Chicago’s skyline has not always been filled with gleaming skyscrapers. The Great Chicago Fire in 1873 wiped out most of the city, displacing one-third of its residents. Though a tragedy, the fire led to improved building materials and fire codes, which paved the way for the age of the skyscraper.
The skyline you see today is an amalgamation of more than a century of various architectural styles, building materials, attainable heights, and sustainability efforts.
Impressive from any angle, the Chicago skyline is best viewed from Lake Michigan. Take an architectural river cruise on the Chicago First Lady or Wendella boat an hour before sunset to witness the sky turn pink and orange behind the skyline from the lake and watch the city transform from day to night as you head back on the Chicago River.
If a boat cruise isn’t your thing, head to the Museum Campus for a slightly less panoramic view along the shoreline between the Shedd Aquarium and the Adler Planetarium. Or you can go to one of Chicago’s two public observation decks for 360-degree views stretching more than 50 miles.
Regardless of your location for observing the Chicago skyline, you’ll want to familiarize yourself with the most prominent buildings. It’ll help you plan your Windy City adventure and impress your friends with your in-depth knowledge of the historic city.
1. 311 South Wacker Drive
- Address: 311 S. Wacker Dr.
- Floors: 65
- Height: 961 feet
- Fun fact: At one time, it was the tallest reinforced concrete building in the world
When you see the Chicago skyline from Lake Michigan – hands-down the best vantage point for viewing it – the first prominent building on the left is 311 South Wacker Drive. This skyscraper is known for its illuminated and distinctive crown: a 105-foot-tall, translucent cylinder surrounded by four smaller cylinders. The crown’s color changes to mark holidays and local celebrations.
While there’s no observation deck at the top, there’s plenty to do at ground level. The five-story lobby has an impressive fountain, as well as a glass-ceilinged atrium. On the northwest side of the building is a one-acre park – the largest open green space in the Chicago Loop. It hosts everything from farmers’ markets to cultural festivals to concerts throughout the year.
2. Willis Tower
- Address: 233 S. Wacker Dr.
- Floors: 103
- Height: 1,450 feet
- Also known as: Sears Tower
- Fun fact:The tower’s average sway is about six inches, but it’s designed to sway up to three feet
In as quickly as 60 seconds, you can go from sea level to 1,400 feet in the air to visit the top of Chicago. The Skydeck on the 103rd floor of Willis Tower offers impressive views of the Chicago skyline and visitors can see up to 50 miles. On clear days, you can see four different states, but the best time to go is an hour before sunset. That’s when you’ll witness the city’s colorful transformation from day to night.
While enjoying the views, take it one step further – literally – on the Ledge. The glass-bottomed platform, raised 1,353 in the air, offers a chance to walk over the city, looking down onto Wacker Drive and the Chicago River below.
3. Chicago Board of Trade
- Address: 141 W. Jackson Blvd.
- Floors: 44
- Height: 604 feet
- Fun fact: A statue of Ceres, the Roman goddess of agriculture, sits atop the building.
If you plan to visit Chicago’s financial district, check out the Chicago Board of Trade (CBT) building at the head of the LaSalle Street Canyon. Inside, grab a bite to eat at the Ceres Café while you appreciate the lobby’s marble, three-story walls lined with elaborate murals.
You’ll need to take a tour to explore beyond the lobby. The Chicago Architecture Foundation offers an art-deco tour of buildings in the Loop that includes the CBT, and the Chicago Merc (CME) offers tours of the trading floors.
Outside, you can recreate scenes from your favorite movies as the building’s façade is a favorite among filmmakers. The streetscape was a backdrop in movies like Man of Steel, Road to Perdition, Transformers: Dark of the Moon, and The Untouchables. You may recognize the CBT from the memorial scene in Batman: The Dark Knight, where the Joker makes his attempt on the life of Gotham City’s mayor.
4. 111 South Wacker Drive
- Address: 111 S. Wacker Dr.
- Floors: 51
- Height: 681 feet
- Fun fact: This building is LEED-certified on multiple levels and was the largest LEED-platinum-certified building in the US when it earned the award in 2019
This relatively new (2005) office building is recognizable in the Chicago skyline by its panes of blue glass. The first seven floors of the skyscraper house a dramatically lit spiraling ramp that reflects down into the 44-foot tall lobby below. The spiral theme continues through the lobby and onto the pavement outside. It’s closed to the public but worth admiring from the outside if you’re into sustainable architecture.
5. Franklin Center
- Address: 227 W. Monroe St.
