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Bob and Cindy Russell and their three kids, 15-year-old Tia (Jean Louisa Kelly), 8-year-old Miles (Macaulay Culkin), and 6-year-old Maizy (Gaby Hoffmann), have recently moved from Indianapolis, Indiana to the Chicago, Illinois suburbs because of Bob's promotion. Tia resents her parents for the move. Late one night, they receive a phone call from Indianapolis informing them that Cindy's father has suffered a heart attack. They make plans to leave immediately to be with him. After hearing the news, Tia accuses Cindy of abandoning her father.
Bob suggests asking his brother, Buck (John Candy), to come watch the children, to which Cindy objects. While they are middle class suburbanites, Buck is an unemployed slacker, who lives in a small apartment in the city, enjoys drinking and smoking, and earns his living by betting on rigged horse races. He drives an old and crackling 1977 Mercury Marquis (every time he turns off the engine, it makes a loud backfire). His girlfriend, Chanice (Madigan), owns a car repair business. They have been together for eight years and she wants him to get a job so they can get married and have a family. Buck accepts a job at Chanice's garage, but is unenthusiastic as he enjoys his freedom. Since no one else is available to help Bob and Cindy, they have no choice but to turn to Buck, who agrees to help. He informs Chanice that he will need to start work later as he tells of the family emergency. Given that Buck has earned a reputation as having a poor work ethic, Chanice thinks Buck is trying, as usual, to lie his way out of working.
Buck quickly befriends Miles and Maizy, but the rebellious Tia is aloof, and the two engage in a battle of wills. When Buck meets Tia's obnoxious boyfriend, Bug (Underwood), he warns her that he is only interested in her for sex. Buck repeatedly thwarts her plans to sneak away on dates with Bug. Over the next several days, he deals with a number of situations in comedic fashion, including taking the kids to his favorite bowling alley, making enormous pancakes for Miles' birthday, ejecting a drunken birthday clown from the property, speaking with the school assistant principal about Maizy, and handling the laundry when the washing machine doesn't work.
When Buck threatens Bug with a hatchet in an attempt to "bury the hatchet" with him, Tia exacts revenge by making Chanice think he is cheating on her with their neighbor, Marcy (Metcalf). One weekend, concerned after Tia sneaks out to a party, he decides to go looking for her rather than attend a horse race which would have provided him with enough money for the entire following year. He calls and begs Chanice to watch Miles and Maizy as he searches for Tia. At the party, thinking that Bug is taking advantage of her in a bedroom, he forces the door open by drilling out the lock, but walks in on Bug with another girl. He ties Bug up and throws him into the trunk of his car. After he finds Tia wandering the streets, she apologizes to him and acknowledges he was right about Bug. Buck lets Bug out of the trunk to apologize to her. When Bug is finally released, he threatens to sue him. Buck then strikes him with a golf ball, making him retract his apology and flee. At home, Tia helps Buck reconcile with Chanice by admitting her lie and tells her that he would be a good husband and father. Buck also agrees to start his job at the garage.
Bob and Cindy return from Indianapolis, Cindy's father having made a recovery. Upon entering the house, Tia hugs her mother which surprises her. Cindy then promises her daughter that things are going to be different from now on. Buck and Chanice then leave for Chicago, with Buck and Tia exchanging a loving wave goodbye.