Outlaw was 9-of-14 from the floor, including four three-pointers, and hit 11-of-13 at the line as Portland kicked off a four-game road trip with its third straight win.
Greg Oden checked in with 17 points and 13 rebounds in an off-night for guard Brandon Roy, who was 3-of-13 shooting for 11 points. Roy did have eight rebounds in his second game back from a four-game absence due to a sore hamstring.
Steve Blake added 16 points and 10 assists to the cause.
Drew Gooden led the way with 22 points and nine rebounds for the Bulls, who concluded a five-game homestand 2-3 and dropped their home mark to 12-7 this season.
Ben Gordon had 17 points and Derrick Rose collected 13 points and 10 assists in a losing effort.
Chicago guard Kirk Hinrich returned to the hardwood on Monday, two months removed from having surgery on his right thumb. He suffered a torn ulnar collateral ligament in the third quarter of a November 7 contest against Phoenix. He had surgery four days later and was expected to be sidelined up to three months.
Luol Deng, who missed the past eight games with a sprained left ankle, also returned to the lineup but it wasn't enough as the floor time for both players was limited with Hinrich chipping in four points and Deng 14 on 3-of-10 shooting.
Down by 11 to start the fourth, Chicago trimmed its deficit to five on a Rose free throw with eight minutes remaining. The Blazers, though, got threes from Blake, Roy and Rudy Fernandez as part of an 11-0 response that opened a 16- point lead with a little over six minutes to play and Portland held a double- digit lead the rest of the way.
The Bulls opened a 28-21 lead after 12 minutes, but the Blazers mounted a surge through the latter stages of the second, sparked by Oden's 10 points in the frame. Portland closed the half on a 14-3 run, bookended by threes from Blake and Outlaw to gain a three-point edge, 49-45.
Three-pointers from Blake and Nicolas Batum early in the third helped the Blazers establish an 11-point advantage and a pair of free throws from Bayless to cap the frame afforded for the same margin, 77-66, entering the fourth.