The right tackle, who was headed toward free agency, has started all 46 regular-season games in which he has appeared over the past three seasons for Chicago, including all 17 games for the Bears in 2018.
"Bobby has been an important part of our offensive line the past three years and has shown steady improvement during that time," Bears general manager Ryan Pace said in a statement. "Bobby has a tremendous work ethic and has displayed the kind of toughness and consistency we want in our players. More importantly, he is a great teammate and we're excited to keep him in the fold."
The offensive line gave up only 33 sacks this season, which was tied for third fewest in the NFC, as the Bears (12-4) won the NFC North in their first season under coach Matt Nagy after four straight last-place finishes.
The 6-foot-6, 315-pound Massie signed with the Bears as a free agent in 2016. He spent his first four NFL seasons with the Arizona Cardinals, who selected him in the fourth round of the 2012 NFL draft.
The Associated Press contributed to this report.