The Chicago Bears just won their first playoff game in 15 years.
Now one NFL analyst believes the team is about to take an even bigger leap—and he says bettors should already be paying attention.

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NFL Analyst Predicts Caleb Williams and Bears Will Easily Surpass 9 Wins in 2026

The Chicago Bears are entering the 2026 season with something they haven’t had in years: genuine momentum.

After breaking through with their first playoff victory in 15 years, optimism around the franchise has exploded. With Caleb Williams emerging as a franchise quarterback and Ben Johnson reshaping the offense, many analysts believe Chicago could be poised for another big season.

Yet sportsbooks are setting the Bears’ projected win total at 9.5 games.

According to prominent NFL analyst Colin Cowherd, that number might be far too low.

In fact, he believes betting the over could be one of the easiest wagers of the offseason.

Why the Bears Are Generating Buzz

Chicago finished the 2025 season with an impressive 11–6 record, the team’s best performance since 2018.

More importantly, the Bears finally showed signs of building something sustainable.

Williams took a major leap in his second season, while Johnson’s offensive system helped transform the team into one of the NFL’s most productive units.

Last season, Chicago ranked:

• Top 10 in points per game
• Top 5 in total yards per game
• 44% third-down conversion rate

Those numbers reflect an offense that consistently moved the ball and controlled games.

For a team led by a young quarterback still developing, that level of efficiency has analysts excited about what could come next.

Key Offseason Additions

Cowherd also pointed to Chicago’s offseason moves as another reason for optimism.

The Bears strengthened several areas of the roster by adding experienced contributors, including:

• Coby Bryant
• Devin Bush
• Garrett Bradbury

Combined with the continued development of the team’s young stars, the roster appears deeper and more balanced heading into the new season.

Williams himself is expected to take another step forward in his third year in the NFL.

A Favorable Schedule Ahead

Another factor boosting expectations is Chicago’s upcoming schedule.

The Bears are set to face teams from the NFC South and the AFC East, divisions that could present several favorable matchups.

Cowherd specifically pointed to games against teams like the New York Jets and Miami Dolphins as winnable opportunities.

If Chicago capitalizes on those matchups, reaching double-digit wins could become a realistic goal.

Reasons for Caution

Despite the optimism, there are still areas where the Bears could experience regression.

Two key statistics from last season stand out.

Chicago recorded seven comeback victories, the most in the NFL.

While thrilling for fans, comeback wins often involve an element of luck and rarely repeat at the same rate from year to year.

The Bears also led the league in defensive takeaways, another category that can fluctuate dramatically from season to season.

Maintaining that level of turnover production is extremely difficult.

Health Was Also a Major Factor

One of the most overlooked aspects of Chicago’s 2025 success was the team’s remarkable health.

The Bears’ starting offensive line played more than 90% of the team’s snaps, an unusually high level of durability in a league known for injuries.

Replicating that level of health is far from guaranteed.

Complicating matters further, Pro Bowl center Drew Dalman unexpectedly retired at just 27 years old, forcing Chicago to adjust its offensive line plans.

The Core Is Still Rising

Even with those concerns, the foundation of the Bears’ offense continues to improve.

Williams is surrounded by an exciting group of young playmakers, including:

• Rome Odunze
• Luther Burden III
• Colston Loveland

Together, they form a receiving core that many believe could become one of the most dynamic groups in the NFL.

If Williams continues to develop and the offense maintains its efficiency, Chicago could quickly become one of the most dangerous teams in the NFC.

And if that happens, surpassing nine wins might not just be possible—it could become the expectation.