Discover Chicago’s Remarkable Architecture—Here’s Your Guide

As the birthplace of the skyscraper, Chicago boasts architectural giants like the 1,451-foot Willis Tower—the third tallest building in the U.S.—and the recently unveiled St. Regis Chicago at 1,198 feet, the tallest skyscraper designed by a woman. However, skyscrapers are just a glimpse of the city's rich architectural landscape. The Windy City showcases a diverse array of styles, including nouveau, neoclassical, and art deco treasures, along with masterpieces by Frank Lloyd Wright and a plethora of modernist designs by Ludwig Mies van der Rohe, more than any other city globally. You could easily spend days uncovering the stories of Chicago’s architecture, or better yet, join a guided exploration with three tours centered on the city's most intriguing structures.

Chicago’s “First Lady” River Cruises with the Chicago Architecture Center

• Departure details: Cruises leave from the Chicago Riverwalk dock located near Michigan Avenue and Wacker Drive (112 E. Wacker Dr.) multiple times daily, seven days a week, from late March to mid-November.
• Duration: 90 minutes
• Cost: Starting at $52
• Purchase tickets: through the CAC website

For a comprehensive tour of the city’s most impressive architectural wonders, which also serves as an enjoyable leisure cruise on the Chicago River, look no further than the Chicago Architecture Center’s (CAC) river cruises on Chicago’s First Lady. These cruises distinguish themselves from others by being hosted in partnership with the CAC and always led by knowledgeable docent guides. Steve Haddad, an orthopedic surgeon, is among the dedicated docents. “We’re fortunate to have such a range of time periods and architectural styles preserved here, like a time capsule since the Great Chicago Fire of 1871,” Haddad explains. This cruise offers a continuous showcase of those styles, along with the unique opportunity to explore all three branches of the Chicago River for breathtaking views of the city’s most iconic architecture from the water’s perspective.

This is a fantastic opportunity to admire Willis Tower, Trump Tower, and St. Regis Chicago, the latter of which Haddad highlights for its stunning modern design and intricate structural elements, such as its layered glass and blow-through floors. The architectural marvels on this river cruise continue to impress with every turn: from the expansive art deco Merchandise Mart to the historic Tribune Tower crowned with its cathedral-style roof, the art nouveau Lyric Opera House soaring above the river, and the white terra-cotta Wrigley Building, commissioned by the famous gum mogul. Don't miss the charming nautical river cottages by Harry Weese at the Kinzie Street Bridge—the list is extensive. By the end of the cruise, as the boat pivots at the confluence of the river and Lake Michigan, you’ll be left in awe of the breathtaking Chicago skyline.

Guided Tours Offered by the Frank Lloyd Wright Trust

• When and where: The Chicago bus tour departs from the lobby of the Rookery building on Thursdays from June through October, running from 9 a.m. to 4 p.m. Tickets tend to sell out quickly, so advance booking is recommended. Daily tours of the Oak Park home and studio are available from 10 a.m. to 4 p.m. at 951 Chicago Ave., Oak Park.
• Duration: Seven hours for the Chicago tour; one hour and 45 minutes for the Oak Park tour.
• Cost: $195 for the Chicago tour (includes lunch and a prosecco toast); $30 for the Oak Park tour.
• Purchase tickets: via the Frank Lloyd Wright Trust website

For architecture enthusiasts, no visit to Chicago is complete without exploring the stunning designs of Midwest native Frank Lloyd Wright. Renowned for his distinctive prairie-style homes, Wright developed his unique aesthetic in the nearby Oak Park neighborhood—the location of more Wright-designed houses than anywhere else in the world. The city itself also features several significant Wright works and interior designs.

Explore the non-profit Frank Lloyd Wright Trust for a selection of tours led by knowledgeable guides, including our top two recommendations. For a comprehensive experience of all things FLW, the seasonal “Wright Around Chicago” offers an exclusive small-group bus tour of the architect’s most renowned works throughout the city. Visit the Rookery Light Court in the Financial District—one of Chicago’s earliest skyscrapers—along with Wright’s home and studio in Oak Park, where over 140 structures were crafted. After enjoying lunch at a local café, you'll head to the UNESCO-designated Unity Temple in Oak Park before visiting the groundbreaking Robie House on Chicago’s South Side, regarded as one of the most influential home designs of the early modern period. A scenic lakeshore drive brings you back to the Rookery, concluding the tour with a celebratory prosecco toast.

If you're short on time but eager to see beautiful nature-inspired homes, visit Oak Park for a guided tour of Frank Lloyd Wright's home and studio, combined with a self-guided walking tour. Available year-round, this tour takes you into the architect’s residence and workplace, where the prairie style originated, while your guides highlight how both locations served as experimental hubs for Wright's designs. You can take the self-guided walking tour before or after to explore the historic neighborhood rich with Wright's influence.

Bronzeville Tour Featuring TikTok Star Dilla

• When and where: Tours take off every other Saturday at 2 p.m. from the south lot of the DuSable Museum of African American History (740 E. 56th Pl., Chicago).
• Duration: Two hours
• Cost: $45
• Reserve tickets: through the Chicago Mahogany website

“All the cool things about America come from Chicago,” says local historian and lifelong resident Sherman “Dilla” Thomas, who is famous for his 60-second TikTok videos sharing the city’s history. With a combined following of 150K across social platforms, @6figga_dilla has garnered accolades, including the 2022 Chicago Tourism Ambassador of the Year. Dilla is also collaborating with Netflix to produce a historical fiction series inspired by a real Chicago event.

Visitors to Chicago can experience Dilla’s unique storytelling style in person on his Chicago Mahogany Tours. Join the popular Bronzeville tour, which accommodates up to 50 people in a coach bus. Dilla leads the tour, bringing the lively energy of his TikTok videos as you explore significant sites like the Eighth Infantry Armory—the first built for an African American military unit—the Supreme Liberty Life Insurance Building, the Ida B. Wells-Barnett mansion, and Pilgrim Baptist Church, known as the birthplace of gospel music.