The heartbreak never seems to end for Chicago sports; perhaps this is the price they must pay for having the most dominant run in the NBA in recent memory, with the Chicago Bulls winning six titles in an eight-year span. With the Chicago Bears recently being eliminated from Super Bowl contention with a heartbreaking 20-17 loss to the Los Angeles Rams in overtime on Sunday night, QB Caleb Williams visited the Chicago Blackhawks at United Center during their Monday night clash against the Winnipeg Jets.
Williams wasn’t alone, however. He pulled up to the game and was in attendance alongside another current Chicago sporting star in Chicago Cubs centerfielder Pete Crow-Armstrong, who had an excellent 2025 season for the 92-win team that ended up falling short to the Milwaukee Brewers in the NLDS.
CHICAGO IS ROCKING TONIGHT!!!@ChicagoBears quarterback Caleb Williams and @Cubs outfielder Pete Crow-Armstrong are taking in the action at United Center
pic.twitter.com/84yQugmoVT
— NHL (@NHL) January 20, 2026
It remains to be seen if Williams and Crow-Armstrong’s presence for the Blackhawks’ intra-division clash against the Jets would have a positive influence on the team.
But the Jets are the rare team with a worse record than the Blackhawks do this season (only the Jets and Vancouver Canucks have been worse than Chicago this year), so this at least represents a good opportunity for Chicago’s NHL team to get back to winning ways.
Bears and Cubs typify Chicago’s sporting heartbreak
The city of Chicago has not known this much hope in the NFL for over a decade; they haven’t made it past the Wild Card round since 2010. But the Bears, despite receiving a first-round bye, fell short in the most crucial moment to the Rams in overtime.
Meanwhile, the Cubs made it to the playoffs as a team with real contending aspirations but ran into one of the hottest teams in MLB in the Brewers.
As for the Blackhawks, they haven’t been good this decade (they haven’t recorded a season with over 68 points since 2020). The Bulls’ last season as a true contending team came in 2015. Let’s not even get started on the Chicago White Sox.
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