Strike Up the Band (1940)

Jimmy Connors and his girlfriend want to take part in Paul Whiteman's high school bands contest, but they cannot afford the fare. But per chance they meet Paul Whiteman in person and are able to convince him that their band is good enough, so he lends them the money.

But then one of their friends becomes seriously ill and has to be carried to a hospital by plane, and they have to use Whiteman's money for this.