13 Ways to See Chicago’s Best Architecture

One of the best ways to soak up Chicago’s architecture is while cruising—slowly—along the Chicago River in downtown Chicago. Leave the navigation to either of these four companies: Wendella, Shoreline Sightseeing, Chicago Architecture Center, and Chicago River Boat Architecture Tours. Each tour is narrated and lasts between 45 minutes and 90 minutes. Note that they do not operate during the winter months, and reservations are highly recommended.

Related: The Best Things to Do in Chicago

Known for his Prairie style and organic architecture, Wright raised his family in a home he designed in Oak Park and built in 1889. He also used it as a drafting studio. Today, you can take a guided tour and witness restoration work done by the Frank Lloyd Wright Preservation Trust, who have turned back the clock to how it would have looked in 1909, featuring Wright-designed textiles and furniture. There are two guided tours: one lasting an hour and covering the interior, and the other focused on the interior and exterior, for an hour-and-45-minute experience.

While this cultural center (a former—and the first—Chicago Public Library branch) is already awesome on its own—with rotating art exhibits and no fee to enter—viewing the Preston Bradley Hall Tiffany Dome is a real treat for any architecture lover. At 38 feet in diameter and installed in 1897, based on Louis Comfort Tiffany’s design, this is the largest Tiffany-glass dome in the world. In 2008, it received a major restoration.

For a broad overview of some of Chicago’s most significant skyscraper designs, this 90-minute walking tour organized by Chicago Architecture Center achieves just that, taking you to projects designed by Bertrand Goldberg (Marina City) and Mies van der Rhoe (IBM Building). Also on the tour is Chicago’s fourth-tallest building: the 83-floor AON Center, completed in 1973 and a result of the design partnership between Perkins and Will and Edward Durrell Stone.

Near the University of Chicago’s campus, in the South Side neighborhood of Hyde Park, Wright’s Prairie-style commission—the best example of his Prairie-style homes—was built in 1910. There are three different guided tours offered by the Frank Lloyd Wright Trust, which shepherded a recent restoration unveiled in 2019: a 90-minute, in-depth tour; 45-minute interior tour; and 90-minute combination guided and self-guided audio tour.

Before arriving at the Art Institute of Chicago in 2018, this stained-glass window (referred to as the Hartwell Memorial Window) designed by Louis Comfort Tiffany was at the Central Baptist Church in Providence, Rhode Island. The 48-panel window was commissioned by a woman a century ago, in honor of her husband, and the move to the museum (find it in the Henry Crown Gallery at the top of the staircase) also includes conservation.

Born in Germany, Ludwig Mies van der Rohe was the last director of the Bauhaus school of art, working alongside artists like Le Corbusier. After World War II he emigrated to Chicago to head up the Illinois Institute of Technology’s architecture department between 1938 and 1958, also designing buildings on the 120-acre campus in the Bronzeville neighborhood. On a two-hour walking tour, you can see each of these buildings as all are still standing.

As the current home of the Unitarian Universalist Congregation in Oak Park, this 8,000-square-foot building with a fortress-like façade was completed by Wright in 1908 and born out of concrete. It underwent a major, four-year restoration that wrapped in 2017. Opt for either a guided 45-minute interior tour or 90-minute in-depth tour, both organized by the Frank Lloyd Trust, or—if time is tight—an audio self-guided tour at your own pace.

Want to see the tallest skyscraper designed by a woman? Completed in 2020, based on Jeanne Gang and Gang Studio’s design, this 101-story building, referred to as Vista Tower, is home to the recently opened St. Regis Chicago, which has 191 hotel rooms within. Interesting fact: another of Gang’s Chicago projects—Aqua—is the second-tallest building designed by a woman, clocking in at 87 floors.

If you arrive in Chicago via certain Metra lines or any Amtrak route, you’ll access Union Station in downtown Chicago. But to go deeper and learn more about its Beaux-Arts architecture and fascinating history (as the country’s third-busiest train station), sign up for an hour-long walking tour, which includes entry into the Great Hall. Daniel Burnham designed the station, unveiling it in 1925 after ten years of construction.

A major part of the American Arts & Crafts movement, Tiffany glass has a large presence in Chicago today, resulting from meticulous restoration. In fact, the city hosts one of the country’s largest collections of Tiffany glass. This 90-minute tour organized by the Chicago Architecture Center takes you to some of those sites, including a Tiffany dome inside Macy’s.

This 90-minute walking tour showcases some of the works by esteemed architect Louis Sullivan—who employed Wright at his architecture firm, Adler & Sullivan, between 1888 and 1893—and takes you to buildings he designed in the Loop, including the Jewelers Building and Sullivan Center. Sullivan’s often referred to as the “father of skyscrapers” and an early adopter of the mantra “form follows function.”

Another of Burnham’s designs—in collaboration with John Wellborn Root—is an architectural marvel completed in 1888, resembling a Moorish castle on the interior. On an hour-long tour organized by Chicago Architecture Center, you’ll learn about the many thoughtful restorations over the years that have kept this building in tip-top shape, including a 1905 lobby makeover by Wright.