Solitaire Miles has always loved singing Swing tunes. Her grandmother, a singer with a Big Band in the late 1930s, exposed her to the music as a child. Several members of her family were musicians and she grew up hearing Blues and Jazz at Sunday afternoon family concerts. She performed as a teenager in the late 1980's with well known Jazz saxophonist Bruce Johnstone in the NW Pennsylvania area where she is originally from. Solitaire originally planned to be an opera singer, but while attending DePaul University in Chicago, she met the legendary Swing violinist Johnny Frigo who encouraged her to sing Jazz. After college in the early 1990's she began working in Chicago with Sax Maestro Von Freeman, and pianist Willie Pickens, who also played on her self-titled release in 2006.

"I was lucky to have their guidance because they were playing with the greats in their day.” During the late 90's while living in New York City, she performed with the great trumpeter Doc Cheatham, learning lots more Swing tunes. From these venerable bandleaders, she learned more about phrasing. Since then, she has since been an important part of the Chicago music scene performing with pianist Willie Pickens and leading her own groups.