Adventures in Babysitting 2016

In Oak Park, Illinois, a quiet plan for a special anniversary date falls apart when Mike Todwell cancels, leaving 17-year-old Chris Parker to figure out a way to lift her spirits. To help, she invites her friend Brenda over, and at her mother’s urging she agrees to babysit their neighbors’ eight-year-old Sara Anderson while the parents attend a party downtown in Chicago. What starts as a simple night of babysitting quickly spirals into a wild, cross‑city adventure when Brenda suddenly calls in a panic and runs off to a downtown bus station. Chris is dragged into the chaos by Sara, Sara’s 15-year-old brother Brad, and Brad’s friend Daryl Coopersmith, who persuade her to take the group along for the ride.

On the highway, the station wagon suffers a flat tire, and a tow truck driver known as “Handsome” John Pruitt offers help that comes with a price. Chris realizes she left her purse back at the Andersons’, and Pruitt promises to pay for the tire if they help him out. As the drama unfolds, Pruitt’s own world collides with trouble: a call from his boss Dawson reveals evidence of a wife’s infidelity, and in a violent twist he shoots out a windshield while attempting to confront the lover. This escalation forces Chris and the kids to hide inside the adulterer’s Cadillac, only to be discovered when Joe Gipp, a car thief, steals the Cadillac away from them.

Their escape leads them to a South Side hideout where they’re briefly detained, but they manage to break free. They find themselves in a blues club where the onstage band won’t let them leave until they perform. As the music swells, the group recalls the night’s chaos, and the audience begins to chant and clap along, turning their misadventure into a shared moment of community. The trouble catches up with them again when Joe, Graydon (the operation’s second-in-command), and their boss Bleak arrive, but the club owners stall them long enough for the kids to slip away.

The kids split from Daryl and attempt to reunite with Brenda, but not before a tense chase resumes. They’re separated from a pair of runaways and soon find themselves on the Chicago “L”—only to be caught in the middle of a gang fight. Brad is injured when a switchblade is hurled onto his foot, prompting a dash to the nearest university hospital for a stitch. They then stumble into a fraternity house party, where a kindly donor named Dan Lynch hears of Chris’s predicament and generously donates $45. He drives them to Dawson’s Garage and leaves them there, hoping to set things straight.

Back at Dawson’s, the tall, blond-haired owner with a sledgehammer earns Sara’s mistaken belief that he’s Thor; he denies them the car because of a $5 shortage, but Sara offers him her toy Thor helmet, and he relents, letting them go. Meanwhile, Joe Gipp relays their troubles to Bleak, who and his associates are waiting to tail them. The group then learns that Mike, the boy Chris planned to see, is with another girl, Sesame Blexer, at the restaurant they had hoped to reach. Sara slips away to a toy store, giving Chris a moment to confront Mike. Brad stands up for Chris, though he’s reluctant to strike Mike; Daryl’s bold kick sends Mike crashing into a table, sparking a chaotic scene.

Bleak spots Sara and Graydon pursues her to an office building, where Sara climbs out a window and slides down the façade. The others hurry after her, and they all rush upstairs to help. In a tense sequence, Joe knocksBleak unconscious and passes along a Playboy magazine that contains crucial notes the criminals want to keep hidden. The kids rescue Brenda from the bus station and race home, evading the Andersons on Interstate 290. Once back at the house, Chris cleans up the earlier mess just as the Andersons return. The night ends on a lighter note when Dan arrives with one of Sara’s missing skates, and with Sara’s encouragement, Chris and Dan share a quiet kiss, signaling a new, hopeful chapter after an unforgettable ordeal.