On March 14, 2018, Parkey signed a four-year contract with the Chicago Bears.
On November 11, 2018, against the Detroit Lions, Parkey had four kicks (two extra points and two field goals) strike the uprights; none went through. Despite his misses, the Bears won 34–22. In Week 11 against the Minnesota Vikings, Parkey made three field goals in the 25–20 win. He was named the NFC Special Teams Player of the Week for his performance. Parkey ended the regular season having made 23 of 30 field goal attempts.