Chicago’s Best Sports Night: Bears Comeback, Bregman to Cubs Deal.

Sporting successes have not been a regular occurrence for the city of Chicago.

The metropolis has faced a challenging period over the past five years or so, experiencing a restructuring of the Bears, the Cubs’ difficulty in achieving significant progress, the Blackhawks’ absence from the playoffs since the 2019-20 season, and the continued ownership of both the Bulls and White Sox by Jerry Reinsdorf.

However, Saturday brought a spark of optimism, with three triumphs for the Windy City, featuring a dramatic playoff comeback against an opponent, and the area’s most significant Major League Baseball acquisition in quite some time.

The standout achievement was the Bears’ victory at home against the Green Bay Packers during the NFL wild-card stage. Trailing 21-6 entering the final quarter, Caleb Williams and his teammates scored 25 points in the fourth, securing a 31-27 win and shocking a rival that has dominated them historically for around the last thirty years.

This victory solidified the Bears’ excellent regular season performance, as they surpassed the Packers to claim their initial NFC North title since the 2018 campaign. The Bears achieved an 11-6 record under first-year head coach Ben Johnson, demonstrating a propensity for exciting finishes throughout the season, but elevated their game even further in their inaugural playoff contest.

Chicago Bears' Caleb Williams celebrates after an NFL wild-card playoff football game against the Green Bay Packers Saturday, Jan. 10, 2026, in Chicago. (AP Photo/Erin Hooley)

The city of Chicago has long anticipated a day such as Saturday. (AP Photo/Erin Hooley)

(ASSOCIATED PRESS)

Within professional baseball, the Cubs’ signing of free-agent third baseman Alex Bregman to a five-year, $175 million agreement brought joy to the North Side team. This contract represents the third-largest in the team’s history by total value and the most significant ever in terms of average annual value.

This acquisition provides the Cubs with a high-impact player at third base, skilled in both offense and defense. While the long-term success of the agreement remains to be seen, it establishes the squad as the frontrunner in the NL Central according to BetMGM, which presently offers them +150 odds to overtake the Milwaukee Brewers.

News of the Bregman agreement emerged during the early part of the fourth quarter of the Packers-Bears matchup.

On Saturday, the Bulls decisively defeated a Dallas Mavericks squad that was without Anthony Davis; seven distinct players achieved double-digit scoring, with Coby White topping the chart with 22 points. Chicago maintained a lead of ten points or more throughout the entire final quarter.

Regarding the Blackhawks, they secured their initial win since Connor Bedard’s return. The exceptional player, having been sidelined for 12 games due to a shoulder ailment, contributed two assists to their 3-0 triumph against the Nashville Predators.

As for the White Sox, thankfully, their situation did not deteriorate. Their major offseason actions include the two-year, $34 million contract secured with Japanese sensation Munetaka Murakami in December, and winning the 2026 MLB Draft lottery. Moreover, they continue to have the spiritual support of the Pope.

Admittedly, none of Chicago’s teams claimed a championship on Saturday. The Bears require three more victories to secure the Lombardi Trophy, and neither the Bulls nor the Blackhawks are considered championship contenders this current season. The Cubs certainly possess enhanced talent presently, yet their path to a World Series title remains extensive.

Nevertheless, the day was positive.