Ferris Bueller's Day Off (1986)

High school student Ferris Bueller wants a day off from school and he's developed an incredibly sophisticated plan to pull it off. He talks his friend Cameron and his girlfriend Sloane into heading to Chicago for the day. While they are taking in what the city has to offer, Dean of Students Ed Rooney is convinced that Ferris is, not for the first time, playing hooky for the day and is hell-bent to catch him out. Ferris has anticipated that, much to Rooney's chagrin.