Wanderlust for One

The world on your own terms

Chicago Architecture Highlights: 5 Must-Dos

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Several American cities hold a special place in my heart, but when it comes to indulging my appreciation for great architecture, Chicago stands head and shoulder above its peers. This Midwestern city, with its rich history and occasionally tumultuous past, is also home to some seriously gorgeous buildings and innovative structures.

A view of the Chicago cityscape as seen from the Wabash Bridge. A newly sprouting tree branch can be seen in the foreground, while the Chicago River, with the bridge spanning it, and tall skyscrapers are displayed before a blue sky.

So on a recent solo visit, I took the opportunity to experience several of the city’s architectural gems up close and in person, and I had the best time. One of the best parts of traveling alone is being able to take your time exploring the things that strike your fancy–and that’s exactly what I did. If you have an interest in architecture, visiting Chicago as a solo traveler is veritable smorgasbord.

Chicago Architecture Highlights

Visit the Chicago Architecture Center

The glass facade of the Chicago Architecture Building reflecting the cityscape

Begin your explorations at Chicago Architecture Center, located right in the heart of the Magnificent Mile, overlooking the Chicago River, and in close proximity to many of the city’s most iconic structures. Dedicated to telling the story of the city’s buildings and infrastructure, the Center offers an incredible, interactive scale model of the city, which you can control to witness how the Great Fire of 1871 spread across the city, ultimately shaping its future. Other exhibits highlight how Chicago continues to innovate as a city that takes pride in its built spaces. 

Take a Boat Tour

I’ll always take an opportunity to explore a new-to-me city on the water, and in Chicago, it’s practically a requirement. Several companies, including the Chicago Architecture Center, offer tour options for floating down Chicago’s rivers while a knowledgeable tour guide narrates, pointing out buildings of note. I experienced Chicago on the water as part of a Wendella Boats and Tours excursion. It was almost the best 90 minutes of my time in the Windy City, with the added bonus of catching the sunset from our boat.

People on a boat looking up at a city skyline
The Wendella Boat Rides launch below the Wrigley Building in Chicago.
The sun setting behind a cityscape, as viewed from a boat on the water

Explore the University of Chicago Campus

During my time in Chicago, I took a bus from downtown to the South Side to amble around the University of Chicago’s campus. I hate to say it, but this neo-Gothic campus puts others to shame. It’s not all Gothic, though. Like many other older colleges and universities that have grown over time, the University of Chicago campus boasts a broad mix of architectural styles. It was truly a highlight to sit on a bench, people watching prospective students touring the campus with their families. But that’s not all.

A photo of a few people walking on a walkway on a college campus.
A wide angle photo showing the architecture inside the Reynolds Club Student Center on the University of Chicago campus.
Detail of a carving on the Reynolds Club building at University of Chicago.
Three arched windows in the neoGothic style, covered in vines

Pay Homage at the Frederick Robie House

Y’all. Not only is the University of Chicago a true Gothic wonderland—it also boasts a Frank Lloyd Wright designed home. The Robie House—designed for Frederick Robie who, coincidentally, never lived in it—served at one time as a seminary dormitory and as a frat house. Today, the home is preserved as an example of Wright’s work and impact, and you can take a tour with a knowledgeable docent to learn more of the home’s history all while taking in the long horizontal lines that are a hallmark of Wright’s Prairie style.

External view of a brick, prairie style home
Stained glass window details
A wide angle view of the living room area in the Frederick Robie house

Carbide and Carbon Building/Pendry Hotel

Now home of the Pendry Hotel, the famous Carbide and Carbon Building, built in 1929, is a modern work of art, both outside and inside. From the façade—as any good docent on a boat tour will tell you—the building seems to have been designed to look like a giant bottle of champagne, complete with dark green marble and gold foiling at the top. Inside, the gilt Art Deco lobby of the-now Pendry Hotel is a breathtaking masterpiece.

A skyward view showing the front façade of the Pendry Hotel, formerly the Carbide and Carbon Building in Chicago's Loop neighborhood.
Detail view an an engraved brass door of the elevator at the Pendry Hotel in Chicago.
Detail view an an ornate grate in the Pendry Hotel in Chicago.
The intricate designs of the window of the bar at the Pendry Hotel in Chicago.

More Notable Highlights

  • Tribune Tower – Once home to the Chicago Tribune and the outcome of an international design competition to create “the most beautiful building in the world,” this neo-Gothic wonder is on the shortlist for a deeper dive on my next visit to Chicago.
  • The Merchandise Mart – A thrilling example of Art Deco design, the Merchandise Mart served as a stunning backdrop for the annual open air “Art on the Mart” digital projection light show. I only got to see some of the details from the outside, but it certainly bears closer inspection.
  • Marshall Field and Company Building – I’m not gonna lie—I’ve been to Macy’s all over America, but I’m not sure I’ll ever see one like the one on State Street in Chicago. Housed in the former Marshall Field’s Department Store building, the structure’s Classical Revival features hearken back to another time in the city’s past. Next time, a deeper dive.

Chicago is well known for many other things—great food, city life, art, and seriously immaculate vibes, but if you pass on the opportunity to witness the city’s commitment to preserving its history through its buildings, you’re truly missing out.