In the year 1998.
The Chicago Bulls NBA basketball team won their last championship in 1998. They actually won the championship six time in the 1990s. Full statistics of the games can be found on the Chicago Bulls website.
Chicago white sox
At present, their last championship was last 2010
As of 2009 the Chicago White Sox last won the World Series in 2005.
the year 2005
The Chicago Cubs. The Chicago Cubs have not won in 94 years. The last time they won was 1908.
2004 was the last time Connecticut won the NCAA championship
Dec. 14, 1941 - Conference Championship - Chicago 33, Green Bay 14