The Raptors, who were ahead by two with 5:22 left, finished the game off on an amazing 20-2 run to finish off the Bulls, and snap a season-high seven-game skid in the process.
Andrea Bargnani added 22 points and five rebounds for Toronto. Chris Bosh finished with 17 points, six rebounds and six steals.
Calderon, who missed 10 of the last 11 games due to a strained right hamstring, went 9-of-10 from the field. He made all four of his foul shots and has connected on his last 83 attempts from the charity stripe. That is now second on the NBA's all-time list, behind only Micheal Williams, who hit 97 straight for Minnesota from March 24 - November 9, 1993.
Ben Gordon paced the Bulls with 19 points. Kirk Hinrich had 17 points for Chicago, which is on a season-high four-game skid. Andres Nocioni scored 15 and Luol Deng had 14 points.
After a back-and-forth first period, the Raptors held onto a 28-25 edge.
Toronto went on a 6-0 run early in the second stanza to take a 34-27 lead. The run was capped off by a Jason Kapono shot from beyond the arc. But the Bulls were quick to fight back with a 7-0 run. A Hinrich three with 8:38 remaining until half tied the contest at 34. Chicago used that momentum to pull away to a slight margin.
The Raptors went on a 6-0 run, topped off by a pair of foul shots from Jermaine O'Neal, late in the second frame to knot the game. The teams went into the locker room tied at 54. Bargnani led all players at the half with 11 points.
Toronto started the third frame on a 13-1 run to gain some breathing room. Calderon made a layup with 8:56 left in the quarter to finish the run. But the Bulls cut the lead to 73-69 with 3:56 to go in the stanza, after a Derrick Rose 20-foot jumper. The Raptors took a 83-74 advantage into the fourth quarter.
Chicago made things interesting by going on a 12-5 run, which was capped off with a Deng 18-foot jumper, to cut the gap to 94-92.