The Chicago Cubs have won 2 World Series Championships - 1907 and 1908.
In 1906 the Cubs won a MLB record 116 regular season games but lost the World Series to their cross-town rivals, the mighty White Sox.
The Cubs are currently in the midst of 102 year title drought. They haven't appeared in a World Series since 1945.
Since 1876 the Cubs have won 16 N.L. Pennants. 5 divisional titles (2 east and 3 central) However, they have only won 2 World Series Championships, their last one coming 102 years ago in 1908. This is the longest Championship drought by an individual franchise in all of sports. The Cubs haven't appeared in a World Series since 1945.
In 1906 the Cubs won an MLB record 116 regular season games making them heavy favorites for that seasons World Championship. However, they lost 4 games to 2 to the Chicago White Sox, the Cubs rivals from Chicago's South Side.
The White Sox brought home Chicago's first World Series title (1906) and its last (2005)
Major league titles World Series titles (2) 1908 • 1907
NL Pennants (16) 1945 • 1938 • 1935 • 1932
1929 • 1918 • 1910 • 1908
1907 • 1906 • 1886 • 1885
1882 • 1881 • 1880 • 1876
Central Division titles (2) 2007 • 2003
East Division titles (2) 1989 • 1984
Wild card berths (1) 1998
The Bears won 6 NFL Championships prior to the first Super Bowl.
The Stanleys (now the bears) won 1 and lost 1
One
4 championships
22
2 championships 1997 & 1998
1
2 championships - 2001 and 2002
4 championships.
2
5 time
Only once, in 1985, but they have won a number of NFL Championships (before the Super Bowl)