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.
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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.
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.
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.
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.
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.
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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.”
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.
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.
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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.
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.
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.
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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.
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.
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.
Center, right of KEMPER building. Photo: Joaquin Ossorio Castillo/Shutterstock
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.
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.
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.
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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.
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.
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.
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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.
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.
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.
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.
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.
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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.
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.
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. 
