Chicago buildings overlooking the Chicago RIver
Elizabeth Bacharach

A Tour of 12 Architecture Icons in Chicago

Considered the birthplace of the skyscraper, downtown Chicago has long been a center of architectural innovation. After much of the city was destroyed in the Great Chicago Fire of 1871, the rebuilding process was undertaken with a spirit of experimentation and invention that remains intact today. Clustered along Lake Michigan and the Chicago River, the buildings in this midwestern metropolis include record holders, exemplars of design, and creations dreamed up by some of the biggest names in 20th- and 21st-century architecture. Let’s go on a virtual tour of our favorites.
Carbide and Carbon Building in Chicago, IL
Dave Taylor/Flickr
Carbide and Carbon Building
Where: 230 N. Michigan Avenue 
Looking at Chicago’s downtown skyline from a distance, it’s pretty easy to pick out the Carbide and Carbon Building—it’s the one that looks like a giant champagne bottle with gold foil at the top. Completed in 1929, the Art Deco building’s dark green granite façade reaches up to a cap ornamented in genuine 24-karat gold with bronze trim. This flashy design was originally devised for a company that made dry-cell batteries, but the current occupant, Chicago’s Hard Rock Hotel, seems more in keeping with the glitz of the edifice. 
35 East Wacker in Chicago, IL
Joseph Kranak/Flickr
35 East Wacker
Where: 35 E. Wacker Drive
Legend has it that Chicago’s most infamous gangster once held court at this 40-story neoclassical building. After completion in 1926, the building’s dome became home to the Stratosphere Lounge, a restaurant where none other than Al Capone supposedly ran a speakeasy. Back then the skyscraper was known as the Jewelers Building, thanks to the many diamond merchants based here, and its claims to fame included one of the country’s biggest indoor parking garages, where an elevator system could transport gem-toting jewelers safely to their offices without getting out of their cars. From the outside, the building stands out from its neighbors with a handsome dome and ornate terracotta ornamentation. 
333 West Wacker in Chicago, IL
Elizabeth Bacharach
333 West Wacker
Where: 333 W. Wacker Drive 
Chicago Mayor Rahm Emanuel has named this curving, glass-fronted modern building one of his favorites in the city. You might recognize it from Ferris Bueller’s Day Off, where it served as Mr. Bueller’s office building. Due to its rounded glassy surface and prime spot along the Chicago River, it reflects both the water and the city’s skyline, seeming to ripple along with the current as you go walking, driving, or boating past. 
Civic Opera Building in Chicago, IL
Civic Opera House
Where: 20 N. Wacker Drive 
With its 45-floor central tower and flanking 22-story wings, the Civic Opera House looks something like a giant chair plopped down into the Loop. As a matter of fact, it’s been called “Insull’s Throne” in reference to the guy who had it built—business magnate Samuel Insull. Completed in 1929 after only 22 months of construction, the limestone behemoth features a 3,563-seat opera house owned and operated by the renowned Lyric Opera of Chicago
Willis Tower in Chicago, IL
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Willis Tower
Where: 233 S. Wacker Drive 
For about 25 years after its completion in 1973, the structure that to some Chicagoans will forever be known as the Sears Tower was the tallest building in the world. That distinction now belongs to the Burj Khalifa in Dubai, while New York’s One World Trade Center holds the current record for height in North America. Still, the Willis Tower’s 110 stories are nothing to sneeze at—especially when you take a stomach-lurching step out onto the glass-enclosed ledge on the 103rd-floor observation deck
Merchandise Mart in Chicago, IL
Elizabeth Bacharach
Merchandise Mart
Where: 222 W. Merchandise Mart Plaza 
You’ll see some interesting ornamentation on the façade of this riverside commercial complex—lots of zigzags and diagonals reflecting the tastes of its ‘20s-era designers. But the most noteworthy feature of the Merchandise Mart is its size. Put simply, the place is big, covering two and a half city blocks and some 4 million square feet. Built by the department store owners Marshall Field & Company and later owned for decades by the Kennedy family (yes, that Kennedy family), the building is still occupied by retailers and wholesalers, with a special emphasis on interior design showrooms.
Marina City in Chicago, IL
Marina City
Where: 290 N. State Street 
You’ve likely seen these two corncob-shaped towers before, perhaps on the album cover of Wilco’s Yankee Hotel Foxtrot or in movies such as The Dark Knight. The pair of midcentury-modern concrete marvels—which house apartments, entertainment venues, and a perilous-looking parking garage—were designed by architect Bertrand Goldberg, who did his darnedest to include no right angles anywhere. Sharp angles don’t exist in nature, he reasoned, so why should they be in architecture? 
Wrigley Building in Chicago, IL
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Wrigley Building
Where: 400-410 N. Michigan Avenue 
Chewing gum magnate William Wrigley, Jr., wanted his Michigan Avenue office building to look like the floodlit White City built for Chicago’s famous World’s Columbian Exposition of 1893. To that end, the building bearing his name features six different shades of white terracotta that gets brighter in color toward the building’s summit. And, sure enough, the whole thing is illuminated from the outside every single night. Though the gum company no longer has offices in the building, the name can never be changed because of a stipulation made when it was sold.
Tribune Tower in Chicago, IL
Fabrice Florin/Flickr
Tribune Tower
Where: 435 N. Michigan Avenue
The neo-gothic Tribune Tower cuts an imposing figure along the Chicago River. Get closer, and you’ll find some intriguing details entirely appropriate for the headquarters of an international media company. Embedded in the façade at street level are fragments of stone and other materials taken from more than 120 famous spots around the world, including Yellowstone National Park, the Great Wall of China, and the Parthenon in Athens. The earliest fragments were brought back to Chicago by Tribune correspondents at the request of Robert R. “Colonel” McCormick, the paper’s legendary editor and owner from the 1920s to the mid-‘50s.
The Rookery Building in Chicago, IL
Luke H. Gordon/Flickr
The Rookery Building
Where: 209 S. LaSalle Steet
Completed in 1888, the 11-story Rookery is the oldest high-rise in Chicago still standing. When it opened, its metal framing, elevators, electrical lighting, and plate glass were all state of the art. More striking today, however, are features like the building’s glass ceiling, which creates an interior “light court," and a white marble lobby redesigned in 1907 by Frank Lloyd Wright—his only surviving creation in downtown Chicago. 
Sullivan Center in Chicago, IL
Jaysin Trevino/Flickr
Sullivan Center
Where: 1 S. State Street 
What makes this structure iconic is the intricate ironwork around and above the corner entrance. Floral and flowing, the lush ornamentation was designed by architect Louis Sullivan to attract customers to the department store—first Schlesinger & Mayer and then, for decades afterward, Carson, Pirie, Scott and Company—housed inside. Another ideal feature for a retail space: huge bay windows maximize the amount of daylight entering the interior to illuminate displays. In a testament to changing retail fortunes, the place is now a Target.
Aqua in Chicago, IL
Where: 225 N. Columbus Drive
Aqua, which was completed in 2009, holds the distinction of being the tallest building in the United States designed by a female-owned firm—Jeanne Gang’s Studio Gang Architects. The 87-story residential and hotel tower features dozens of rippling white concrete balconies varying in size and shape. Taken with the surface’s blue-tinted glass, the undulating balconies create the impression of water flowing down the tower’s sides, an image meant to remind viewers of where the story of Chicago always has to start: mighty Lake Michigan.