Chicago Bulls (2016-2018) Edit
On June 22, 2016, Grant was traded, along with José Calderón and Robin Lopez, to the Chicago Bulls in exchange for Derrick Rose, future teammate Justin Holiday and a 2017 second-round draft pick. The following month, he helped the Bulls win the Las Vegas Summer League championship game and earned MVP honors for his 24 points, 10 rebounds, and five assists. On November 15, 2016, he made his first start of the season and had 18 points and five steals in a 113–88 win over the Portland Trail Blazers. On November 26, he was assigned to the Windy City Bulls, Chicago's D-League affiliate. He was recalled on November 27, reassigned on December 9, and recalled again on December 10. On April 10, 2017, he had 17 points and a career-high 11 assists in a 122–75 win over the Orlando Magic.
On November 26, 2017, Grant scored a career-high 24 points in a 100–93 loss to the Miami Heat. On December 29, 2017, he had 11 points, 12 assists and seven rebounds as a starter in a 119–107 win over the Indiana Pacers. On January 22, 2018, he had 22 points and 13 assists in a 132–128 double overtime loss to the New Orleans Pelicans.
Orlando Magic (2018–2019) Edit
On July 7, 2018, Grant was traded to the Orlando Magic in a three-team deal. On June 30, 2019, Grant did not receive a qualifying offer from the Magic, making him an unrestricted free agent