- Floors: 60
- Height: 1,007 feet
- Also known as: The Franklin, formerly the AT&T Corporate Center
- Fun fact: The Franklin has rotating featured artists on display open to the public midweek
Beyond the elaborate lighting fixtures and lobby’s marble floors and walls, there’s not much for the public to see here. The building contains retail and office spaces. In the Chicago skyline, it stands out thanks to its gigantic presence, spiked roof pinnacles, and illuminated setbacks on the exterior.
6. Kluczynski Federal Center
- Address: 230 S. Dearborn St.
- Floors: 42
- Height: 562 feet
- Fun fact: This modern design is from the famed architect (also called star-chitect) Ludwig Mies van der Rohe
Named after a former congressman, the Kluczynski Federal Center was designed without the usual lavishness found in civic buildings, but the Federal Center Plaza outside is worth a visit. This public square hosts farmers’ markets, festivals, and protests. It’s also home to the famed public art sculpture “The Flamingo.”
7. 333 South Wabash
- Address: 1333 S. Wabash Ave.
- Floors: 44
- Height: 600 feet
- Also known as: Big Red, CNA Tower
- Fun fact: It’s one of Chicago’s most recognizable office buildings, for the obvious reason
Painted bright red, 333 South Wabash stands out on the Chicago skyline day or night. The windows are often used to display lighted messages for holidays and local celebrations. There used to be a popular dining hall inside, but it closed in early 2022.
8. Metropolitan Tower
- Address: 310 S. Michigan Ave.
- Floors: 30
- Height: 475 feet
- Also known as: The Beehive Building, formerly the Straus Building
- Fun fact: It was the first building in Chicago with 30 or more floors
If you pose with the famous lion statues guarding the Art Institute of Chicago, you’ll glimpse the Metropolitan Tower up-close. The U-shaped condo complex sits on Michigan Avenue facing Grant Park.
The Metropolitan Tower stands out in the Chicago skyline at night thanks to a 40-foot pyramid on the roof, adorned with a 20-foot glass “beehive” ornament that emits a bright blue light.
9. Chase Tower
- Address: 10 S. Dearborn St.
- Floors: 60
- Height: 850 feet
- Fun fact: There’s a mosaic by Marc Chagall in the outdoor plaza
If you’re in the Loop, head to Chase Tower. If you’re nearby, stand close and look up for a unique view of the distinctive curved shape; it’s hard to appreciate looking at the Chicago skyline from afar.
The building and adjacent plaza cover an entire city block. Inside is the Chase Auditorium, the long-time home for NPR’s news quiz show Wait Wait… Don’t Tell Me! In front is the Exelon Plaza, a sunken space that marks the geographic center of the Loop.
10. 55 East Monroe
- Address: 55 E. Monroe St.
- Floors: 49
- Height: 583 feet
- Also known as: Mid-Continental Plaza
- Fun fact: This building was originally planned to be two 40-story towers
This is an office building with 10 floors of condos at the top. It’s also the home of what’s currently Forum 55 Food Hall, though be sure to check the hours before you go as they’ve opened and closed several times since the start of the COVID-19 pandemic.
11. The Legacy at Millennium Park
- Address: 60 E. Monroe St.
- Floors: 72
- Height: 5822 feet
- Also known as: Legacy Tower
- Fun fact: The building’s narrow design ensures great views for all residents
This tall, blue-glass member of the Chicago skyline is a condo building and has classroom space for the School of the Art Institute of Chicago. Besides admiring from afar, there’s nothing for the public to do.
12. Richard J. Daley Center
- Address: 50 W. Washington St.
- Floors: 31
- Height: 648 feet
- Also known as: Chicago Civic Center
- Fun fact: It’s the tallest flat-roofed building in the world with fewer than 40 stories (thanks to the high ceilings needed for courtrooms)
While the Richard J. Daley Center building is interesting from an architectural point of view, the real draw is the Daley Center Plaza, which houses fountains and a 3D, 50-foot-tall cubist sculpture by Pablo Picasso. Often referred to as “The Picasso” or “The Chicago Picasso,” the sculpture is officially unnamed and makes for a fun photo op.
Every weekday at noon, the plaza offers a Noontime Event, which features free cultural programming at the Picasso.
13. Grant Thorton Tower
- Address: 171 N. Clark St.
- Floors: 50
- Height: 756 feet
- Also known as: Chicago Title and Trust Center
- Fun fact: It won the Chicago Athenaeum’s “Best Building” Architecture Award in 1990
Located on the former site of Chicago’s Greyhound Bus Station, the Grant Thornton Tower is a skyscraper known for its unique roof. The east side of the roof features a steep slant, while the west side looks like something topping a Mayan temple. Both sides are illuminated brightly at night, making the tower stand out in the Chicago skyline.
14. 77 W. Wacker
- Address: 77 W. Wacker Dr.
