Chicago City Break: A Ferris Bueller-Inspired Tour 40 Years On
Chicago City Break: Following Ferris Bueller's Footsteps

"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 in Chicago, the city remains a captivating contradiction of history, culture, and pure cinematic energy, often overlooked by British tourists in favour of New York or Los Angeles.

Chicago is a city you have likely seen on screen far more than you realise. While many flock to New York for movie spots, they might be surprised to learn that Chicago has frequently doubled for the Big Apple. From the Home Alone franchise to The Dark Knight, where it transformed into Gotham City, and hit series like The Bear and Ozark, its filmography is extensive. Even Emily in Paris has filmed scenes here.

More Than Just a Film Set: The Heart of Chicago

Beyond the official filming notices plastered on lampposts, Chicago possesses a profound depth. Its fascinating history unfolds through smoky jazz bars, Prohibition-era speakeasies, and glossy skyscrapers that glint over Lake Michigan. The city's geography is central to its character; you can easily walk from the downtown bustle to the serene lakefront, escaping the urban madness at will.

For a return visit steeped in this atmosphere, the historic Chicago Athletic Association Hotel on Michigan Avenue is an ideal base. From a fourth-floor room, you can see the famous Cloud Gate sculpture (The Bean) in Millennium Park, with views stretching to the lake. The hotel itself, a former athletic club, buzzes with life in its gothic, marble-tiled hallways, preserving a bygone era in its dark wood and stained glass.

Experiencing the City's Cultural Pulse

Venturing out, the cultural options are myriad. You can engage with the eccentric Yoko Ono: Music of the Mind exhibition at the Museum of Contemporary Art (until 22 February 2026) or explore literary history at the American Writers Museum. As night falls, Chicago's spirited nightlife comes alive. Rosa's Lounge, a 40-year institution, offers authentic jazz, while the Chicago Magic Lounge provides a uniquely Chicagoan experience, entered via a secret door in a laundrette.

Top Recommendations for Your Visit

Stay: The Chicago Athletic Association Hotel for its history and perfect location.
Admire: The First Lady Chicago Architecture River Cruise for stunning skyline views.
Taste: The Yes Chef Chicago: A Bear-Inspired Food Tour to sample dishes from the hit show.
Explore: Lincoln Park with a free greeter guide for insider stories.
Hack: Save 48% with a Chicago CityPASS® ($139 for adults), covering top attractions like the Skydeck and architecture tours.

From a prime rib dinner at the Tortoise Supper Club to a fresh pretzel at the historic Berghoff restaurant, the city's food scene is fiercely proud. Chicago is a wonderfully underestimated destination with heart, history, and a magic that even Ferris Bueller would approve of.