High school student Fiona Bueller wants a day off from school and she's developed an incredibly sophisticated plan to pull it off. She talks her friend Candace and her boyfriend Slater into heading to Chicago for the day. While they are taking in what the city has to offer, school principal Edith Rooney is convinced that Fiona is, not for the first time, playing hooky for the day and is hell-bent to catch her out. Fiona has anticipated that, much to Rooney's chagrin.