Hill was born in Charleston, South Carolina, one of sixteen children. The family moved to New York in 1915. She began her career as a dancer in Harlem and by 1919 was working with Ethel Waters. At age 14, during a stint at Leroy's, a noted New York nightclub, Hill was nicknamed "Chippie" because of her youth. She also performed with Ma Rainey as part of the Rabbit Foot Minstrels. She later established her own song and dance act and toured on the TOBA circuit in the early 1920s.
About 1925, she settled in Chicago, where she worked at various venues with King Oliver's Jazz Band. She first recorded in November 1925 for Okeh Records, backed by the cornet player Louis Armstrong and the pianist Richard M. Jones, singing such songs as "Pratt City Blues", "Low Land Blues" and "Kid Man Blues" that year and "Georgia Man" and "Trouble in Mind" with the same musicians in 1926.
