Dallas Cowboys vs Chicago Bears Prediction, Odds and Picks for Today, 09/21/25

Both the Dallas Cowboys and Chicago Bears could desperately use a win here, although the Bears even more so. The Ben Johnson era in Chicago has started off in disastrous fashion, as the team is now 0-2 after getting clowned by the Lions last week 52-21. He needs to save face with a win here, but nothing I’ve seen from Caleb Williams (or the defense) give me the impression that’s likely. The Cowboys picked up a thrilling win last week despite Russell Wilson having one of the best games of his career, and Dallas’ only loss this year was a close one to the defending champion Eagles.

Dak Prescott is lightyears ahead of Williams, who appears to have made very little progress from a shaky rookie season. He continues to run around with the ball way too much like he’s still in college, and he took another 4 sacks last week against Detroit. The defense is an even bigger concern now after getting torched by a Lions team that looked helpless themselves in Week 1, and after allowing JJ McCarthy to mount a heroic 4th quarter comeback against them in their opener.

Expectations were low for the Cowboys this season after Micah Parsons was traded away, but this is still a very good team with a lot of talent. The offseason addition of George Pickens has helped open things up for CeeDee Lamb, and I think Jake Ferguson is quietly one of the best tight ends in the league. Dallas outgained Philadelphia in Week 1, and very nearly won on the road as massive underdogs. I think they’ll take care of business here at Soldier Field.

Cowboys vs Bears prediction: Cowboys -1 available at time of publishing. Playable to -1.5

If you’re looking for a new sportsbook for the football season, we recommend checking out Fanatics Sportsbook. New users can get up to $100 back in FanCash EVERY GAMEDAY UNTIL OCTOBER if their football bet loses! Join Fanatics Sportsbook, where you can bet on our Cowboys vs Bears predictions.

This one definitely has all the makings of a shootout. Chicago’s defense is a liability, and Jared Goff just made them look silly last week even though theoretically Ben Johnson should’ve known about all of his and the Lions’ weaknesses. Goff had 334 yards and five touchdowns as Detroit dropped 52 on them, and there were red flags for the Bears the week before even against a mostly hapless JJ McCarthy. If that game against the Vikings can end with 51 total points, I certainly think this one should.

The Cowboys have one of the best offenses in the league, with a top tier quarterback, a great 1-2 punch at receiver, and an emerging tight end. Dallas’ defense on the other hand is a different story, and they made Russell Wilson look like prime Seahawks Russ last week as they gave up 34 points to the Giants. If the Giants can score 34 on them, I think even the Bears will be able to do enough here to help send this game over 50.

Over 50 available at time of publishing. Playable to 50.5