Chicago does not hide its architecture. The buildings here are too tall, too loud, too certain of themselves to slip into the background. In most cities, you have to hunt for the good stuff. In Chicago, you have to look up, and you cannot avoid it.
The skyscraper was invented here. Not New York. Not Dubai. Chicago. After the Great Fire of 1871 burned down 17,500 structures and left a third of the population homeless, the city rebuilt with a ferocity that invented modern vertical construction. The Home Insurance Building, erected in 1885 at the corner of LaSalle and Adams, was the first to use a steel frame instead of load-bearing masonry. It stood ten stories. It was demolished in 1931. But the idea survived, and Chicago has been testing the limits of that idea ever since.
Start at the Chicago Architecture Center at 111 East Wacker Drive. Admission is $14, and the Chicago City Model Experience alone is worth it. A 1:50 scale diorama of the entire city, more than 4,200 buildings rendered in 3D-printed detail. The Willis Tower rises three feet from the baseboard. Every seven minutes, a light show burns the whole thing down to simulate the 1871 fire, then rebuilds it. It is theatrical, but it works. The center also runs the best architecture river cruise in the city aboard Chicago's First Lady, departing from 465 North McClurg Court. The 90-minute cruise costs $48 for adults, $30 for youth, free for kids under six. Volunteer docents from the CAC narrate. They know the difference between a spandrel and a pier, and they will tell you why the corncob-shaped towers of Marina City matter. Book a few days ahead in summer. The cruises run April through November, with daily departures from 10 a.m. to 8 p.m. In winter, the CAC switches to walking tours, mostly $30, covering the Loop, the Loop interior lobbies, and neighborhoods from Hyde Park to Bronzeville.
The river cruise is the fastest education you can get. From the water, you see the layers. The 1920s neo-Gothic Tribune Tower, its walls embedded with fragments from the Colosseum, the Great Pyramid, and the Berlin Wall. The white terra-cotta Wrigley Building, built by the chewing-gum fortune in 1924, its clock faces lit at night like a beacon for the north side. The twin corncobs of Marina City, Bertrand Goldberg's 1964 experiment in urban vertical living, where the parking garages occupy the first nineteen floors and residents live above them in pie-slice apartments. The Aqua Tower by Jeanne Gang, completed in 2010, its undulating concrete balconies rippling like water frozen mid-splash. It was the tallest building in the world designed by a woman at the time of completion. The St. Regis Chicago, also by Gang, a trio of interconnected crystalline towers completed in 2020, stands across the river at 363 East Wacker. It looks like three shards of obsidian leaning on each other for support.
Get off the boat and walk the Loop. The Rookery at 209 South LaSalle Street has a lobby redesigned by Frank Lloyd Wright in 1905. He stripped out the original Victorian ironwork and installed a white marble atrium with Persian-inspired geometric ornament and a central staircase that seems to float. It is free to enter during business hours. Wright was 24 years old when he worked on it. He was still an employee of Louis Sullivan at the time. The building itself was designed by Burnham and Root in 1888. Its exterior is a dark Romanesque fortress of brownstone and granite. The interior is Wright's first major independent statement.
Sullivan's own work is nearby. The Carson, Pirie, Scott and Company Building at 1 South State Street, now the Sullivan Center, was completed in 1899. The cast-iron ornament around the ground-floor windows is unmistakably Sullivan, all curling seed pods and geometric flora. He called it "organic ornament," and it was his answer to the question of how to decorate a steel-frame building without pretending it was made of stone. The upper floors were added later and lack his hand. The difference is obvious.
The Monadnock Building at 53 West Jackson Boulevard is the world's tallest load-bearing brick building. Burnham and Root completed the northern half in 1891. Holabird and Roche added the southern half in 1893. The brick walls at the base are six feet thick. The windows are narrow vertical slits. It looks medieval and modern at the same time. Walk inside to see the wavy glass in the original windows and the restored mosaic tile floors. The ground-floor corridor is open to the public.
For the Mies van der Rohe chapter, take the Green Line to the Illinois Institute of Technology campus in Bronzeville. Mies designed the master plan and twenty campus buildings between 1939 and 1958. Crown Hall, at 3360 South State Street, is the climax. A single-span roof held up by eight steel girders, the interior almost entirely free of columns. Mies called it "almost nothing." It houses the architecture school. You can walk the campus for free. The buildings are severe, black, rectilinear. They taught a generation of architects that less really could be less, and that the honesty of materials was more important than ornament. Some people find them cold. Yuki Tanaka finds them precise.
