Mickey and his friends go off on a trip to Orlando to rehearse for their list of new amusement parks, but during the chase, they ends up shipwrecked on the deserted island and is ambushed by the evil tikis.
The film starts where Donald Duck is working on a new song. He plays a few keys to check, but is interrupted by Alvin playing his harmonica. Dave keeps getting interrupted, until he finally yells out "ALVIN!" and Alvin rushes to him with a reply, "OKAY!"
The next day, Donald Duck received a letter from New York City to come and perform at the City Hall. He brings Mickey Mouse and Goofy along with him to do a show. While on their way to New York City in the car, Mickey sings Road Trip to the tune of Bicycle Built for Two. When they finally got to New York City, the people actually came for Daisy Belle's arrival, not the Chipmunks'. Alvin is infuriated with jealousy, but Dave suggests the Chipmunks that they should all be gentleman during their trip. Dave and the boys check into a hotel to stay in for the night. As Dave and The Chipmunks got in, they met up with Sam Valiant again after his last job was a private nose detective. As they went into their rooms after checking in, the boys get ready for bed. As they went to sleep, Alvin dreams about Daisy Belle stealing the show, which causes his popularity to be sunk. When he woke up, Dave tells the boys that they should get ready to rehearse for the list of songs they should sing at City Hall. Dave dials on the telephone for a royal order of room service. The massagers and cooks came into the hotel room to massage the three Chipmunks and Dave Seville. Dave is served bacon and eggs, Simon is served a bagel with strawberry cream on it, Theodore is served hard-boiled eggs, and Alvin is served a large cheese omelette with garlic.
After their nourishment and hearty, healthy breakfast, Dave insists that the boys should rehearse the first song "Christmas, Don't Be Late". When they started rehearsing, they were interrupted by a cat who came in their hotel room window during the middle of rehearsal. Dave wonders what the cat came from. When someone rang the doorbell, Dave comes to check and see who it is. Daisy Belle was at the door, explained why her cat came into the Sevilles' hotel room and asked politely if she could have her cat back. Dave gave the cat back to Daisy Belle. The Chipmunks were shocked that the cat was Daisy Belle's cat after all. Both Simon and Theodore fainted, but Alvin showed some backbone and asks angrily "Your cat?!". Daisy Belle explains to Alvin that unless he is nice to her, she will not let him take care of her cat. She says goodbye to Dave and leaves the hotel room. Alvin is starting to think that women are nothing but trouble, but Dave reminds him about what he told him and his brothers yesterday: to be gentleman. Alvin agrees to the advice in anger and went to his bed. Dave tells Alvin to come out of his bed so that they can continue their rehearsal, and Alvin does so.
Later, the boys take a break from rehearsal of their songs. Stanley the Eagle comes over to visit his friends, The Chipmunks. Alvin asks why he came here to New York City to come over and visit them. Stanley the Eagle explained it all through pantomime, and then gave the Chipmunks a hug. Alvin asks Dave if Stanley could join in their songs. Dave declines and reminds Alvin that eagles can't sing. Alvin points out that Stanley could still make music with them, even though he cannot sing.
At night, The Chipmunks are about to make their appearance on TV. As they got there, Daisy Belle came in first before them since ladies should always go first. Alvin was shocked of when people adored Daisy Belle more than the Chipmunks. Alvin is prepared to get rid of her, but Dave stopped him just in time. He told Alvin that they should be gentleman during their trip and mistreating a lady would be considered the wrong thing to do. Alvin understood Dave and let Daisy Belle have all of the glory. The Chipmunks went back to their limo sadly. Dave was about to get them out to show their faces on TV, but the limo already drove off with them, much to Dave's dismay. Later, The Chipmunks sunk into a deep depression at a local bar drinking root beer and Stanley the Eagle was with them. Alvin tells the group that they are all washed up and that they should give up their music careers. Simon insists that there should be some way to get their fans back, but Alvin replies sadly that things will never be the same. He got on stage and starting singing The Fool with the chorus girls, including Simon and Theodore as backup singers. After the song ends, Simon convinces Alvin that there is still hope for The Chipmunks and that is performing all of their songs on television. Alvin said while looking weary, "You're right, Simon. You're always Simon." Simon replies, "Close enough, Alvin." The three Chipmunks believed in each other and went off happily.
The next morning, Mrs. Frumpington came to visit the Sevilles. She told Dave that there is going to be a singing contest on TV. Dave was thinking of entering the Chipmunks into that contest, and assured her that if the boys win the singing contest, the audience will have the chance to fall in love with the Chipmunks again. Mrs. Frumpington then leaves the room as she said "good bye" to Dave. Dave then tells the boys the news that there is going to be a singing contest and The Chipmunks are very excited about the idea. Dave then tells the boys to practice their songs in their room. Alvin and the others agreed to do so.
As the boys practice their new song, Clyde Crashcup and his faithful lab assistant, Leonardo, dropped by to see the Chipmunks. Crashcup heard about the contest and wondered if he could add special effects to their performance. Alvin and his brothers spoke about it in private, and Alvin told Crashcup that they have agreed with the idea of special effects. Simon and Theodore also knew that they haven't used special effects in their performances, and became interested in it too. Clyde was pleased with their agreement and drew up a new special effects machine that can create effects, such as explosions, dynamite, pyrotechnics, and dust clouds. After he explained it to them, The Chipmunks were pretty hep to the new use of special effects. But Simon stopped for second thoughts on what if Dave would have been very uncooperative with the special effects. Alvin insists that they shall use it in their performances and see how it plays out. Theodore agreed with Alvin. Simon hated to admit it, but that would be a great idea.
