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Ferris, Sloane, and Cameron enjoy the sights, including taking in a Cubs game at Wrigley Field, visiting the Sears Tower, the Art Institute of Chicago, the Chicago Mercantile Exchange, and taking part in the Von Steuben Day Parade, with Ferris lip-syncing to Wayne Newton's 'Danke Schoen' and the Beatles' version of 'Twist and Shout', dedicating the former to Cameron himself. Ferris and his friends arrive downtown and leave the Ferrari with two garage attendants (Richard Edson and Larry Jenkins), who drive off in it a short while later to take a joyride. However, only two people are not convinced by Ferris' deception: his sister, Jeanie (Jennifer Grey), outraged at Ferris' ability to defy authority easily, and the school principal, Edward Rooney (Jeffrey Jones), believing Ferris to be truant. The rest of the school and many residents learn of Ferris' exaggerated illness and offer donations to help 'Save Ferris'. He also has Cameron impersonate Sloane's stuffy-toned father to have Sloane excused for the day due to a faked death in the family.

Ferris persuades Cameron to let them use his father's restored 1961 Ferrari 250 GT 'California' to pick up Sloane (as part of their cover) to travel into the city. He sets up an elaborate ruse in his bedroom with a mannequin, a trophy and his stereo in case anyone decides to check on him. High school senior Ferris Bueller (Matthew Broderick) decides to skip school on a spring day by faking an illness for his parents (Lyman Ward and Cindy Pickett), then encourages his girlfriend, Sloane (Mia Sara), and his pessimistic best friend Cameron (Alan Ruck) to spend the day in Chicago as one of their last flings before they graduate and head off to different colleges.

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