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.
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)