Playing around while aboard a cruise ship, the Chipmunks and Chipettes accidentally go overboard and end up marooned in a tropical paradise. They discover their new turf is not as deserted as it seems. During a benefit concert in Paris, France, David Seville is injured. Dave must recuperate and is forced to leave his aunt to look after the Chipmunks. Arrangements are also made for them to go to school. After another accident, the Chipmunks are left in the care of Toby, the grandson of Dave’s aunt.
Meanwhile, Ian Hawke lives in the basement of JETT Records. Three singing female chipmunks, Brittany, Jeanette, and Eleanor, also known as the Chipettes, emerge and Ian hires them as plot to get back at the Chipmunks and revive his career.
While at school, the Chipmunks are bullied by jocks and visit the principal’s office. They discover that the principal is a huge fan and wants them to help raise money for the music program by participating in a contest. Meanwhile, when Ian is shocked to find the Chipmunks on the front page of his newspaper. After he reads a story about him, he quickly sends the Chipettes to school.
When the Chipmunks meet the Chipettes, they fall for their counterparts, but are soon forced to have a rivalry after discovering that they are with Ian. Meanwhile Dave finds out Toby is watching the boys, and he quickly leaves the hospital. At the concert, the Chipettes sing and Alvin fails to show for the Chipmunks – who then forfeit. When Alvin finally shows, he finds the auditorium empty and is ignored by his brothers at home.
Soon, the Chipettes are hired. The concert is on the same night as the school contest, so Ian decides to blow off the battle and make the Chipettes perform at the new concert, opening for Britney Spears.
Alvin finds out that Ian has locked the Chipettes in a cage, so Alvin races off to rescue them while Simon tells Jeanette how to open the cage on the phone. The Chipettes manage to escape with Alvin, and they arrive just in time to perform at the contest. The Chipmunks and the Chipettes perform together and they win. Dave returns during the contest. Meanwhile, Ian gets into more trouble at the concert he set up for the girls when he attempts to imitate them. After the contest, Dave allows the Chipettes to stay with them. In a post-credits scene, the principal is making the jocks scrape gum off from under the bleachers in the gyAlvin and the Chipmunks Chipwreckedasium, and Ian ends up in a dumpster.
The vacationing Chipmunks and Chipettes are turning a luxury cruise liner into their personal playground, until they become ‘chipwrecked’ on a remote island. As the ‘Munks and Chipettes try various schemes to find their way home, they accidentally discover their new turf is not as deserted as it seems.

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