On May 6, 2019, Pineiro was traded to the Chicago Bears in exchange for a conditional seventh-round pick in the 2021 NFL Draft, and he was one of nine participants in the Bears' 2019 summer kicking competition to replace Cody Parkey. The tryout was orchestrated by coach Matt Nagy to find a new kicker in the wake of the Bears' "Double-Doink" loss against the Philadelphia Eagles in the playoffs, when Parkey missed the game-winning field goal. Eddy had a pretty solid year in Chicago and he made some crucial kicks in big moments.
He then missed the entire 2020 season due to a groin injury. Unfortunately, he did not play again for the Bears.
In 2021, he spent time with the Colts, the Washington Football Team and also the Jets. He started 5 games for the Jets and he was perfect on his field goals attempts while hitting 90% of his extra points.
Here is a throwback to his 53-yard walk-off game-winning field goal: