, but it’s structurally unique.

Rental units range from $2,195 to $13,900 a month. The building is close to Lake Michigan, so it’s within walking distance of many famous attractions, such as Millenium Park, the Art Institute of Chicago, and the Field Museum.

Frequently Asked Questions (FAQ)FAQ

How Many Skyscrapers are in Chicago?

There are 126 skyscrapers in Chicago, making it the city with the second-most skyscrapers in the US, after New York.

What’s the Oldest Skyscraper in Chicago?

Of the 86 tallest buildings in Chicago, the oldest is the Chicago Temple Building, built in 1924. It’s 568 feet tall with 23 floors, so it wouldn’t count as a skyscraper if it was built by today’s standards.

What is the Definition of a Skyscraper?

A skyscraper is a tall, habitable building with many floors. The original definition stated that it needed at least 10 to 20 stories, but modern skyscrapers must have 40 or more stories.

Which Chicago Skyscrapers Have Observation Decks?

There are two main observation decks in Chicago: 360 Chicago at 875 North Michigan Avenue and Skydeck at Willis Tower. Aon Center’s observation deck and thrill ride are coming soon, and you can also get great views from the Centennial Wheel at Navy Pier.

How Long Will Willis Tower Last?

When Willis Tower was built, it was believed that it would last 150 years. It may need to be demolished and replaced at that point, but it depends on what happens to the other Chicago buildings over the years.


Chicago’s tallest buildings are some of the biggest and most impressive towers in the US. They cover a wide variety of purposes, including tourist attractions, shops, restaurants, hotels, rentals, and offices.

Next time you’re exploring Chicago, don’t forget to look up and identify some of the skyscrapers of Chicago. They all have a unique history and structure.