Three chipmunk brothers, Alvin, Simon, and Theodore are adopted by human, Dave.
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After Alvin, Simon and Theodore use Dave's antique gold pocket watch for Show & Tell at school, neighborhood bullies steal it. The Chipmunks find Mr.T to ask him for some advice and with his help they manage to get the watch back.
For the first time The Chipmunks meet their female counterparts, The Chipettes: Brittany, Jeanette and Eleanor.
A charaltan chipmunk named Harry claims to be Alvin, Simon and Theodore's long lost uncle and says he will have them see their mother as soon as they make enough money. The Chipmunks later not only find out that Harry is not their uncle but also the money he has them making is for a carnival strongman who he has owed for a long time.
The Chipmunks create a robot out of Alvin's video game, so that it can carry all of their equipment to their concerts. But, the robot goes beserk when it begins to capture every hat it sees, like the video game, it was created from, and It's up to Alvin, Simon, and Theodore to stop the robot.
Alvin tells a girl he wants to impress that they are famous and that they are going to be starring in a rock concert on live t.v., but Alvin must convince the producer to let him play.
Alvin unknowingly assists a jewel thief steal some jewelry from a cabin on their cruise ship, and Simon and Theodore begin to investigate the crime.