Once, in Super Bowl XX.
(1) once 1985 Bears
One, in 1985.
Just once - 1985.
Twice (1986 and 2007).
The Bears have been to the Super Bowl twice. The 85 Bears, (played in Super Bowl 20 on Jan 26, 1986) beating the New England Patriots 46-10 and the 2006 Bears, (played in Super Bowl 41 on Feb 4, 2007) losing to the Indianapolis Colts 29-17.
The Chicago Bears have lost 1 Super Bowl in 2007 to the Indianapolis Colts. The Chicago Bears have won 1 Super Bowl also in 1986.
They've only lost the Super Bowl one time when they lost to the Indianopolis Colts 29-17.
They have made the playoffs 25 times with a record of 17-18.