Chicago’s skyline reflects diverse architectural design, resourcefulness, and innovation. Most of the buildings downtown were destroyed in the Great Chicago Fire of 1871—a notable exception being the still-standing Water Tower—which then set off a construction race to rebuild the city using the world’s best architects. Chicago quickly became the birthplace of the skyscraper with the completion of the Home Insurance Building in 1885. Today, the three tallest buildings in Chicago are the Willis Tower (known as the Sears Tower if you’re a Chicagoan), Trump International Hotel and Tower, and the Aon Center.
In addition to skyscrapers, Chicago is world renowned for its bungalows, graystones, and cathedrals. The city's museums are quite stunning, and everyone can agree that Wrigley Field, home to the Chicago Cubs and built in 1914, should be included on the list of notable architecture.
One of the best, and most fun, ways to learn about some of the Windy City’s famous architecture is on a boat tour with Chicago Architecture Center (or one of Chicago's other amazing on-water tours) where you can get a duck’s view of prominent buildings along the Chicago River. On a cruise, you’ll learn about shifts in design from load-bearing to skeleton frame construction, you’ll get a snippet of Chicago’s gangster history, and you’ll be able to see how the Chicago Civic Opera building looks like a colossal chair with protruding arms. Of course, you can also take a walking tour—Chicago is compact and easy to get around on foot.
Carbide & Carbon Building
This sleek, polished black granite and green terra cotta tower, with a gold and bronze-tipped spire, looks like a corked bottle of champagne. Designed by the Burnham Brothers in 1929, the Carbide & Carbon Building is a stunning example of Art Deco architecture. Stretching 37 stories high and set on Michigan Avenue, this building was designated a Chicago landmark in 1996. In the early 2000s, the building was transformed into the Hard Rock Hotel Chicago and in 2018, the building changed hands once again to the St. Jane Hotel.
The Rookery is an iconic building, positioned in heart of downtown Chicago's financial district. The building, a mashup of modern building techniques (elevators and fireproofing) and traditional design (ornamental brick facades), was completed in 1888 by Burnham and Root. In 1905, Frank Lloyd Wright remodeled the lobby with white marble and Persian-style ornamentation. The most stunning feature of The Rookery is the two-story light court, which provides natural light from above, illuminating the entire atrium.
311 South Wacker
This octagonal, pink skyscraper, with an illuminated white top ringed with glass cylinders, is said to resemble a diamond engagement ring. This building, built by Kohn Pedersen Fox Associates in 1990, stands out in the night sky because of the lighted tip, which changes colors for holidays and special occasions. The first-floor, multi-hued atrium has an impressive fountain, beautiful marble and lots of plants—it’s easy to see why they named this interior space Winter Garden.
875 North Michigan
875 North Michigan, previously known as the John Hancock Center, was built by Skidmore, Owings & Merrill. The tapered design of the building, with huge X-bracing on the exterior, makes this building stand out from the pack. Tourists flock to this building to visit the 360 CHICAGO observation deck, which offers panoramic views of the city and Lake Michigan. Thrill-seekers love TILT, a moving platform that tips you over Michigan Avenue from the 94th-floor. One level up, sits the award-winning Signature Room at the 95th, offering upscale American cuisine.
Of course, you can’t mention top buildings in Chicago without including the Willis Tower, formerly known as the Sears Tower. This 1,450-foot tower was completed in 1973, designed by the powerhouse architectural firm Skidmore, Owings & Merrill. Willis Tower was the tallest building in the world until 1988—now it’s the 12th tallest. Skydeck Chicago, an observation deck on the 103rd floor, is a popular tourist attraction, drawing 1.7 million visitors annually. Intrepid travelers can experience The Ledge, four glass cubes that extend over 4 feet outside of the tower.
The Aqua Tower, the tallest building created by a woman-led firm, stands out for its unique wavy water-like facade. These white concrete balconies, which are all unique in size and shape, transform the building into a work-of-art. Aqua, designed by Jeanne Gang of Studio Gang Architects, is an 82-story mixed use building with an enormous terrace on top, complete with gardens, gazebos, pools, hot tubs, and a running track.
One of the most beautiful buildings in Chicago, and a Chicago Landmark, is the Tribune Tower, a neo-Gothic skyscraper completed in 1925. The Chicago Tribune, Tribune Media, and Tribune Publishing have all called this building home and WGN Radio broadcasted from the building until 2018. If you walk along the building’s outside walls you can see pieces of world famous constructions and landmarks (like the Taj Mahal, Great Wall of China, and the Great Pyramids) embedded in the exterior.
The Wrigley Building
Another iconic building worth a look-see is Chicago’s Wrigley Building, located on the Magnificent Mile across from the Tribune Tower. This building, designed by architects Graham, Anderson, Probst & White for the Wrigley Company (the chewing gum giant), was Chicago’s very first air-conditioned office building. Built in the 1920s, the two-tower complex, connected by an elevated pedestrian bridge, lights up the night sky with its white exterior.
This corn cob-like set of concrete buildings, where you can see parked cars in the multi-story garage, was designed by Bertrand Goldberg and finished in 1968. Situated right along the Chicago River, the interior of this building has rounded hallways and pie shaped rooms. The original design was to create an accessible city within a city, with plenty of amenities and features.
theMART, formerly known as The Merchandise Mart, is a major hub for art, culture, and design. This massive, 25-story Art Deco building, covering 4 million square feet and spanning two city blocks, serves as a home for architects, designers, contractors, and technology companies like Yelp, PayPal, Conagra, Allstate, and more. theMART is so colossal, it has its own zip code. The city hosts Art on the Mart, colorful multimedia image art display showcased on the building’s facade.