Jimmy Harper arrives in Chicago with the Diggs Monroe Jazz Orchestra, where the band hopes to find fame and fortune. Instead Jimmy descends into the jazz underworld where he is introduced to an array of unconventional characters and environs. He becomes entangled in dark dealings with a sinister mob boss and an erortic affair with a black drag performer. In this unfamiliar world, Jimmy begins to question whether he can trust anyone, even his old band members. The trilogy Medicine for the Blues is a work of LGBT historical fiction that explores the complexities of gender and sexuality through the historical lens of the early 1920s. Chicago Blues follows Book 1 Acquaintance. Still to come, Book 3 Dangerous Medicine.