- Floors: 50
- Height: 668 feet
- Also known as: R.R. Donnelley Building, United Building
- Fun fact: The building has rooftop inspired by ancient Greece
Fans of the film The Negotiator will recognize 77 West Wacker as the offices for the movie’s Internal Affairs Division of the Chicago PD. In real life, it’s a post-modern office building on the Chicago River.
The ground floor has a 59-foot tall atrium – a fairly modern concept – but the roof has triangular gables akin to those you’d find on ancient Greek buildings.
Directly next to this building, but hard to see, is the Pittsfield Building, with 38 floors and a height of 557 feet. The building is named for the town in Massachusetts where department store founder Marshall Field first worked. It was built in the 1920s and stands out in the Chicago skyline with its traditional setbacks and green pyramid-shaped roof. Inside is a five-story shopping area lined with balconies and stores. Be sure to come hungry, as the Pittsfield Café is known for delicious skillet meals and bloody Marys.
15. 35 West Wacker
- Address: 35 W. Wacker Dr.
- Floors: 50
- Height: 635 feet
- Also known as: The Leo Burnett Building
- Fun fact: Square windows show off one version of the “Chicago windows” common to the Chicago Style of architecture
Remember the Discovery Channel special feature where professional daredevil Nik Wellenda successfully crossed the Chicago River on a high wire? He began at the west Marina Tower and ended at 35 West Wacker (then known as the Leo Burnett Building).
The general public can visit Catch 35, the upscale seafood restaurant on the first floor of 35 West Wacker. In addition to delicious cuisine, the Catch 35 has live jazz music Tuesday through Sunday evenings.
16. The Heritage at Millennium Park
- Address: 130 N. Garland Ct.
- Floors: 57
- Height: 631 feet
- Fun fact: It’s the tallest purely residential building in the Loop
Designed by the same firm as Legacy Tower, The Heritage is on the west side of Millennium Park. It has a rooftop terrace with gorgeous views of the Chicago skyline, lake and parks, as well as the bi-weekly summer fireworks. Unfortunately, the terrace is not open to the public.
17. Crain Communications Building
- Address: 150 N. Michigan Ave
- Floors: 41
- Height: 582 feet
- Fun fact: This building was featured in the 1980s classic Adventures in Babysitting
Owing to its diamond-shaped flat top with a vertical gap down the center, the Crain Communications Building is known to most Chicagoans as the Diamond Building – or, to some, the Vagina Building. Urban legend claims the building was designed to combat the typical phallic shape of skyscrapers, but the man who designed the building claims it’s a coincidence. Regardless of what you call it, you’ll have great views of it from Maggie Daley Park or Millennium Park.
The diamond-shaped-roof is outlined in white lights and often displays illuminated messages to celebrate sporting events and holidays.
18. AMA Plaza
- Address: 330 N. Wabash Ave.
- Floors: 52
- Height: 695 feet
- Fun fact: This building was featured in the first episode of Ozark, as well as Batman: The Dark Knight
Located on the Chicago River, the AMA Plaza is home to the Langham, a high-end hotel with two restaurants you won’t want to miss. Travelle serves upscale American seasonal breakfast, lunch, and dinner, while Pavillion hosts the popular Langham Afternoon Tea, starting at noon on weekends.
19. Trump International Hotel & Tower
- Address: 401 N Wabash Ave.
- Floors: 98
- Height: 1,388 feet
- Also known as: Trump Tower
- Fun fact: Originally planned to be the world’s tallest building, it was scaled down after the September 11th attacks
Built on the site of the former Chicago Sun-Times building, Trump Tower is on the north bank of the Chicago River next to the iconic Marina Towers (shaped like corn cobs). The tower hosts a hotel and condominiums, as well as great views of the buildings lining the Chicago River.
Trump Tower was designed to fit in with and visually complement the surrounding buildings. It has a unique, asymmetrical shape and sticks out on the Chicago skyline thanks to its flat roof and off-centered spire. And yes, there are significant efforts underway to rename the building.
20. Two Prudential Plaza
- Address: 180 N. Stetson Ave.
- Floors: 58
- Height: 995 feet
- Fun fact: The building and its plaza make a cameo in the 1994 movie Richie Rich
As the sister skyscraper of One Prudential Plaza, Two stands out in the Chicago skyline thanks to its chevron-shaped setbacks and an 80-foot spire set on top of a 45-degree rotated pyramid.
21. Aon Center
- Address: 200 E. Randolph St.
