Chicago is a city of firsts — and nowhere is this better seen than in its architecture. The site of the now demolished Home Insurance Building (1884 – 1885), credited as the world’s first skyscraper (at a diminutive 10 stories by today’s standards), you could write a book on the significance of the Chicago cityscape — which is why so many have.

Here are 10 iconic, history-making examples of Chicago architecture, and the many reasons why you should pay them a visit.

1. Rookery Building

209 S. LaSalle St.
Architects: Daniel Burnham & John Root/Frank Lloyd Wright

Rookery Building

On the National Register of Historic Places and designated a Chicago Landmark in 1972, The Rookery is located in Chicago’s downtown Financial District. It was constructed during a transitional period in architectural history, using both load-bearing masonry and a skeletal frame, which are distinguishing elements of the Chicago School of Architecture. Frank Lloyd Wright redesigned the striking two-story skylit lobby in 1905-1907, recasting it in his signature Prairie style. Wright’s work on The Rookery is his only work on any building within the downtown cityscape.

2. Chicago Cultural Center

78 E. Washington St.
Architects: Shepley, Rutan and Coolidge

Chicago Cultural Center

Across the street from Millennium Park and part of the Millennium Park Campus, the “People’s Palace” opened in 1897 to serve two purposes: As the first permanent home for the Chicago Public Library (the building’s Washington Street side), and as the headquarters for the Grand Army of the Republic, the Civil War Union Army veterans’ organization (the building’s Randolph Street side). In 1991, it was rededicated as the Chicago Cultural Center, and became the nation’s first free municipal cultural center, hosting free concerts, art exhibitions and other programming throughout the year.

Listed as a Chicago Landmark and on the National Register of Historic Places, the building was designed in the Classical Revival style, taking inspiration from the monumental structures of ancient Greece and Rome, and the finely detailed buildings of the Italian Renaissance.

Chinese New Year

Architectural elements of note include the Washington Street Lobby, withmosaics of glass, gold leaf, mother of pearl and precious stones; and Preston Bradley Hall, combining glass mosaics with a luminous 38-foot-diameter dome by the Tiffany Glass and Decorating Company of New York. It is, in fact, the largest Tiffany dome in the world, containing approximately 30,000 individual glass pieces.

FREE 45-minute building tours are conducted at 1:15pm from Wednesday through Saturday.

3. Wrigley Building

400 N. Michigan Ave.
Graham, Anderson, Probst & White​

Wrigley Budiling Architecture

Seville Cathedral’s Giralda tower combined with French Renaissance details are the inspiration behind the Wrigley Building. Comprised of two towers of differing heights connected by walkways, the building is clad in glazed terra-cotta, which makes its white façade gleam in the sunlight and evening floodlights. The south clock tower features clock faces of more than 19-feet in diameter, pointing in all four directions. Another striking feature of the building is the fact that, as you walk through the center doors, you find yourself in a secluded park area that overlooks the Chicago River. Which brings me to another reason to visit the Wrigley Building. It sits on the banks of the award-winning Chicago Riverwalk, one of the city’s leading attractions. This 1.25 mile pedestrian-friendly stretch extends from Lake Shore Drive to Lake Street, and features intimate coves, breezy cafes, wineries and bars, public art, monuments, museums, and a boatload of excursions on the water.

4. Tribune Tower

435 N. Michigan Ave.
Architects: Howells & Hood

Exterior of Tribune Tower Chicago

Standing across from the Wrigley Building, a Chicago Tribune competition in 1922, marking the newspaper’s 75th anniversary, inspired a flood of international entries seeking to create “the most beautiful and distinctive office building in the world.”  New York firm Howells & Hood beat out over 250 concepts with its Gothic Revival limestone design, featuring elegant buttresses, intricately carved stonework and an octagonal campanile.

The Crown at Tribune Tower Chicago

As the Chicago Architecture Center explains, the design “used architectural ideas borrowed from the past. The lower office block is sheathed in Indiana limestone with vertical piers and horizontal spandrels characteristic of Art Deco. The building’s crown recalls a Medieval European tower, imitating the Butter Tower of the 13th-century Rouen Cathedral in France. Inside, visitors encounter a Hall of Inscriptions. Carved into the lobby walls are famous quotations from Benjamin Franklin, Voltaire, Thomas Jefferson and James Madison, praising and exalting freedom of the press.”

In keeping with the concept of borrowing from the past, the Tribune Tower’s facade incorporates some 150 fragments from historic buildings and sites, including the Winter Palace in Beijing, Westminster Abbey, London, the Great Pyramid in Giza, The Great Wall of China, and the Parthenon in Athens.

5. TheMART (formerly the Merchandise Mart)

222 N. Merchandise Mart Plaza
Architects: Graham, Anderson, Probst and White

Merchandise Mart

Covering two city blocks and rising 25 stories at the junction of the North, South and Main branches of the Chicago River, theMART was originally developed by Marshall Field & Co. to create a central marketplace where retailers could come to buy their wares all under one roof.

Original designer Alfred Shaw communicated the unique, modern concept of theMART with Art Deco aesthetics and the integration of elements from three building types: the warehouse, the department store and the skyscraper office building.

Art on TheMART

On September 29, 2018, theMART will make history with the launch of Art on theMART, the longest-running and largest digital art projection in the world. The first-of-its-kind for Chicago, this curated series of digital artworks will be projected across 2.5 acres (the equivalent of two football fields) of theMART’s river-facing façade.

