On May 9, 2008, the Padres released him after hitting only .178 with one home run in 90 at bats. On May 14, 2008, the Chicago Cubs, in need of a left-handed bat, signed Edmonds to a one-year contract of which the Cubs were only responsible for the league minimum. He started the next day against his former team, the Padres, and went 1 for 4. Edmonds was not well received initially by the fans in Chicago, but after joining the Cubs, he hit over .300 with 8 home runs in his first six weeks. On June 21, 2008, Edmonds hit two home runs in the fourth inning against the Chicago White Sox. He also had two other multi-homer games as a Cub: one on July 31, 2008 against the Milwaukee Brewers and one on August 8, 2008 against his former team, the St. Louis Cardinals.