- Floors: 83
- Height: 1,136 feet
- Also known as: Standard Oil Building, Amoco Building
- Fun fact: The building was completely refaced at a cost of $80 million after Chicago’s massive temperature swings caused a chunk of marble to fall off the building
Plans are underway to create an observatory and restaurant atop the Aon Center, accessible to the public via an external glass elevator projected to be the fastest in the country. The observatory will feature a ride called Sky Summit, which will take riders over the edge of the roof for a unique view of the Chicago skyline.
Aon Center also has plans to create a family-friendly entertainment center on its lower levels.
22. Blue Cross Blue Shield Tower
- Address: 300 E. Randolph St.
- Floors: 54
- Height: 744 feet
- Fun fact: This building was constructed in two different phases across two decades
When the Blue Cross Blue Shield Tower was originally constructed, the owners intended to expand it upward. More than a decade later, builders added another 24 floors. The tower frequently acts as a Chicago skyline message board on the side facing Grant Park, addressing healthcare issues and cheering on local sports teams.
23: 340 on the Park
- Address: 340 E. Randolph St.
- Floors: 62
- Height: 672 feet
- Fun fact: 340 on the Park briefly held the title of “tallest all-residential building in Chicago”
If you’re near Millennium Park and have a taste for seafood, check out Brown Bag Seafood Co. inside 340 on the Park. The restaurant aims to “bring seafood to the masses” (meaning it has reasonable prices), and the skyscraper itself is one of the most eco-friendly in the Chicago skyline.
24. Park Tower
- Address: 800 N. Michigan Ave.
- Floors: 70
- Height: 844 feet
- Fun fact: It’s one of the tallest non-steel structures in the world
Park Hyatt Hotel makes up the lower portion of Park Tower, while the upper floors house condominiums. Within the hotel is a fantastic restaurant – NoMI, a nod to its “North Michigan” Avenue location.
The restaurant has three parts. “The Kitchen” offers upscale American cuisine and “The Lounge” is a sushi bar, wine cellar, and spacious bar. “The Garden” is an open-air terrace. If you’re looking for views of Chicago’s historic water tower, Lake Michigan, or the Chicago skyline, it’s the perfect place to enjoy a bite to eat.
25. 900 Michigan
- Address: 900 N. Michigan Ave.
- Floors: 766
- Height: 871 feet
- Fun fact: 900 Michigan hosts everything from art installations to cooking classes and musical performances in the mall area throughout the year
900 N. Michigan lights up the Chicago skyline with four rooftop lanterns that stand out at night along the Magnificent Mile. Inside the building is a Four Seasons Hotel and the 900 North Michigan Shops (a large, upscale shopping mall).
The mall has a six-story atrium with luxury retailers, restaurants, and a TopGolf Swing Suite where you can do everything from working on your swing to playing zombie dodgeball.
26. Park Tower
- Address: 875 N. Michigan Ave.
- Floors: 100
- Height: 1,128 feet
- Fun fact: Park tower pioneered the use of x-bracing — using crossed, X-shaped bars to resist movement from wind
875 North Michigan Avenue, widely still referred to as the John Hancock Building, is home to one of Chicago’s two observation decks. 360 CHICAGO offers views of the Chicago skyline, Lake Michigan, and up to three states from its position on the 94th floor. The ride to the top takes less than one minute.
360 CHICAGO has an enclosed platform, called TILT, that leans riders out over Michigan Avenue from 1,000 feet above street level. You can also grab a drink at Bar 94, Chicago’s highest bar.
27. Water Tower Plaza
- Address: 835 N. Michigan Ave.
- Floors: 74
- Height: 859 feet
- Fun fact: It’s named after the nearby Chicago water tower, which is one of the few buildings to survive the Great Chicago Fire of 1871
Water Tower Place is a vertical shopping mall with eight retail floors on the iconic Magnificent Mile on Michigan Avenue – an area known for shopping. The skyscraper also houses a Ritz-Carlton Hotel and condominiums.
Water Tower Place is an important part of the Chicago skyline because it opened the Magnificent Mile to middle-income shoppers by bringing economically mainstream stores into an area long dominated by upscale luxury brands.
28. Lake Point Tower
- Address: 505 N. Lake Shore Dr.
- Floors: 70
- Height: 645 feet
- Also known as: Lake Point Tower Condominium
- Fun fact: It’s the only skyscraper east of Lake Shore Drive
Lake Point Tower is well known for its tinted glass framed in gold metal that reflects sunlight off Lake Michigan, giving the building a golden glow. Its curved shape is said to have inspired the Chicago-born designer of Dubai’s Burj Khalifa, the tallest tower in the world.
Lake Point Tower has an upscale restaurant on its top floor, Cité, which features unbeatable 360-degree views from its sky lounge. It’s the perfect place to watch the sunset behind the Chicago skyline and witness the city come alive after dark.