The Bears have made the playoffs 24 times.
2
30 playoff appearances in 49 years....
Once - in the 1999 season, vs. the St. Louis Rams.
The New York Yankees with 47.
The New York Jets have made 13 playoff appearances.
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.
No. Never even made it to the finals. 4 playoff appearances.
The Chicago Bears Hat was made officialy in 2010. It was made in the year of the Chigago Bears finnaly winning a score in the playoffs. There aren't too many fans of this hat.
The 2009 season is the 8th consecutive season the Colts have made the playoffs. They last missed the playoffs in 2001.
The Seattle Mariners have been in the Major Leagues since 1977 (33 years) and have never been in the World Series. If you're asking about the longest drought of a team who HAS been in a World Series before but hasn't been in one since, the Chicago Cubs were last in the World Series in 1945, but haven't been in one since, making that a 65 year stint.
2007