Chicago’s Architecture: What To See

Chicago’s architecture is the number one reason to visit this midwestern U.S. city. And there is no better way to understand the sweeping accomplishments than to book an architectural walking tour.

While I have visited Chicago countless times for business, I never took the time to be a tourist. In April, I remedied this situation.

CAC First Lady Architecture Cruise

Upon arrival, I immediately booked the CAC First Lady Architecture Cruise. USA Today readers voted it the #1 boat tour in the United States.

“Led by the Chicago Architecture Center’s expertly trained docent volunteers, this 90-minute cruise reveals fascinating stories behind Chicago’s majestic buildings in a way no other tour can.”

It fascinated me to float down the river and see such historic buildings as Willis Tower (formerly Sears Tower), Wrigley Building, Tribune Tower, and Marina City. The tour highlights over 50 buildings in total, including modern landmarks like the Aqua Tower and Navy Pier. 

Bring a jacket even in the summer, as the winds will chill you to the bone. Although you can sit down below, the best views are on the deck! 

An adult ticket costs $56. You can add admission to the center for just $5 (regular price $15) as an event extra.

Chicago Architecture Center (CAC)

I learned how Chicago became “the city of architecture” and explored how design can shape the cities of tomorrow at the Chicago Architecture Center.

Located at 111 E. Wacker Dr., CAC highlights the stories behind the buildings and the visionaries who created them. Nearly 500,000 visitors toured the museum in 2024.

My favorite part of CAC is its 4,250-building scale model of Chicago, featuring more than 4,000 buildings and interactive elements. Check out CAC’s YouTube video celebrating its 50th anniversary.

Great Chicago Fire

Ironically, we should thank Mrs. O’Leary’s cow, who reportedly caused the Great Chicago Fire in October 1871. The legend goes that she was milking her cow in the evening when it kicked over a lantern. The fire destroyed over 17,000 structures over 3.3 square miles, and roughly one-third of the city lay in ruin.

“She was officially exonerated by the Chicago Committee on Police and Fire in 1997, but the legend persists.”—Block Club Chicago

Still, the fire destroyed a large section of Downtown Chicago, including such prominent buildings as the First Baptist Church, the Great Adelphi Theatre, the Michigan Avenue Hotel, Congress Hall, and the St. James Hotel.

The Palmer House

What people might not know is that the original Palmer House—one of the city’s posh hotels for the wealthy—also burned down. Real estate magnate Potter Palmer built the hotel for his fiancée, Bertha.

This 225-room hotel operated for only 12 months at State and Quincy Streets. Potter spent a staggering $100,000 on furnishings. He was also building a second Palmer House nearby. Both hotels burned to the ground on October 8, 1871.

Bertha insisted he rebuild, and the second Palmer House opened in 1873. Then, in 1923, the Palmer Estate razed the building. The third Palmer Hotel cost $20 million. The luxury hotel featured a grand lobby, monumental staircases, bridal suites, dining rooms, ballrooms, a bar, and a barbershop.

“Designed by the firm Holabird & Roche and built during 1923–25, its twenty-five stories housed 2,268 rooms and for a very short time held the record as the world’s largest hotel.”—Chicago History Museum

I recommend visiting the Palmer House to indulge in afternoon tea or a nighttime cocktail. 

The Palmer House Interior

Even if you can’t afford to stay at the Palmer House, you can tour the facility to see Bertha Potter’s extravagant interior design choices.

French muralist Louis Pierre Rigal composed 21 unique frescoes on the lobby’s magnificent domed ceiling.

Louis Comfort Tiffany created the 24-karat gold-dipped chandeliers on the ceiling and the 1.25-ton bronze Winged Angels. 

And you must walk up the Italian marble staircase to the Empire Room and admire the design. The only other similarly constructed staircase can be found in St. Paul’s Cathedral in London. (Check out my tour of the lobby on my YouTube channel.)

Chicago Board of Trade

The Chicago Board of Trade bills itself as “Landmark, Icon, Masterpiece” on its website. This is truly an accurate description. 

This regal 45-story Art Deco skyscraper took my breath away as I stood in its lobby, gazing at the bold, geometric shapes. 

Designed by John A. Holabird and John Wellborn Root Jr.,  the Chicago Board of Trade’s dark windows and spandrels provide its striking vertical emphasis. 

