1906. However, they wet the bed in the World Series that year against their cross-town rivals, the White Sox, losing the 1906 series 4 games to 2 and thus making the White Sox the First Chicago team to win a World Series Championship. Interestingly enough, the White Sox are the last team to have won a World Series championship in Chicago (2005) as well. The White Sox put up one of the most dominating playoff performances in ALL of MLB history going 11-1 in 2005 after going wire to wire in first place during the regular season.
The Chicago Cubs are in the midst of a 102 year World Series Championship drought. The haven't made a World Series appearance since 1945. This is the longest championship drought in all of professional sports.
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As of the 2008 season, the Cubs have won 100+ games in a season 5 times: 1906: 116-36
1907: 107-45
1909: 104-49
1910: 104-50
1935: 100-54 Through games of August 28 in the 2008 season, the Cubs record is 84-50. They need to play the final 28 games of the season at 16-12 or better to make 2008 their 6th 100+ win season.