During the Chipmunks' benefit concert, David Seville (Jason Lee) is badly injured after Alvin jumps onto a scaffolding, and a falling billboard sends him flying across the stage into electric devices. After the accident, he is rushed to the hospital. Although he survives, he must stay to recuperate. He tells Alvin (voiced by Justin Long), Simon (voiced by Matthew Gray Gubler), and Theodore (voiced by Jesse McCartney) that while he is away, he has asked his Aunt Jackie to look after the Chipmunks, and that he has also made arrangements for them to go to school. They head to the airport, where the Chipmunks meet up with Jackie, who introduces her grandson Toby (Zachary Levi) After Aunt Jackie falls down a staircase and a luggage trolley crashes into her, she too is sent to the hospital, leaving Toby in charge.
Meanwhile, Ian Hawke (David Cross), former manager, now lives in the basement of Jett Records. Three singing female chipmunks, Brittany (voiced by Christina Applegate), Jeanette (voiced by Anna Faris), and Eleanor (voiced by Amy Poehler),who call themselves the Chipettes, emerge from a package and introduce themselves to Ian. Brittany says that since Ian made the Chipmunks stars, they want to be stars too. To prove their talent, they sing "Put Your Records On" and Ian hires them.
The tension between Alvin and Simon builds as Alvin hangs out with the jocks of the school, but the one who is most affected is Theodore who believes he is losing his brothers because they are fighting all the time.
The Chipmunks meet the Chipettes and gains crushes for their counterparts, but are soon forced to have a rivalry after discovering that they are with Ian. The Chipmunks and the Chipettes compete against each other in a Battle of the Bands. During lunchtime, Alvin meets up with Brittany, sharing a slightly romantic moment with her until he warns her about what Ian did to him and his brothers, but Brittany does not believe him. At the concert, the Chipettes sing "Single Ladies (Put a Ring on It)". Ian videotapes the Chipettes performance and posts it on YouTube, along with his phone number. The Chipettes win the competition and Ian became rich and famous again after Simon and Theodore forfeit the competition because Alvin failed to show up. Alvin later shows up only to see that everyone's gone. When Alvin returns home, Simon and Theodore pretend they're sleeping and ignore him. The embarrassment is too much for Theodore to take so he runs away to the zoo. When Toby and the boys find him and save him from an eagle, it brings out the best in all four of them and the Chipmunks all forgive each other and go back to "One for all, and three for one," as Theodore had said.
Soon, the Chipettes are hired as the opening act at a Britney Spears concert at the Staples Center. Unfortunately, the concert is on the same night as the school concert, so Ian decides to blow off the battle and make the Chipettes perform at the concert. However, since he focuses on Brittany the most, he wants her to perform onstage alone while Jeanette and Eleanor sing backup. Brittany refuses to sing without her sisters, so Ian threatens to send them to a barbecue restaurant if they refuse and was kidnapped by Ian after they realized that Ian just use them to become rich.
At the school, Toby gets a phone call from Ian, and Alvin answers it, but he learns that it's from Brittany, saying that she and her sisters have been locked in a cage. Alvin is able to free the girls from Ian and are able to get away and head back top the school. Simon and Theodore are about to forfeit the concert again, but Toby tries to stall the crowd. Alvin and the Chipettes fly into the hall on the helicopter and they all sing "We Are Family". Dave then arrives and watches them perform.
The Chipettes are adopted at the boys' request and sleep at the Chipmunks' house where Dave wishes them good night, but Alvin refuses to go to sleep. So, while Dave turns off the lights, Alvin turns them back on. Dave eventually gets irritated, and goes over to Alvin, who turns off the lights, causing Dave to trip over a skateboard. "Exhausted," Alvin turns on the lights, and wishes Dave good-night, turns off the lights, and the movie ends with Dave yelling "ALVIN!"
In an epilogue, the jocks are shown cleaning gun off the bleachers while Dr. Rubun watches over them.
In the post-credits, Ian is shown being thrown into a dumpster backstage by the guards. (http://en.wikipedia.org/wiki/Alvin_and_the_Chipmunks:_The_Squeakquel)
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