A high school slacker decides to skip school and embark on an adventure through downtown Chicago, bringing along his girlfriend and his excessively anxious best friend. Despite being a habitual truant, he’s an expert at duping adults, including his naive parents and the school's dogged principal, who’s hell-bent on catching him. Using an elaborate scheme involving a dummy, sound effects, and a pre-recorded answering machine message, the protagonist manages to make everyone believe he is seriously ill and bedridden.

The trio's escapade includes borrowing the best friend's father's prized Ferrari and visiting various landmarks, such as the Sears Tower, a fancy restaurant, and an art museum. The experiences they share throughout the day help them bond, bringing them closer while providing much-needed liberation from the pressures of teenage life. Meanwhile, the principal’s mission to expose the hooky-playing student's truancy becomes a personal vendetta, leading to a string of comic misadventures. Concurrently, the protagonist's sister, fueled by a mix of envy and disdain for his rebellious antics, is determined to unravel his deceit. All the while, the protagonist offers cheeky asides to the audience, sharing his philosophy on life and the importance of taking a break to enjoy it.