Chicago Sports: Five greatest moments since 1990

(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images) /
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Chicago Blackhawks Patrick Kane
(Photo credit should read JEFF HAYNES/AFP via Getty Images) /

Super Bowl XLI

As mentioned before, the Chicago Bears are the only team in Chicago that didn’t win their championship during the window of 1990-2020. They did, however, reach the Super Bowl in 2007 following the 2006 season. That is easily their greatest accomplishment during the time frame. They did end up losing the big game to Peyton Manning‘s Indianapolis Colts by a final score of 29-17. It was a bitter end to an otherwise sweet season.

The got to the Super Bowl by defeating the New Orleans Saints in the NFC Championship Game by a final score of 39-14. On the first play of the Super Bowl, Chicago Bears star Devin Hester returned the opening kickoff for a touchdown. That came after a rookie season that saw him make a name for himself as the best kick returner in the game. He was the first player in Super Bowl history to return the game’s opening kick for a touchdown.

Even though it ended in a loss, the Bears are the most popular team in Chicago so just reaching the Super Bowl will go down as an all-time great Chicago sports moment. Peyton Manning was a respected opponent and he simply got the best of that Bears team. Players like Brian Urlacher, Lance Briggs, and Charles Tillman were the key cogs to elite defense and quarterback Rex Grossman played just well enough to get them to where they needed to be.

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The Bears seemed to be on the right track after the 2018 season but the 2019 season was a major disappointment. The fact that losing the Super Bowl was one of the most memorable moments in Chicago sports history tells you everything you need to know about what it would be like if they actually ever won it.