6. Marina City

300 N. State St.
Architect: Bertrand Goldberg

Marina Towers

If Marina City looks particularly familiar, it may be because you’re a Bob Newhart fan. The building featured prominently in the opening credits of the Bob Newhart Show. Located along the main branch of the Chicago River in downtown Chicago, Marina City’s distinctive design features two cylindrical 588-foot towers that bear a striking resemblance to corn cobs. At the time of its opening, this designated Chicago Landmark was the tallest residential building and tallest concrete structure in the world. Two notable features of the complex are the House of Blues and the luxury Hotel Chicago, a 354-room Marriott. On the marina level, you can rent a small electric boat and explore the Chicago River.

7. 875 N Michigan Ave (formerly the John Hancock Center)

875 N. Michigan Ave.
Architects: Skidmore, Owings & Merrill

John Hancock Center

One of the world’s most recognized skyscrapers and an iconic example of late-20th century Chicago architecture, 875 N. Michigan Ave. exudes masculine simplicity, with “its expressive structural system and gently sloping façades,” The Skyscraper Center explains. The Center adds that, “The architectural form of 875 North Michigan Avenue represents a radical departure from established aesthetics of the time. Initially, critics labeled the building as too industrial, but over time it has come to symbolize the gutsy tradition of structural expression in Chicago.” Among the skyscraper’s draws for both locals and visitors is The Signature Room on the 95th floor, featuring fine dining with panoramic views of the Chicago skyline and Lake Michigan. What’s more, 360 CHICAGO observation deck is unlike any other. Located 1000 feet above the famed Magnificent Mile, the deck offers breathtaking 360 degree views of the city, and is home to TILT, an enclosed moving platform that literally tilts you over Michigan Avenue from the 94th Floor.

Check out ways to save on 360 Chicago and other top Chicago attractions.

8. One Illinois Center

111 E. Wacker Drive
Architect: Mies van der Rohe


Fittingly, the new Chicago Architecture Center has made One Illinois Center its home. This is one of Mies van der Rohe’s final designs, rising above a former rail yard and the site of Fort Dearborn (1803), the US Army’s westernmost post. When ground broke on One Illinois Center in 1967, it was the first building constructed on the site. It is notable for its International Style, incorporating elements of Mies’ earlier work and the ideas he brought with him from pre-WWII Germany. The International Style is marked by an emphasis on volume, with the use of planes of glass to encase spaces versus masses of brick or stone, and a dependence on the elegance of materials and technical perfection over applied ornamentation. Mies died in 1969, just a year before the building opened.

Chicago Architecture Center

Aside from the significance of the architect and his architecture, One Illinois Center is today known for the newly opened Chicago Architecture Center, a cutting-edge museum that incorporates striking and immersive exhibits, including Building Tall, a room filled with super-sized scale models of famous skyscrapers from around the world, with towering panes of glass that look out upon the Chicago Riverwalk, Wrigley Building and Tribune Tower. For a truly singular experience, hop onto the Chicago Architecture Center’s Architecture River Cruise aboard Chicago’s First Lady CruisesChicago’s #1 tour according to TripAdvisor users.

9. Willis Tower

233 S. Wacker Drive
Architects: Skidmore, Owings & Merrill

Willis Tower Chicago (aka Sears Tower)

Formerly known as the Sears Tower and located in the heart of downtown Chicago, Willis Tower is a 110-story, 1,450 foot ((442.1 m) building, making it the second tallest building in the Western Hemisphere (first place was claimed by One World Trade Center in New York in 2014). In 2009, a multi-million -dollar renovation of the Willis Tower’s observation deck, Skydeck Chicago, was conducted, including the development of The Ledge, a series of glass bays on the 103rd floor that extend from the building to provide visitors with unobstructed views of Chicago through the windows and glass floors – 1,353 feet straight down. In addition to The Ledge, the new Skydeck visitor center features museum-quality interactive exhibits.

Check out ways to save on Skydeck and other top Chicago attractions.

10. Aqua Tower

225 N. Columbus Drive
Architects: Jeanne Gang of Studio Gang Architects

Chicago Architecture Biennial

Bridging the gap between skyscraper and sculpture, the Aqua Tower is located near the shores of Lake Michigan, and, as its name implies, is inspired by the movement and qualities of water. This shimmering multi-use edifice includes the luxury Radisson Blu Aqua Hotel. The design of the 80-story building connects strongly with the outdoors, with terraces that give it its distinctive undulating appearance. Also, a 82,550 sq ft (7,669 m2) terrace features gardens, gazebos, pools, hot tubs, a walking/running track and a fire pit. The Aqua is the recipient of multiple awards and accolades, including the Emporis Skyscraper Award as 2009 skyscraper of the year.

Insider tip

Open House Chicago

Have you ever walked by an interesting Chicago building and wished you could take a peek inside? You’ll get your chance during Chicago’s annual Open House Chicago, a free public festival hosted by the Chicago Architecture Center. More than 200 significant buildings throw open their doors for self-guided tours. Structures located in 20 different neighborhoods range from soaring skyscrapers to opulent mansions and exclusive private clubs, many of which are rarely open to the public. No tickets or registration are required, and you can build your own itinerary based on your must-sees.