Justin and Cory go back to the summer of 1987, a simpler time when $40 was enough to get you out of any tight spot. Elisabeth Shue proves she's the world's greatest blues singer/babysitter in, Adventures in Babysitting.

PLOT

*Spoilers Ahead*

After her boyfriend Mike (Bradly Whitford) unexpectedly cancels their anniversary date, Chris Parker (Elisabeth Shue), convinced by her mother babysits the Andersons' kids, Sara (Maia Brewton) and Brad (Keith Coogan) while they attend a party in Chicago. After receiving a frantic phone call from her friend Brenda (Penelope Ann Miller), who ran away to the bus station downtown and became stranded, Chris plans to go alone to pick her up, but is coerced by Brad, Sara and Daryl (Brad's Friend/Anthony Rapp) to take them with her. On the freeway, the Buick Electra station wagon suffers a flat tire and they are picked up by a kind tow truck driver, "Handsome" John Pruitt (John Ford Noonan), who offers to pay for the tire when Chris realizes she left her purse at the Andersons'. En route, Pruitt gets a call from his boss Dawson (Vincent D'Onofrio) with evidence that his wife is cheating on him, and he rushes to his house to confront the infidelity; Chris's mother's car is damaged when Pruitt accidentally shoots out the windshield with a revolver while aiming to kill his wife's lover. Chris and the kids hide in the adulterer's Cadillac, which is then car-jacked by a thief named Joe Gipp (Calvin Levels).

Reaching their hideout in the South Side, the kids realize they have stumbled upon a chop shop, and Joe is punched and chided by Graydon (Ron Canada), the operation's second-in-command, for bringing potential witnesses. They are detained in an upstairs office but manage to escape over the rafters and through a window, whereas Joe spots them but does not alert Graydon. They enter a blues club where the band on stage won't let them leave until they sing the blues. Chris, Brad, Sara and Daryl recount their events so far that night to the cheers of the audience and are allowed to leave, successfully losing Graydon and his leader Bleak (John Chandler). Meanwhile, Brenda is having trouble of her own; after her glasses are stolen she mistakes a sewer rat for a kitten and is appalled when pest control points it out, as well as arguing with a hot dog salesman who only takes cash.

They are then found and chased again by Greydon and Bleak, but manage to escape on the Chicago 'L' train and wind up in the middle of a gang fight in which Brad is injured when one of the gang leaders throws a switchblade onto his foot. They take Brad to the hospital, where he receives a single stitch to his toe, while the rest are led to believe he had died. They run into Pruitt, who tells the kids he replaced the windshield, but they need to pay Dawson $50 for the tire. The kids come across a fraternity house party and Chris meets and becomes attracted to Dan Lynch (George Newbern), a gentleman who learns of Chris' problem and donates $45 to help. He takes them to Dawson's Garage and drops them off. When they find Dawson, his blond hair and sledge hammer leads Sara to believe he is her hero Thor. He coldly denies them their car because of the $5 shortage, but when Sara offers him her toy Thor helmet, he changes his mind and lets them go. Meanwhile, Joe Gipp told Bleak about their troubles and the three are waiting to follow them. The kids find the restaurant where Mike was supposed to take Chris and discover he is there with another girl. Sara slips away on her own to look at a toy store while Chris yells at Mike. Brad stands up for his friend while Daryl kicks Mike into a food cart, ruining the dinner. Meanwhile, Sara is spotted by Bleak, and Graydon chases her to an office building where she goes into hiding on a floor being renovated; the others note her disappearance and follow, accidentally coming across the Andersons' party at the same time.