Chicago has made two Super Bowl appearances since the inception of the title game in 1966, winning on their first trip in 1985. Prior to the SuperBowl era, the Bears won 8 NFL championship games in 11 post-season appearances.
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The Chicago Bears have been to the NFL playoffs 24 times. They have won their conference championship 3 times (1963, 1985, 2007). They have only won the Super Bowl once though, in 1985.
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The past 30 years would be from the 1980 season. The Steelers made the playoffs 17 times since 1980.
15 times
The Boston Red Sox have been in the playoffs 20 times since 1901(when baseball started having leagues and championships).
after the 2003-04 season the Flyers have made the playoffs 30 out of 37 seasons. they missed the playoffs 1969-70, 1971-72 and from 1989-90 thru to 1993-94