Chicago Cubs last World Series: Then and nowWith the longest championship drought in American professional sports, the Cubs have seen a lot change since they last won the World Series, in 1908.SI Staff|Share on FacebookShare on XAdd us as a preferred sourceWith the longest championship drought in American professional sports, the Cubs have seen a lot change since they last won the World Series, in 1908. Published Oct 4, 2016 | Modified Oct 4, 2016SI STAFFShare on FacebookShare on XHome/MLB