Based on the musical play by Adolph Green, Betty Comden, and Leonard Bernstein, three sailors spend 24 hours romancing three women in New York.
At 6 a.m. sailors Gabey (Gene Kelly), Chip (Frank Sinatra), and Ozzie (Jules Munshin) get liberty for one day. They sing "New York, New York" and see the city. In a subway they see a poster of Ivy Smith (Vera-Ellen) as Miss Turnstiles, and she dances in their imagination. Gabey takes the poster and meets her.
Gabey, Chip, and Ozzie ride in the cab of Hilde (Betty Garrett), and she likes Chip. She drives them to a museum to look for Ivy. Ozzie meets Claire (Ann Miller), who is studying primitive men and kisses him. Claire sings "Prehistoric Man" and tap dances. A dinosaur skeleton collapses, and they run out with her. They try other museums. Hilde suggests they split up, and Chip goes with Hilde to her place. Her roommate Lucy Shmeeler (Alice Pearce) is sick, but Hilde gets her to go out.
Gabey finds Ivy practicing ballet and asks her out. He sings "Main Street" about his home town, and they tap dance. They agree to meet at 8:30. Madame Dilyovska (Florence Bates) reminds Ivy that she has to work at 12.
At eight Chip and Hilde are waiting on top of the Empire State Building. Chip sings "You're Awful." Ozzie and Claire arrive, and Gabey says he found Ivy. The professor and the police look for Ozzie, who hangs over the edge. Ivy arrives, and they sing "On the Town."
Claire and Hilde use cash to get a table and special treatment for Ivy. She has to go at 11:30 and leaves Gabey a note. Hilde calls Lucy for Gabey, who is embarrassed by her. To cheer him up they sing "You Can Count on Me." Gabey takes Lucy home. Gabey imagines a show and dances with Chip, Ozzie, Hilde, and Claire. Then he fantasizes dancing with Ivy.
Gabey sees Madame Dilyovska and learns that Ivy works at Coney Island. Police chase them to Brooklyn. Gabey finds Ivy working as an exotic dancer. She admits she lied and says she is from his home town. They hide in costumes to fool police but are chased into a Shore Patrol van. The three women plead for the sailors and persuade the police to help them. On the dock they kiss goodbye and sing another chorus of "New York, New York."
This musical comedy reflects the build-up of libido in
women during the war that led to the baby boom when the equally
sex-starved men came home. The challenge to establish a romance
in less than one day means that it is mostly based on fantasy.