Caleb Williams Picks, Predictions & Best Bets for Cowboys vs Bears

The Dallas Cowboys passing defense has underwhelmed thus far, and our expert NFL prediction expect Bears QB Caleb Williams to fire at least a pair of scoring strikes.

Zak Hanshew - Betting Analyst at Covers.com
Zak Hanshew • Betting Analyst
Sep 20, 2025 • 10:26 ET • 4 min read
Caleb Williams of the Chicago Bears
Photo By - Imagn Images. Caleb Williams of the Chicago Bears.

The Chicago Bears lost a close one to the Minnesota Vikings in Week 1 before getting demolished by the Detroit Lions in Week 2. They’ll look to get back on track against the Dallas Cowboys this week and avoid falling into a 0-3 hole.

Let’s dive into our best NFL player props for Cowboys vs. Bears on Sunday, September 21, while highlighting Caleb Williams odds, who gets a juicy matchup with Dallas’ bottom-of-the-barrel defense.

Read on for my NFL picks for Sunday, September 21. 

Caleb Williams prop pick

Caleb Williams best bet: Over 1.5 passing touchdowns (-122 at FanDuel)

Caleb Williams certainly didn’t have a nose for the endzone as a rookie, firing off just 20 passing touchdowns across 17 games. He’s on track to be a bit better in Year 2, as he’s delivered three passing touchdowns through the first two weeks of the 2025 season.

All of Williams’ scores have gone to fellow sophomore Rome Odunze, who broke out in Week 2. The chemistry between the pair should continue to blossom as the season progresses. It wouldn’t be surprising if Odunze found the endzone for a third straight game on Sunday, but Williams has other reliable options at his disposal.

Williams can get DJ Moore and Cole Kmet involved, and he has yet to unlock rookie No. 10 pick Colston Loveland. I expect Williams to share the love in this one and find multiple receivers for touchdowns. D’Andre Swift is a great receiver out of the backfield, but he’s questionable with a quad injury. If he’s sidelined, Ben Johnson may have to lean heavily on Williams and the passing game.

Through two games, Dallas’ defense has allowed 61 points, good for the fifth-most in the NFL. They’ve allowed the third-most passing yards (283), fourth-most passing yards per attempt (8.8), second-highest completion percentage (76.6), and third-most total yards (404).

The Cowboys got smoked by Russell Wilson to the tune of 450 passing yards and three passing touchdowns last week. Expect Williams to come out firing and toss a pair of tuddys against a terrible Cowboys secondary.

Caleb Williams same-game parlay

Caleb Williams Over 1.5 touchdown passes

Rome Odunze Over 61.5 receiving yards

CeeDee Lamb anytime touchdown scorer

Odunze broke out with a monster effort in Week 2, albeit in a blowout loss to the Lions. In that one, the second-year man corralled seven catches for 128 yards and two scores.

The Washington product averaged just 5.9 targets per game as a rookie, but Williams is looking to him early and often, and Odunze has 20 targets through the first two games of the 2025 campaign. 

Facing Dallas’ vaunted secondary, I expect him to have another big day.

Lamb is off to a hot start, totaling 16 catches and 222 yards on 24 targets through the first two weeks of the season. Despite the monster receiving yardage, he’s failed to find the endzone.

That will change in Week 3. Chicago gave up two passing touchdowns in Week 1 before getting torched for five more in Week 2. 

The seven passing touchdowns are the most allowed in the NFL this season, and CeeDee Lamb should find paydirt as Dak Prescott continues to look in his direction.

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Zak Hanshew - Covers
Betting Analyst

Zak Hanshew has been covering fantasy sports and sports betting since 2018. In addition to Covers, he has also written for Rotoworld and has spent time at FantasyPros, RotoWire, OwnersBox and Sportsbook Review. In his spare time, he can be found spending time with his wife and four kids, playing his guitar, watching Simpsons re-runs, or getting some shots up on the court.

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