For the second straight week, it looked as if veteran safety Charles Woodson would be the hero for the Raiders.
After making a late interception a week earlier to preserve a victory in Cleveland, Woodson again came up with a fourth-quarter pick to kill a Bears drive and allow the Raiders to make a long drive for a go-ahead field goal.
It was the 62nd career interception for Woodson, who just recently turned 39.
Sebastian Janikowski’s 41-yard kick with 2:10 remaining gave Oakland a 20-19 lead.
But this time, the Raiders’ defense folded in the clutch.
Bears quarterback Jay Cutler drove his team from its own 20 to the Raiders’ 32 with seven seconds left, from where Robbie Gould connected on a 50-yarder to give Chicago a 22-20 victory.
The big play came on fourth-and-5 from Chicago’s own 25, when Cutler connected with tight end Martellus Bennett for 7 yards.
The Bears – who entered the game winless and as underdogs – walked away with their first win of 2015.
Instead of being 3-1 heading into a showdown with AFC West rival Denver next week, the Raiders will have to settle for being 2-2.
The loss was a disappointment for an Oakland team that again produced offensively, yet fell short of winning consecutive road games for the first time since 2011.
Quarterback Derek Carr completed 20-of-33 throws for 196 yards and two touchdowns, with nine of those receptions picked by the combination of Michael Crabtree and Amari Cooper. Cooper and running back Roy Helu Jr. both scored TDs for Oakland.