Recreating the film within the space of a single school day turns out to be a logistical impossibility, and my expenses can't stretch to borrowing a red 1961 Ferrari 250 GT California Spyder like the eponymous hero. So I embrace Ferris' mantra — "Life moves pretty fast. If you don't stop and look around once in a while, you could miss it" — and spread my visit across five days.
Unlike New York, where every offer of assistance is predicated on the expectation of a tip, in Chicago, the smiles are unconditionally warm and genuine.
I'm in a Ferris state of mind as I begin my nostalgia-steeped odyssey 40km north of downtown Chicago, in the Illinois suburb of Highland Park, location of the modernist Ben Rose House, which served as Cameron's home. With its detached garage on pylons set on the edge of a densely wooded ravine, the striking glass and steel residential structure still looks achingly cool more than 60 years after it was built.
A short drive south lies the village of Northbrook, where I meet Judy Hughes — no relation to the director — president of the local historical society. John Hughes spent his formative years in Northbrook — renamed Shermer in the film — and Judy shepherds me among featured locations, including Glenbrook North High School and the 62-year-old white water tower that was painted with the words "Save Ferris" but is slogan-free now.
When Ferris and his friends first arrive in Chicago, they get a bird's-eye view at Sears Tower. In 1986 the 110-storey structure — now rechristened Willis Tower — was the tallest building in the world. Today the downtown monolith of gleaming black aluminium boasts an observation Skydeck on the 103rd floor and The Ledge — four glass balconies with vertigo-inducing views.
Mimicking the film, I press my forehead against the glass and look down 412m to South Wacker Drive. My head spins, my legs shake violently as if they're about to buckle and I feel I might outdo Ferris and "barf up a lung".
On my second evening, I seek culinary nirvana at the elegant Italian dining room, Spiaggia. Against a panoramic backdrop of Lake Michigan, the nine-course tasting menu of award-winning chef Tony Mantuano seduces me with flavourful Sardinian parcels called culurgiones, a moreish nest of pasta glistening with pressed garlic in olive oil, and a heavenly deconstructed tiramisu.
I spend the following day prostrate at the altar of one of Chicago's religions: baseball. A tour of Wrigley Park, home of the Chicago Cubs and the second-oldest ball park in the league dating back to 1914, is crammed with fascinating facts, courtesy of our humorous guide, Robert.
Excitement is palpable in the surrounding neighbourhood bars of Wrigleyville before I take a pew in the outfield area, where Ferris sat, for a game against the Cincinnati Reds.
A pair of majestic bronze lions with a striking green patina proudly guards the entrance to The Art Institute of Chicago the next morning. Inside I'm crestfallen that there are no schoolchildren to help me recreate Ferris, Cameron and Sloane's whimsical hand-in-hand traipse past Rodin's expressive bronze cast, Adam.
Instead I meander through four labyrinthine buildings to survey John Hughes' favourite works, shown in the film, including Edward Hopper's Nighthawks and Marc Chagall's blue stained-glass American Windows.
I eventually settle, like Cameron, in front of Georges Seurat's evocative Pointillist painting, A Sunday On La Grande Jatte, while listening to a arrangement of The Smiths' lament, Please, Please, Please, Let Me Get What I Want. Staring at those coloured dots, I feel I have.
IF YOU GO
Getting there: American Airlines flies from Auckland to Chicago, via LA.
Further details: See visittheusa.com.