At night, the singing contest was in full swing. While Daisy Belle was finishing her song, The Chipmunks are looking out the curtains backstage to see so many contestants. Simon still wondered if Dave wouldn't like their act with special effects, but Clyde told them that he will like it as long as the special effects spice up their songs. Then he told them "good luck" as the Chipmunks went on-stage. The Chipmunks started off with The Chipmunk Song (Christmas Don't Be Late), then Alvin brings out his harmonica as theygo off with the next song, Alvin's Harmonica. As the special effects were in full swing, The Chipmunks do The Alvin Twist and the people joined in on the groove. Then they started to sing My Wild Irish Rose, as Alvin brought out a green-colored rose. Later, the three sing the song Chipmunk Fun while moving and shaking their bodies. Dave was terrified of what would affect with the audience. The Chipmunks then commence with Alvin for President, as Alvin wore a top hat representing the American flag. Then they sang The Little Dog, as they try to find Theodore's dog, until they found him on the bushes. And last but not least, Home on the Range where The Chipmunks are dressed as cowboys. The audience applauded and Dave realized that they actually liked the Chipmunks with their special effects. He then scolds the audience for applauding the show, claiming that the show is an example of pure trash. He seemingly embarrasses the boys, but as Theodore walks off he made a pratfall on stage that everyone sees, and they clap again, completely ignoring Dave, and making the Chipmunks one of the most popular people in New York City. Later, The Chipmunks comes back from a celebration party, but thanks Dave for giving him the chance to express himself and making the show possible. Dave, feeling a bit guilty for the way he acted, admits he was not supportive of the special effects in their performances, and also admits that the show must have been good in the way that people found it entertaining.
The next day, The Chipmunks pack up their things with Dave and said good-bye to New York City. The people in New York City waved goodbye to The Chipmunks as they headed back to their home in Los Angeles, California in the car. As they drove back to their home in Los Angeles, Alvin immediately asks, "Hey, were you there when Theodore made a pratfall?" and the film ends.
In a post-credits scene, Clyde Crashcup is inventing the voice alternator and tests it on Alvin giving him a deeper voice. Alvin told the other kids, "Hey, fellas. What's up?" The other kids thought that Alvin sounded less helium-ish and sounded more like a normal person. Alvin was impressed with Clyde's invention and would treasure it as long as forever. Both Clyde and Alvin hugged each other afterwards.
- Wayne Allwine as Mickey
- Tony Alsemo as Donald
- Bill Farmer as Goofy / Peg Leg Pete
- Russi Taylor as Minnie Mouse
- Tress MacNeille as Daisy Duck / Queen of Hearts
- Jim Cummings as the Native Chief / Big Bad Wolf / Kaa
- Jon Lovitz as Native Goof
- Will Ryan as The Three Natives
- Frank Welker as Cogsnail / Pluto / Seagulls and additional animal sounds
- Corey Burton as Captain Hook / Chernabog / Shere Khan
Disney characters appearing in the film
- Classic Disney Cartoons: Weasels, Lonesome Ghosts, Big Bad Wolf & Three Little Wolves
- Snow White and the Seven Dwarfs: Snow White, Dopey, Bashful, Doc, Sneezy, Happy, Sleepy, and Grumpy, Evil Queen, Old Hag & Raven
- Pinocchio: Pinocchio
- Fantasia: Yen Sid, Chernabog & Faker and Rare
- Bambi: Bambi
- Song of the South: Br'er Rabbit, Br'er Fox & Br'er Bear
- The Adventures of Ichabod and Mr. Toad: Headless Horseman
- Cinderella: Lady Tremaine, Drizella Tremaine & Lucifer
- Alice in Wonderland: Mad Hatter
- Peter Pan: Peter Pan, Tinker Bell, Slightly, Cubby, Mullins, Turk, Danny, Nibs and the Twins, Captain Hook, Mr. Smee, Pirate Crew & Tick-Tock Crocodile
- Sleeping Beauty: Maleficent, Diablo & The Goons
- One Hundred and One Dalmatians: Cruella de Vil & Jasper and Horace
- The Sword in the Stone: Madam Mim
- The Jungle Book: Kaa
- Robin Hood: Prince John, Sir Hiss & Sheriff of Nottingham
- The Rescuers: Madame Medusa & Mr. Snoops
- The Great Mouse Detective: Professor Ratigan & Fidget
The film was released in theaters on July 3, 1987.
- "Road Trip" - Mickey, Donald and Goofy
- "It's a Small World" - Chorus
- "The Natives' March" - The Natives and Chrous
- "Friends for Life" - Mickey, Donald, Goofy and Seagully
The film was released on VHS on September 1, 1998.
In 2002, the film was released on DVD for the first time, to promote the sneak peek of A Very Mouse Movie. The bonus features includes the first episode of House of Mouse, The Stolen Cartoons.
In 2007, the film was released on Blu-Ray for the first time, to promote the film's 20th anniversary.
A sequel, A Very Mouse Movie was released on November 5, 2002.