Through all his riverboat experience Armstrong’s musicianship began to mature and expand. At twenty, he could now read music and he started to be featured in extended trumpet solos, one of the first jazzmen to do this, injecting his own personality and style into his solo turns. He had learned how to create a unique sound and also started using singing and patter in his performances. In 1922, Armstrong joined the exodus to Chicago, where he had been invited by his mentor, Joe "King" Oliver, to join his Creole Jazz Band and where he could make a sufficient income so that he no longer needed to supplement his music with day labor jobs. It was a boom time in Chicago and though race relations were poor, the “Windy City” was teeming with jobs for blacks, who were making good wages in factories and had plenty to spend on entertainment.
Oliver's band was the best and most influential hot jazz band in Chicago in the early 1920s, at a time when Chicago was the center of the jazz universe. Armstrong lived like a king in Chicago, in his own apartment with his own private bath (his first). Excited as he was to be in Chicago, he began his career-long pastime of writing nostalgic letters to friends in New Orleans. As Armstrong’s reputation grew, he was challenged to “cutting contests” by hornmen trying to displace the new phenom, who could blow two hundred high C’s in a row.