Then go to Oak Park. Take the Blue Line to the Harlem or Oak Park stop. It takes about thirty minutes. Frank Lloyd Wright lived and worked here from 1889 to 1909. His Home and Studio at 951 Chicago Avenue runs guided tours daily for about $20 to $25, depending on the season. The studio wing, added in 1898, has a barrel-vaulted ceiling and a drafting room with a balcony that Wright called the "hangout" for his apprentices. Within a few blocks, you can walk past more than twenty-five Wright-designed houses on your own. The Unity Temple at 875 Lake Street, completed in 1908, is a few minutes' walk north. Wright called it his contribution to modern architecture. It looks like a concrete box from the outside and a jewel box from the inside. Tours are $18. The Hemingway Birthplace is a block away, if you need a break from geometry.
Back downtown, the Chicago Cultural Center at 78 East Washington Street is free and open to the public. It was the city's main library until 1991. The Tiffany dome in the Preston Bradley Hall is 38 feet in diameter and made of 30,000 pieces of glass. It is said to be the largest Tiffany dome in the world. The building itself, designed by the Boston firm Shepley, Rutan and Coolidge in 1897, is a classical pile of marble, mosaics, and stained glass that the city somehow lets you wander through for nothing.
The Harold Washington Library Center at 400 South State Street, completed in 1991, is postmodernism at full volume. Designed by Hammond, Beeby and Babka, it has a red-brick facade, a glass-enclosed winter garden on the ninth floor, and a roof ornamented with four giant aluminum owls. The atrium is open during library hours. The winter garden has a view south over the Loop that most tourists never see, because they do not think to visit a public library.
The Merchandise Mart at 222 Merchandise Mart Plaza is another kind of monument. When it opened in 1930, it was the largest building in the world by floor area. Four million square feet. Art Deco in bulk. The lobby is open during business hours. Walk through it to understand what commercial architecture at scale looks like when it still cares about brass elevator doors and geometric ceiling panels.
For something newer, walk to Millennium Park. The Jay Pritzker Pavilion, designed by Frank Gehry and completed in 2004, is a band shell wrapped in brushed stainless steel ribbons. It looks like a crumpled piece of origami the size of a football stadium. The BP Bridge, also by Gehry, snakes across Columbus Drive and gives you a view of the skyline framed by his own structure. Both are free, always open, and crowded. Go early in the morning if you want to photograph the pavilion without tourists posing in front of every curve.
If you have a day and a car, or the patience for a Metra train, go to Plano, sixty miles west. The Farnsworth House, designed by Mies van der Rohe between 1945 and 1951, is a glass box on steel stilts in the middle of a floodplain. Tours start at $25. It is beautiful, austere, and slightly absurd. The client, Dr. Edith Farnsworth, eventually sued Mies over cost overruns and leaks. Architecture is not always a smooth collaboration.
Graceland Cemetery, at 4001 North Clark Street on the North Side, is worth the trip even if you do not care about the dead. Louis Sullivan designed the Getty Tomb here in 1890. Lorado Taft sculpted the monument to Marshall Field. The cemetery is landscaped and quiet, a park full of stone masterpieces. It is open daily. Admission is free.
What to skip: The Skydeck at Willis Tower and 360 Chicago at the former Hancock Center. Both charge $30 or more for an elevator ride and a crowded observation deck. If you want to see Chicago from above, book a table at the Signature Room on the 95th floor of the former Hancock, order a drink, and look out the window for the price of a cocktail instead of a tourist ticket. The architecture is better at eye level anyway.
Practical notes: The CAC river cruise runs from April to November. Walking tours operate year-round. The L train is the best cheap architecture tour in the city. Ride the Brown Line around the Loop at eye level with office windows and building facades. A single ride is $2.50. A one-day CTA pass is $10, a three-day pass $20. Most major buildings in the Loop are free to enter during business hours, though some lobbies require passing through security. Oak Park is easily reachable by CTA Blue Line. The Frank Lloyd Wright Home and Studio and Unity Temple both require advance tickets in peak season. If you are serious about photographing the buildings, bring a wide-angle lens and shoot early or late. Chicago's flat terrain means the light hits the facades directly at midday, and the shadows disappear.
Chicago's architecture is not a museum. It is a working laboratory. Every generation has added its experiment to the skyline. Burnham and Root invented the skyscraper. Sullivan figured out how to dress it. Wright rebelled against the box. Mies reduced the box to its essence. Goldberg put parking garages in towers. Gang made concrete ripple like water. The next architect is already sketching something on a desk in one of these buildings. The city will let them build it. That is the point of Chicago. It does not preserve its architecture in amber. It keeps building.
By Yuki Tanaka
Architectural photographer based in Tokyo. Yuki captures the dialogue between ancient structures and modern design across Asia and Europe. Her work has been featured in Monocle, Dezeen, and Wallpaper. She sees buildings as frozen stories waiting to be told.