For decades, Chicago laws limited the height of its buildings — and, by extent, the imagination of its architects. In the 1920s, the city's tallest were the likes of the Tribune Tower and the clock tower Wrigley Building, both between 400 and 500 feet tall.
This cap fluctuated throughout the years, but in the 1950s, the restrictions changed. These changes paved the way for the new tallest buildings in Chicago.
As Chicago grew and changed, so did its skyline. Small communities peppered with single-family homes and simple shops gave way to large structures. These 12 beautiful skyscrapers — ordered by height — are where you want to go when you’re strolling around Chi-town, exploring all the things to do in Chicago.
1. Willis Tower (Formerly Sears Tower)
Take your Dramamine and put on your boots because you’re about to conquer the most daunting skyscraper in the Windy City. Willis Tower — formerly known as Sears Tower — is the tallest building in Chicago, measuring a gulp-inducing 1,450 feet high (1,730 feet high if you count the twin antenna towers, and why wouldn’t you?).
That’s 110 stories of office space and one record for being the 12th-tallest building in the world. Not bad for a famous skyscraper that didn’t even exist until 1973. Make sure you take the time to make your way to the Skydeck observation deck on Willis Tower’s 103rd floor. No worries — the entire elevator ride from the lobby to the Skydeck takes around 70 seconds. Your ears will pop, but that’s a small price to pay for stepping foot onto the highest viewing area in the United States.
On a clear day, you’ll be able to see around 40-50 miles into the distance. That should give you a glimpse of Indiana, Michigan, and Wisconsin.
The Willis Tower is king of unique architectural features. If you’re feeling especially spunky, you can edge your way onto The Ledge. It's a series of glass boxes that jut out about 4.3 feet beyond the end of the Skydeck itself. Three layers of thick glass stand between you and the ground 1,353 below — are you game?
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2. Trump International Hotel & Tower
Located on the waterfront, Trump International Hotel & Tower is a memorable piece of modern architecture in the city’s skyline. Ninety-two stories, 5-star service that’ll make you feel like a visiting dignitary, and a 23,000-square-foot spa are a few things to expect.
But long before Trump filled his tower with luxury guest rooms and hotel condo suites, the building was the brainchild of Adrian Smith. When Trump Tower was conceived, it was to take over as the tallest building in the world. But the events of 9/11 scaled back those plans.
In spite of the changes, the skyscraper still took up significant real estate across the architectural landscape of Chicago when it opened in 2009.
The skyscraper holds court over prime real estate right up against the Chicago River and the Chicago Riverwalk, a bustling space brimming with eateries, parks, and even places where you can rent a boat or kayak.
Although this tower is one of the tallest skyscrapers in 2023, the planned Tribune East Tower is set to overtake it.
3. St. Regis Chicago
St. Regis Chicago may be one of the newest kids on the block, but the tower’s imposing 101-story, 1,198-foot frame is anything but quiet or timid. Construction on St. Regis kicked off in 2016 and finished in 2019. At its completion, it became the third-tallest in Chicago and the tallest female-designed structure on the planet. Kudos to architect Jeanne Gang.
Three cheers for Ms. Gang’s ingenuity, too, because the St. Regis is an absolute marvel. It's composed of three interconnected towers that seem to undulate right in front of your very eyes.
It’s a brilliant creation, and together with windows covered in alternating shades of glass, the hotel and condo-filled building has completely altered the look of the Chicago skyline and provided onlookers with futuristic eye candy.
4. Aon Center
Sometimes a big brand wants to make a big statement, and that requires a big headquarters. That’s exactly what happened when the Standard Oil Company of Indiana wanted a new home base in Chicago. Edward Durell Stone, the man behind D.C.’s Kennedy Center, got the job, and the then-named Standard Oil building became the second-tallest in Chicago.
During decades over Chicago’s Loop, the Standard Oil building has changed its name and gotten facelifts several times. Its ranking has lowered, though, and it’s now only the fourth-tallest building in the city.
Although the height of the modern-day Aon Center is still the original 83 floors and 1,136 feet, it’s changed. It turns out the 43,000 slabs of Italian Carrara marble used to cover the building in the ‘70s cracked under the pressure of chilly Chicago winters. In the early 1990s, granite replaced the marble.
