Chicago City Break: A 40-Year Journey on the Ferris Bueller Trail
Following Ferris Bueller's Chicago Footsteps 40 Years On

"Life moves pretty fast. If you don't stop and look around once in a while, you could miss it." This iconic line from the 1986 film Ferris Bueller's Day Off feels more resonant than ever, four decades after the movie was shot on location in Chicago. As the film celebrates its 40th anniversary in 2026, a return to the Windy City offers a perfect chance to explore its unique blend of cinematic history and vibrant culture.

More Than Just a Film Set: The Heart of Chicago

While Chicago is a star of the silver screen, featuring in everything from The Dark Knight and The Bear to Home Alone, its true appeal runs much deeper. This is a city of fascinating contrasts, where the legacy of the Prohibition era lives on in secret speakeasies, smoky jazz bars like the 40-year institution Rosa's Lounge sit alongside glossy skyscrapers, and the vast expanse of Lake Michigan provides a constant, calming backdrop to the urban energy.

The city's geography is key to its character. You can easily walk from the bustling downtown centre to the serene lakefront, escaping the metropolitan buzz at will. This accessibility, combined with a fiercely proud local culture centred on food, drink, and music, makes Chicago a wonderfully underestimated destination for British tourists.

Following the Bueller Itinerary: Stays and Secrets

For an immersive experience, a stay at the historic Chicago Athletic Association Hotel on Michigan Avenue places you at the heart of the action. With views of Millennium Park and the famous Cloud Gate sculpture (The Bean) from its rooms, the hotel is a destination in itself, rich with gothic detail and preserved original features like marble tiles and stained glass.

Venturing out, the cultural options are myriad. Visitors can engage with the eccentric Yoko Ono: Music of the Mind exhibition at the Museum of Contemporary Art (running until 22nd February 2026), or explore literary history at the American Writers Museum. For a truly unique Chicago evening, the Chicago Magic Lounge offers an unforgettable experience, entered via a secret door in a laundrette.

Essential Chicago Tips for the Modern Explorer

To make the most of a city break, savvy planning is key. A Chicago CityPASS® ticket can save 48% on combined admission to top sights like the Skydeck Chicago and an architecture river cruise. For foodies, the Yes Chef Chicago: A Bear-Inspired Food Tour takes you to the real restaurants featured in the hit TV show.

Must-visit spots include the First Lady Chicago Architecture River Cruise for stunning skyline views, and the atmospheric Tortoise Supper Club for prime rib and live jazz. Don't miss a walk through picturesque Lincoln Park, perhaps with a free local greeter guide, to hear the area's insider stories.

Ultimately, Chicago proves itself to be far more than a filming location. It is a city with immense heart, depth, and a compelling history that invites visitors to stop, look around, and fully immerse themselves—just as Ferris Bueller famously advised.