He began in Zack Whyte's band in 1928. In his early days he worked with Ethel Waters, Adelaide Hall, and Clarence Williams. In the mid-1930s he was associated with Willie Lewis's band and toured Europe with them. Later he and Bill Coleman led the "Harlem Rhythm makers". Chittison was one of the earliest and most important ambassadors of American jazz in Europe. As it is shown by many of his early recordings of 1933-1941, he was also a formidable virtuoso, with a piano technique very close to Art Tatum's.
The radio program Casey, Crime Photographer featured Chittison playing jazz piano at the Blue Note Club, Casey's informal headquarters. A later series of the same show featured the Teddy Wilson Trio in the same setting.