Life R. Kelly: Chicago judge sets tentative trial date for September 2020, pushes for progress December 4, 2019 Maria Puente, USA TODAY Comments Off on R. Kelly: Chicago judge sets tentative trial date for September 2020, pushes for progress Facing multiple sex-crime charges, R. Kelly could be tried in three courts in two states in a six-month period of 2020, if tentative trial dates hold.