5. 875 North Michigan Avenue (Formerly John Hancock Center)
We’ve talked about the tallest buildings in Chicago, but which skyscraper has the best view? The John Hancock Center — given the less stately name of 875 N. Michigan Avenue in 2018 — is where you’ll find 360 Chicago Tilt.
You can take advantage of the Tilt’s unique design that allows you to slant, face-down, over the city from 1,030 feet up in the air. Need liquid courage? That’s served up at the CloudBar, where you can grab a martini or margarita while you catch your breath from gazing down at the Magnificent Mile.
It’s an attraction that probably seemed inconceivable to developer Jerry Wolman when he conceived and owned the building (with backing from the John Hancock Mutual Life Insurance Company) in the mid-to-late 1960s. Engineering issues and bankruptcy pushed Wolman out of the picture.
Half a century later, companies rule over the skyscraper’s 100 floors and 1,127 feet of shops, restaurants, and residential amenities. Locals know 875 North Michigan Avenue for the band of white lights at the top that shift color to recognize Christmas and sporting events.
6. The Franklin Center
Locals refer to The Franklin Center simply as “The Franklin”, a level of casual familiarity that makes sense given the building has been snuggling into the Chicago skyline since the late 1980s.
Coming in at a respectable 60 stories and 1,007 feet high, The Franklin is a mainstay in the Loop, sitting just a couple of blocks from the Chicago River and featuring architectural setbacks that allow sunlight to filter around the granite-clad building.
What was once a single building became a two-for-one deal when the then-named AT&T Corporate Center joined the USG Building next door. There’s a 16-story atrium linking the two independent spaces, creating a functional and mesmerizing marriage of space, design, and history.
One of the more interesting aspects of The Franklin is its coloring. Deep, rich red at the bottom, the skyscraper’s exterior sweeps to a light rosy beige near the tip, softening the other gothic detailing. In other words, it might not be the biggest tower in the city, but it could be the one most worth gawking at.
7. Two Prudential Plaza
As another member of the Loop’s skyscraper posse, Two Prudential Plaza holds court as the 28th-tallest building in the United States, thanks to its 64-story height.
It’s relatively new, with construction completed in 1990, and it’s easy to spot due to a series of art deco-esque chevron setbacks that are stacked on top of each other to create a pyramid sharply tapered peak 995 feet into the air.
The building is one half of a sibling duo, joined by its sister property One Prudential Plaza. They create the quirkily tagged One Two Pru, which is filled with high-end office spaces and luxe amenities. Tenancy is so coveted that One Two Pru has housed the Consulate General of Canada in Chicago, several key area AM and FM radio stations, and even the Chicago Tribune.
8. One Chicago
One Chicago, formerly known as One Chicago Square, is the 8th-tallest building in Chicago and the 35th-tallest in the United States. It’s also a relative newbie, with construction initiated in 2019 and the tower topped out in 2021.
The two-tower extravaganza opened for business as a mixed-use development that holds some 800 residences, as well as retail establishments, office spaces, a gym, and an event center.
As much as One Chicago changed the landscape of the city’s skyline, it also altered the look and feel of the area around the buildings. The main tower is about 45 feet back from the road, making way for an urban park that acts as a peaceful oasis amid the hubbub of urban chaos.
The second tower is closer to the road but has its own commendable architectural intricacies, including a cascade of roof terraces, a podium that juts out over the building’s pool decks, and a truck turntable on the ground floor to ease parking and make coming home a mind-blowing experience.
9. 311 South Wacker Drive
Completed in 1990, 311 South Wacker Drive was once the tallest reinforced concrete building in the world. That title now belongs to the altitudinous Burj Khalifa in Dubai, but 311 South Wacker Drive still has a lot going for it.
The skyscraper is best known for its unique crown that includes five cylinders. Four smaller peg-like structures surround a 105-foot central cylinder. They're all lit by 1,852 fluorescent tubes that create a shining array of light known for shifting colors to honor holidays and special events.
