On August 1, 2016, the Angels traded Smith to the Chicago Cubs for prospect Jesus Castillo. In 16 more appearances with the Cubs to finish 2016, Smith had a 1-1 record and a 2.51 ERA. Overall in 2016, combined with both teams he played for, Smith made 54 total appearances with a 1-4 record and a 3.82 ERA. Smith was a member of the Cubs' 2016 World Series championship team, but did not make any postseason appearances.