2008 but hopefully they will make it in the 2012 season
Through the 2008 season, the last season both the Cubs and White Sox were in the MLB playoffs was 1906. The White Sox defeated the Cubs, 4 games to 2, in the World Series. This is the only season both Chicago teams made the MLB playoffs in the same season.
Chicago Cubs
The Chicago Cubs won the World Series was in 1908. That is over 100 years ago!
As of the 2007 playoffs, no. The Chicago Cubs have not won a World Series since 1908. The Indians have the second longest drought in MLB having last won the World Series in 1948.
2007
The Chicago Cubs never won a world seires, but the played in the world series when Eriene Banks was on the cubs (lost to the Red Sox)
1908
The last time the Chicago Cubs won the World Series was in 1908.
National League: Chicago Cubs, last World Series in 1945. American League: Cleveland Indians, last World Series in 1954.
1910
In 1908.