	On June 17, 2016, Dinwiddie was traded to the Chicago Bulls in exchange for Cameron Bairstow. He was waived by the Bulls on July 7, re-signed on July 28, and waived again on October 21 after appearing in five preseason games. He then spent the start of the 2016–17 season with Chicago's D-League affiliate team, the Windy City Bulls, averaging 19.4 points, 8.1 assists and 3.7 rebounds over 37.4 minutes in nine games.