It’s the birthplace of the skyscraper and home to giants like the 1,451-foot Willis Tower—the third tallest building in the United States—and the new-in-2020 St. Regis Chicago at 1,198 feet—the tallest skyscraper in the world designed by a woman—but skyscrapers are only the tip of the iceberg when it comes to Chicago’s dazzling architecture scene. The Windy City’s huge assortment of styles includes nouveau, neoclassical, and art deco gems; Frank Lloyd Wright marvels; and more modernist buildings by Ludwig Mies van der Rohe than in any other city in the world. In fact, you could fill days with stories on Chicago architecture. Even better, opt for an expertly led deep dive with three tours focused on the city’s most fascinating works.
River Cruises on Chicago’s “First Lady” with the Chicago Architecture Center
- Where and when: Cruises depart from the Chicago Riverwalk dock near Michigan Avenue and Wacker Drive (112 E. Wacker Dr.) multiple times a day, seven days a week, from late March to mid-November.
- Tour length: 90 minutes
- Price: From $52
- Buy tickets: via the CAC website
For the best all-around tour of the city’s most impressive structural giants that happens to double as a fun leisure cruise on the Chicago River, you can do no better than the Chicago Architecture Center’s (CAC) river cruises aboard Chicago’s First Lady. These river cruises stand out from others on offer because they’re delivered in partnership with the CAC and always led by the center’s volunteer docent guides. Steve Haddad, an accomplished orthopedic surgeon by trade, is one of those docents. “We’re lucky to have so many time periods and building styles represented here, preserved like a time capsule since the Great Chicago Fire of 1871,” Haddad says. Seeing a nonstop smattering of those styles is among the many perks of this cruise, along with the chance to explore all three branches of the Chicago River for jaw-dropping views of Chicago’s most iconic architecture from the unique vantage point of the water.
This is one of the best ways to take in Willis Tower, Trump Tower, and St. Regis Chicago, the last of which Haddad praises for its striking contemporary style and complex structural engineering components, including its layered glass and blow-through floor. The hits on this architecture cruise keep coming around every river bend: There are art deco gems like the sprawling Merchandise Mart and storied Tribune Tower with its cathedral roof, the art nouveau Lyric Opera House that hovers right above the river like a canyon wall, the white terra-cotta Wrigley Building built by the namesake chewing gum magnate, Harry Weese’s surprising nautical river cottages at the foot of the Kinzie Street Bridge—the list goes on. You’ll find yourself in awe of the cityscape, especially at the end of the cruise, when the boat turns around at the mouth of the river and Lake Michigan for an all-encompassing view of the Chicago skyline.
Guided Tours with the Frank Lloyd Wright Trust
- Where and when: The Chicago bus tour departs from the Rookery building lobby on Thursdays from June to October, 9 a.m. to 4 p.m. Tickets sell out early, so book in advance. Oak Park home and studio tours are offered daily between 10 a.m. and 4 p.m. at 951 Chicago Ave., Oak Park.
- Tour length: Seven hours for Chicago tour; one hour and 45 minutes for Oak Park tour
- Price: $195 for Chicago tour (includes lunch and prosecco toast); $30 for Oak Park tour
- Buy tickets: via the Frank Lloyd Wright Trust website
For serious architecture buffs, no trip to Chicago is complete without a tour of the masterpieces designed by Midwest native Frank Lloyd Wright. Best known for his uniquely American prairie–style homes, Wright’s style was honed during his time in the nearby Chicago neighborhood of Oak Park (about a 20-minute drive from the city), home to more Wright houses than anywhere in the world. But the city also holds a smattering of important works and interior compositions by Wright.
Check out the not-for-profit Frank Lloyd Wright Trust for a choice of tours with expert commentary, including our two favorites. For the ultimate sampling of all things FLW, the seasonal “Wright Around Chicago” takes you on an exclusive small-group tour by bus to the architect’s most notable works across the city. Step inside the Rookery Light Court in the Financial District—one of Chicago’s earliest skyscrapers—as well as Wright’s home and studio in Oak Park where more than 140 buildings were designed. After lunch at a local café, visit the UNESCO-designated Unity Temple in Oak Park before the drive to the innovative Robie House on Chicago’s South Side, considered one of the most influential house designs of the early modern era. A scenic drive along the lakeshore leads you back to the Rookery, where you cap off the tour with a prosecco toast.
For those short on time and keen on lovely nature-inspired houses, head to Oak Park for a combined guided home and studio tour with a self-guided walking tour. The tour is offered all-year round and takes you inside the architect’s domicile and workplace, where the prairie style was born and where your guides point out the ways in which both spaces doubled as experimental laboratories for Wright. Take the self-guided walking tour before or after the guided tour for a look around the historic neighborhood rich in Wright influences.
Bronzeville Tour with TikTok sensation Dilla
- Where and when: Tours depart every other Saturday at 2 p.m. from the south lot of the DuSable Museum of African American History (740 E. 56th Pl., Chicago).
- Tour length: Two hours
- Price: $45
- Book tickets: via the Chicago Mahogany website
“Everything dope about America comes from Chicago,” says lifelong Chicago resident and local historian Sherman “Dilla” Thomas, known for his 60-second TikTok videos on the city’s history. With a combined 150K followers across all the socials, @6figga_dilla’s unique approach to sharing Chicago’s untold stories has also earned him a number of accolades, including the 2022 Chicago Tourism Ambassador of the Year. Dilla is also currently working with Netflix on releasing a historical fiction series based on a real Chicago event.
Visitors to Chicago can experience Dilla’s radical style of history telling live and right at the feet of important architectural works on his Chicago Mahogany Tours. Opt for the popular Bronzeville tour, which accommodates up to 50 people by coach bus. Dilla leads the tour, so imagine the entertaining vibe of his TikTok videos, all while visiting and hopping off here and there to explore sites like the Eighth Infantry Armory—the first of its kind built for an African American military regiment—the Supreme Liberty Life Insurance Building, the Ida B. Wells-Barnett mansion, and Pilgrim Baptist Church, considered the birthplace of gospel music.