Ferris’s loyal sidekick Cameron Frye lives in a modernist home designed by architect A. James Speyer located in Highland Park. The property’s glass-encased garage plays an important role in the movie. It’s the site where the precious 1961 Ferrari plummets down into the ravine. The North Shore home was on the market for five years before it finally sold in 2014.

Just before the scene at Ferris' dad's office, the film focuses on the then-new 333 West Wacker Drive. The movie was shot in 1985, and the curved high-rise designed by Kohn Pedersen Fox Associates was completed just two years prior. The office tower was the epitome of cutting edge postmodern design at the time and it reflects the bend of the Chicago River in its glassy green facade.

In the movie, Ferris and Cameron speed over to Glenbrook North in the collectible Ferrari to bust Ferris' girlfriend Sloane Peterson out of school. The concrete stairs Sloane walks down are still mostly the same today, and students occasionally recreate the scene. Glenbrook North was Hughes’s alma mater and also served as the setting for The Breakfast Club one year earlier.

If you steal your dad’s Ferrari, how can you not cruise down Lake Shore Drive in the warm weather? It’s perfectly Chicago: skyscrapers on one side, and a clear blue lake on the other. The movie depicts Ferris, Cameron, and Sloane heading south on LSD with the John Hancock Center visible in the distance.

Italian Village on Monroe Street opened in 1927—it still serves up Tuscan fare today and represents one of the last old school Chicago dining rooms. After the trio exit Lake Shore Drive, there’s a shot of them driving past the restaurant’s iconic neon sign.

The garage where the teens drop off the Ferrari (and where the “professional” parking attendant can’t help but take the convertible for a spin) is on Madison Street.

The crew’s first stop downtown? The Sears Tower observation deck—now named the Willis Tower Skydeck. In the movie, Ferris mentions it’s the tallest building in the world which was true through the ’80s and into the ’90s. When the Petronas Towers in Malaysia were completed in 1996, the 1,451-foot tower lost its title. The iconic skyscraper managed to hold onto the claim of highest roof in the Western Hemisphere until 2019.

The Board of Trade shown in Ferris Bueller’s Day Off looks quite different today. In the ’80s, traders wore color-coded jackets, completed sales on paper, and yelled across the pit. Now, that same room is filled with digital screens, computers, and far fewer traders.

Even if you’re Abe Froman the sausage king of Chicago, you won’t be able to get reservations at this fancy French restaurant because it simply doesn’t exist. The exterior shots of the fictional Chez Quis were a private home in Gold Coast which has since been remodeled and doesn’t feature the ivy-covered wall anymore. The interior shots were all filmed in Los Angeles.

Hughes choreographed a memorable montage at the Art Institute of Chicago, one of his favorite places in the city growing up. The three protagonists enter behind a group of school children, and then proceed to be goofballs throughout the massive museum. Then, Cameron comes face to face with Georges Seurat’s A Sunday on La Grande Jatte and has a moment. Meanwhile, Ferris and Sloane find themselves in front of Marc Chagall’s America Windows.

An impromptu musical number at the Von Steuben Day Parade shows the best of downtown Chicago—including the Picasso sculpture at Daley Plaza and Dearborn Street. Requiring nearly 10,000 extras, the scene brought the people of Chicago into the film and was Hughes’s favorite part of the entire movie.

While Ferris is serenading the Germans on a parade float, Cameron and Sloane take a walk through the plaza at the Mies van der Rohe-designed Federal Building and Post Office to talk about what happens after they graduate from high school. You can also spot Calder’s Flamingo sculpture—another beloved Federal Center landmark.