In diesem Animationsfilm treffen Alvin und die Chipmunks zum ersten Mal ihren zukünftigen Manager – den erfolglosen Liedermacher David „Dave“ Seville.

Alvin, Simon, Theodore und ihr gestresster Manager Dave sind wieder da. Doch diesmal haben sie Konkurrenz: die Chipettes.

In dieser Fortsetzung will das pelzige Trio Alvin, Simon und Theodore bei einer Reise quer durchs Land Dave davon abhalten, seiner Freundin einen Heiratsantrag zu machen.

Alvin und die Chipmunks lassen es sich an Bord eines Kreuzfahrtschiffs gut gehen. Ohne Ärger geht es auch hier nicht … und sie stranden prompt auf einer einsamen Insel.

As Alvin struggles with nightmares involving werewolves, the school play of Jekyll & Hyde is in jeopardy when the lead, Alvin, is suspended. In an attempt to boost his confidence, the principal suggests Theodore, who's suddenly going through some canine changes.

The Chipmunks work in an amusement park attraction. After Alvin drives a crazy tour group, they miss their next performance and are locked in the park after closing time. Little do they know that the real Dr. Frankenstein has been hired in a new attraction called, "Frankenstein's Castle"; figuring that the castle isn't scary enough, the mad scientist recreates the real Monster.

The Chipmunks and the Chipettes go head to head in a hot air balloon race, and the winner gets $10,000. Unbeknownst to the participants, the "race" is actually a diamond smuggling ring!

Alvin learns the true meaning of Christmas.

A live-action/animated TV special featuring Alvin and the Chipmunks.

When he hears that the original Easter Bunny was not a rabbit at all, Alvin becomes convinced that the first deliverer of Easter baskets was indeed his grandfather, the Easter Chipmunk.

The Chipmunks are discussing when they were born and began to argue. They wanted to go and find their mother but Dave doesn't let them. The Chipettes are invited round while the Chipmunks go and look for their mother but Dave finds out and gets worried...

Thanksgiving Day is on the way.

Alvin, Simon, and Theodore finish making invitations to send to their relatives and then leave to audition for the town play "Pilgrims Adventures in a New Land". Alvin trys for the role of the Lead, while Simon trys for Lighting and Sound director, and Theodore Costume Designer. However, the Director of the play feels that to properly celebrate the pilgrims story of adventure, the boys should branch out and attempt new positions. As a result, she casts Simon as the Lead, Theodore as Lighting and Sound Director, and Alvin as the Costume Designer to expand their talents.