Chris Parker, a high school senior, reluctantly agrees to babysit the Anderson kids, Sarah and Brad, after her boyfriend cancels their date. When Chris's friend Brenda calls, stranded at a downtown bus station, Chris decides to rescue her. She reluctantly takes Sarah, Brad, and Brad's friend Daryl on the unexpected trip to Chicago. Their night quickly spirals out of control when they experience car troubles on the way, leading them into a series of increasingly dangerous and comedic situations.

As they navigate the city's underbelly, the group encounters car thieves, a street gang, and a daunting blues nightclub, amongst other mishaps. Despite the escalating chaos, Chris strives to keep the kids safe and get them back home before the Andersons return. The evening tests Chris’s ingenuity and bravery as she attempts to solve the problems thrown their way, all while managing to maintain her composure and protect the children from harm. Their escapade turns into a test of endurance and resourcefulness for all involved.