Hebner remained in a part-time role with the Pirates through the 1983 season. After which, he signed with the Chicago Cubs as a free agent. Used primarily as a pinch hitter, and occasionally filling in at first and third, he played a valuable role for the team that reached the postseason for the first time since 1945. He returned to that role with the Cubs in 1985, and was among the league leaders in pinch hits before ending the season in an 0 for 22 slump. He still led the majors with twelve pinch-hit RBIs.