In particular, architectural symbols, such as the sheaf of wheat and bag of corn, intrigued me. They represented the agricultural commodities traded at the exchange.

When you depart the building, be sure to look up at the 31-foot statue that sits atop the building’s pyramidal roof. This 6,500-pound aluminum statue of Ceres (the Roman goddess of grain) clasps a grain sample bag and a sheaf of wheat in her hands. 

The Rookery

Just a few blocks away, I saw The Rookery at the corner of LaSalle and Adams in Chicago’s financial district. Architects John Wellborn Root and Daniel Burnham completed this building in 1888. Frank Lloyd Wright completed the update in 1907. 

You should visit this building to see the two-story lobby, central atrium, oriel staircase, and white marble moldings featuring gold geometric patterning.

The façade incorporates historical decorative elements, including Roman, Venetian, Moorish, and medieval European architectural styles.

Willis Tower (Formerly Sears Tower)

This 110-story skyscraper held the title as the world’s tallest building for 25 years. Chicago natives still refer to it as the Sears Tower, even though it was renamed the Willis Tower in 2009. 

(Another name change is likely. Aon is acquiring Willis Group, and will inherit the naming rights contract for Willis Tower.)

In 1969, Sears Roebuck and Company hired architect Bruce Graham and structural engineer Fazlur Khan of Skidmore, Owings & Merrill (SOM) to design this three-million-square-foot office tower.

Ushering in a new era for Chicago’s skyscrapers, SOM designed a cluster of nine tubes acting together as a single unit to resist wind loads.

In 2015, Blackstone, Inc. purchased the building and initiated its “street to sky” renovation. Recalling the popularity of the original tenant, the Catalog is a multi-level, 400,000-square-foot open lobby which features new dining, entertainment, and retail spaces. In addition, there is a 30,000-square-foot public park on the podium’s roof!

190 South LaSalle

Chicago architects rejected the modernists’ stark steel and glass skyscrapers in the 1980s and 1990s, known as the International style. They ushered in the Postmodernist style. This “architectural u-turn” meant they looked back and incorporated aspects of the city’s proud architectural past, rather than rejecting it.

“This is a common characteristic of Postmodern buildings—oversized scale combined with over-the-top symbolism and in-your-face colors—and depicts the architectural freedom that flourished in the 1980s and ‘90s.”—Chicago Architecture Center

Visit 190 South LaSalle and see this post-modern jewel. It was designed by architects Philip Johnson and John Burgee. 

Located down the block from the Rookery, it evokes this historic building with its reddish-brown masonry.

Merchandise Mart

Chicago likes to lead the world with its architectural accomplishments, so it is no surprise that the Merchandise Mart is ranked as the largest building in the world.

Built in 1930, this 25-story building spans two city blocks. It is adjacent to Orleans Street, Wells Street, and Kinzie Street. It’s located at the junction of the Chicago River.

Designed by Graham, Anderson, Probst & White, this Art Deco building features rows of decorative chevrons (zigzags) while dark spandrels emphasize the building’s verticality. The facade incorporates limestone, terra cotta, and bronze. 

I suggest spending a morning at THE MART to shop in its luxury kitchens and bath retail shops. You should also search for the Art Deco ornamentation and the Jules Guerin murals, which illustrate commerce throughout the world.

Architecture Walking Tours

Multiple companies offer architectural walking tours in Chicago. However, I highly recommend the CAC’s walking tours, such as the “Historic Treasures of Chicago’s Golden Age. An adult ticket costs $35; it is free for CAC members.

“The 40 years between 1890 and 1930 saw the creation of some of Chicago’s most memorable buildings. Tour includes visits to the interiors of the Chicago Cultural Center, Palmer House and Macy’s on State.”

CAC describes this tour as a testament to that era’s ambitions. You will see buildings designed by Daniel Burnham, Louis Sullivan, Holabird and Roche, and other noted architects. But the best part is you’ll hear the stories behind the city’s architectural gems.

I am a huge fan of walking tours, so check out my new GPS-guided walks in the Dupont Circle neighborhood (Washington, DC), Cesis (Latvia), and San Sebastian de la Gomera (Spain).

This article is now featured on GPSmyCity. To download this article for offline reading or create a self-guided walking tour to visit the attractions highlighted in this article, go to Walking Tours and Articles in Chicago.