Chris Parker is a seventeen year old girl who is waiting for the arrival of her boyfriend, Mike Toddwell, when he arrives, he devastates her by canceling their plans to go to a French Restaurant in downtown Chicago in lieu of his sister becoming ill. Brokenhearted, she has her best friend Brenda come over for a visit, and while she is over, the Andersons call asking if Chris can babysit their daughter Sara. Seeing no other plans for the evening, Chris agrees.When she arrives, she discovers eight year old Sara and her fifteen year old brother Brad in an argument. Sara had taken his Clearasil and used it to paint another picture of her Marvel hero Thor, prompting Brad to call him a homo and upset her. She manages to blackmail him by telling him in front of Chris (without his knowing) that she would tell Chris about all of his love poems to her. Ashamed of his crush, he admits defeat and apologizes. After the Andersons leave for the evening, Brad is visited by his best friend Daryl, whose house he was supposed to be staying over that night, Brad cancels and returns to the living room where he shuts the blinds out from the "stray dog" as he describes him to Chris. Chris gets a call from a frantic Brenda, who had successfully run away from home, but unsuccessfully stranded herself at the bus station downtown. Without the money to pay for a cab ride, Brenda's fear prompts Chris to decide to drive into town. Sara and Brad won't let her leave them home alone, and Daryl's eavesdropping forces her to take him along as well.
In the car, Chris tells Sara a scary story about a man with a hook who kills a babysitter and her children, and when a car tire blowout stands them on the expressway without a spare, she realizes that she forgot her purse at the Anderson's. A tow truck pulls over and "Handsome" John Pruitt offers them a hand, or a hook as much to the surprise and fear to the children. Offering to pay for the tire repair, Pruitt is distracted by a call and he diverts to his home where his wife is cheating on him. In a resulting shootout, Chris and the others get out of the truck and into a Cadillac, which is being stolen. The thief, Joe Gipp promises to take them to safety after he drops off the car at a chop shop. However the leaders of the gang, Greydon and Bleak detain them up in the office for a meeting they were involved in. Daryl boosts a Playboy magazine to replace his dad's which was thrown out of the car window earlier by Brad. They then make a tense escape crossing the girders in the warehouse ceiling, escaping outside. The thieves find the Playboy missing, and as it contains incriminating evidence that can be used against them, they give chase.
The kids are chased into a Blues club where they are not allowed off the stage until they reveal their predicament in song, much to the cheers and applause from the audience. When they are allowed to leave, they are reminded of their mission and predicament when Darryl attempts to pick up a prostitute on the street who turns out to be seventeen that ran away from home. Meanwhile Brenda is not having a very good time at the bus station. Having her glasses stolen while resting leaves her practically blind, she mistakes a sewer rat for a kitten and is laughed at by pest exterminators when she attempts to defend it, she encounters a hot dog vendor who will not accept her small check as payment stating "You slip me the cash, and I'll slip you the wiener." but when she states "I don't have any cash!" he proclaims "Then I don't have a wiener!" Another chase from the thieves prompts them to board a monorail train where a pair of conflicting gang members move in to kill each other. Chris intervenes to hold off the fight until they exit the train, and Brad stands up when she is insulted. Brad gets a knife thrown into his shoe, and Chris wields it against them, quoting her famous line: "Don't fuck with the babysitter." when they back off, the four of them leave the train, and rush Brad to the hospital. After a scare where they think Brad has died, they run into Pruitt again who tells them that they will need to pay $50 for the tire, as he had to pay for the windshield damage from the gunfight earlier.
They arrive shortly after at a fraternity house which is having a Friday night party. Chris meets a new love interest in Dan Lynch who manages to get together $45 toward the car's tire payment. Darryl gets into trouble with a jock whose lonely girlfriend attempts to have sex with him, and Dan takes them to Dawson's garage. Leaving, and expected never to be seen again as he did not give Chris an address to get ahold of him to pay him back. Upon entering the garage, they meet Dawson, whose long blond hair and physically fit appearance causes Sara to think he is the alter ego of Thor. Dawson, offended by the $5 shortage refuses to relinquish the car, but Sara's selflessness in giving him her plastic Thor helmet prompts him to have a change in heart, he gives the car and her helmet to the kids and lets them go.
Enroute to the bus station, Chris spots the restaurant that Mike was supposed to take her to that night, and Darryl points out Mike's car in the parking lot. They go in to find that Mike is dating and flirting with the sleazy Sesame Plexer, and it is revealed that Mike was only dating Chris in interest of having sex with her. Brad stands up for Chris, but won't sink to his level. Darryl admits "I will" and kicks Mike into a desert cart. Meanwhile, Sara slipped out of the restaurant to visit a toy store she had seen coming down the street, and is approached by Bleak who spots the Playboy in her backpack. They chase her down to the building that her parents are having their party in and find through chocolate finger smudges on the elevator buttons which floors to check. Graydon exits in the renovated top floor of the building, and discovers Sara climbing out the window on a rope. Chris, Darryl and Brad hot on their trail choose the wrong floor and accidentally crash the Anderson's office party. After a brief encounter with Bleak, both he and Chris notice Sara walking along the glass window ledge outside, Chris causes Bleak to trip while she and Brad and Darryl go upstairs and discover Sara outside the window. After pulling her up to safety, Joe arrives and explains they were after the Playboy the whole time. They decide to leave Graydon outside and let him "Sweat a little while" Joe shows his resignation from the car thieves by punching out Bleak and they depart the building.
Brenda discovers her glasses and steals them back, only to be chased from the bus station by all the encounters she had come across. Being chased by the homeless, she runs into the exterminators, past the hot dog vendor and past the phone booth which is a homeless man's house. After she gets outside, she is picked up by Chris and the others and she proclaims "What took you guys so long?!" on the way home, the kids pass the Andersons in their trip home, they travel at 80mph to get home. Chris sends the kids upstairs and Brenda home before cleaning up the messes that had been made earlier in the day. Coming to settle down just as the Andersons appear in the doorway, not suspecting a thing. Chris goes upstairs to say good night and announces her plans to retire from Babysitting. They each admit to each other and thank themselves for "What was probably the greatest night of their lives... so far"
As Chris leaves, Dan makes a surprising appearance to return Sara's skate which she left in his jeep, as well as admit to Chris that he is interested in her. Sara shouts "Kiss him!" from the bedroom window, and they comply happily. Brad, who had come to realize that while they aren't boyfriend/girlfriend he and Chris can still have a good friendship, and accepts that Dan is better for her than he is. He closes the blinds to give the two some privacy, and the credits roll.
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