Will the Chicago Bears ever win another Super Bowl?

They might win another one, but not for another few years.

This year ...it's happening this year.

That's what I said last year, and the year before, and before that... etc, etc

Probably not while the McCaskeys still own the team.  

They have already won a Super Bowl before.

Hell yeah to windy city. 

Yes, all it takes is one good year. Just look at the Tampa Bay Buccaneers, a historically losing franchise. They caught lightning in a bottle twice, and won 2 Super Bowl Championships in 20 years. That can happen to the Bears or any other team (yes, even the Detroit Lions). The Chicago Bears were close in 2006 and 2010, and those near misses prove that the Bears can win a Super Bowl.

Keep in mind, winning a Super Bowl is about getting hot at the right time and requires a little luck. If a few things go different in 2010 (say the Buccaneers held on against the Lions, and the Packers miss the playoffs), the Bears might have been the ones to beat the Steelers in Super Bowl XLV.