An aspiring actress, Ramona Larosa, enjoys special treatment from her "sugar daddy," Victor Hamilton. Her second cousin, Kent Stevenson, and friend, Jasmin Clark accompany her on many air shows and fun evenings at Chicago speakeasies, movies, and Victor's parties. Along the way, they encounter many different 1920s celebrities such as jazz cornetist Bix Beiderbecke, Louis Armstrong, and Hoagy Carmichael. Ramona gets entangled in a love triangle with barnstormer pilot, Doug Rayburn. After a plane crash, Doug decides to enter the Pulitzer Prize race to be held in Dayton, Ohio. Ramona tries to balance her time between the two lovers, and even manages to get Victor to loan Doug the money he needs for a racing plane.