The Mother of the Blues, Ma Rainey, 1927, Chicago.
Although not from Chicago, Ma Rainey was discovered by Chicago-based Paramount Records. She would go on to record the lion’s share of her greatest recordings while calling the city her home-away-from-home.
Do yourself a favor and search for her online recordings. From her not-so-subtle references to sex and other scandalous subjects (like her own proclivity for sleeping with women), her music is like no other.