Tenants in the trophy tower enjoy 360-degree views of local attractions like Grant Park, the Chicago River, and Lake Michigan. The five-story Wintergarden lobby is an undisputed masterpiece.
It was intended to serve as a commuter link, giving new life to an existing but disused streetcar tunnel running nearby. However, the glass-ceilinged marvel has been more aesthetically minded and has contained a fountain, palm trees, and Raymond Kaskey’s breathtaking creation, Gem of the Lakes.
The building also abuts the largest green area in the Loop. There, Chicagoans can grab tomatoes from the farmers market, take in a concert, and celebrate art and culture at one of the city’s festivals. And for those who enjoy greenery but crave a rugged nature experience, the surrounding areas offer trails for hiking near Chicago, perfect for a day trip outside the urban landscape.
10. NEMA Chicago
The 896-foot-tall NEMA isn’t the tallest building in Chicago. It is the tallest all-rental residential building in the city, with 800 apartments spread over 76 floors. It’s fascinating. Three stacked parts come together to create a sculpture-like skyscraper that pays homage to the Willis Tower.
The middle section is the star, with cutaways that turn the central chunk of the NEMA into a steel and concrete staircase. The upper section is indented, but those angles leave plenty of room for 70,000 square feet of amenities. These include coworking spaces, an indoor/outdoor swimming pool, basketball and squash courts, a kids' room, and a ballroom.
NEMA is brimming with smart home technology, such as touchless building entry and apartment access. It’s made an impact on not only Chicago’s skyline but also on city living in general.
11. 900 North Michigan
Holding court over the much-ballyhooed Magnificent Mile sits 900 North Michigan, a building that embodies the best parts of luxury living and urban shopping. The 871-foot-tall building is the 11th-tallest skyscraper in Chicago.
It stands out even more as a result of its limestone- and green glass-clad exterior. The materials are reflective, adding to the luminescence created by four color-changing lanterns built into the top of the structure.
One of the building’s major draws is a green roof created by Hoerr Schaudt. What was once a barren 10th-floor rooftop adorned with little more than an abandoned running track, weeds, and debris has been transformed into a multipurpose expanse where tenants can admire the lush greenery, host a cookout, or simply gaze out over the city.
900 North Michigan shops occupy much of the skyscraper’s rear, six-story atrium, with some shops scoring prized Michigan Avenue frontage and others clustered around zigzagging escalators. This plus other amenities help make the building a notable part of Chicago’s premier commercial district.
12. Aqua Tower
Remember architect Jeanne Gang’s stunning work on St. Regis Chicago, also known as the Wanda Vista Tower? Gang also led the team behind Aqua Tower, an 80-story, 859-foot-tall wonder once named skyscraper of the year. Built on a former rail yard, Aqua is the best kind of architectural oddity, marked by irregular ripples of white concrete balconies that jut out from the building by up to 12 feet.
With these perches, residents have an opportunity to see beyond the skyscraper’s facade and take in the best parts of Chicago. It’s a cliff face-like arrangement Gang says was inspired by actual topographical features found around the Great Lakes.
The terrace extensions also maximize solar shading, a benefit that’s perfectly aligned with Gang’s mission to prioritize sustainability. Energy-efficient lighting and water-efficient irrigation are just two of the efforts that helped the tower become LEED-NC certified.
It’s these accomplishments that helped not only to cement Gang’s status as an architectural ace but also to put the Lakeshore East neighborhood on the map as a stellar place to live, work, and play.
Explore the Soaring Modern Skyscrapers of Chicago
The Chicago skyline has shifted dramatically over the last century or so, as has the slate of entertainment on tap for the city’s denizens and adventure-seeking visitors. Whether you’re tilting toward the Windy City’s treasures atop the skyscraper formerly known as the John Hancock Center, or booked into a room at the NEMA, you can become a part of the city’s history.
And for an evening of spectacular performances, the live shows in Chicago are a testament to the city's vibrant cultural scene.
As you build your skyscraper-hopping itinerary, don’t forget to include a few moments to be amazed in other ways. Our shows in Chicago perfectly merge imagination and innovation, delivering creative knockouts as iconic as the buildings that make up this sensational Midwestern city. Book tickets today, and make your time in Chicago an adventure to remember.