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.