stylistic:tone, quality:correction, information:highlighting
Chicago period recordings

In 1922, Armstrong moved to Chicago at the invitation of King Oliver, although Armstrong would return to New Orleans periodically for the rest of his life. Playing second cornet to Oliver in Oliver's Creole Jazz Band in the black-only Lincoln Gardens on the South Side of Chicago, Armstrong could make enough money to quit his day jobs. Although race relations were poor, Chicago was booming. The city had jobs for blacks, who made good wages at factories, with some left for entertainment.

Oliver's band was among Chicago's most influential jazz bands in the early 1920s. Armstrong lived luxuriously in his apartment with his first private bath. Excited to be in Chicago, Armstrong began his career-long pastime of writing letters to friends in New Orleans. Armstrong could blow 200 high Cs in a row. As his reputation grew, Armstrong was challenged to cutting contests by other musicians.

Armstrong's first studio recordings were with Oliver for Gennett Records on April 5 – 6, 1923. They endured several hours on the train to remote Richmond, Indiana, and the band was paid little. The quality of the performances was affected by a lack of rehearsal, crude recording equipment, bad acoustics, and a cramped studio. These early recordings were true acoustic, the band playing directly into a large funnel connected directly to the needle making the groove in the master recording. The much improved Electrical recording system with a better dynamic range was not invented until 1926. Initially, because Armstrong's playing was so loud, Oliver could not be heard on the recording when he played next to Oliver. Armstrong had to stand 15 feet from Oliver in a far corner of the room to remedy this.

Lil Hardin, whom Armstrong would marry in 1924, urged Armstrong to seek more prominent billing and develop his style apart from the influence of Oliver. At her suggestion, Armstrong began playing classical music in church concerts to broaden his skills and dressing more stylishly to offset his girth. Her influence eventually undermined Armstrong's relationship with his mentor, especially concerning his salary and additional money that Oliver held back from Armstrong and other band members. Armstrong's mother, May Ann Albert, came to visit him in Chicago during the summer of 1923 after being told that Armstrong was "out of work, out of money, hungry, and sick"; Hardin located and decorated an apartment for her to live in while she stayed.