Come Fly With Me is an album by American singer Frank Sinatra, released in 1958 .

Sinatra's first collaboration with arranger/conductor Billy May, Come Fly With Me was designed as a musical trip around the world. Sammy Cahn and Jimmy Van Heusen wrote the title track at Sinatra's request .

In his autobiography All You Need is Ears, famed producer George Martin writes of having visited the Capitol Tower during the recording sessions for the album. According to Martin's book, Sinatra expressed intense dislike for the album cover upon being first shown a mock-up, suggesting it looked like an advertisement for TWA.

The album reached #1 on the Billboard album chart in its second week, and remained at the top for five weeks. At the Grammy Awards of 1959 Come Fly with Me was nominated for the Grammy Award for Album of the Year.

Though recorded in true stereo, "Come Fly With Me" was released to record stores in 1958 in monaural only; a standard practice by Capitol records at the time. The label finally released the stereo version in 1962. The differences between the 1958 monaural and subsequent 1962 stereo recording of "Come Fly With Me" are striking. The 1958 mono recording contains a depth and warmth, most especially in specific string and brass sections, which is lacking in the stereo remix of the album relased by Capitol as SW-920 in 1962. The original mono recording from 1958 is now all but lost to history, except for original Grey Capitol Label copies, labeled W-920, and some CD compilations. Capitol CD and remastered series (1992 and 1998 respectively) reproduce only the 1962 stereo version.