Dallas can expect a warmer reception this time in Chicago

by Aug 14, 2025

The last three times the Dallas Cowboys played the Bears in Chicago, both games were played in December. Two were on a Thursday night, the other was a Monday night game.

If you’ve ever been to Chicago in December, there is one constant.

It’s always cold, especially after the sun goes down.

This year at least, the Cowboys will be hitting Chicago in September. And the sun should still be out by the time this game ends, even if overtime is in play.

That doesn’t mean it won’t be a hard game to win.

  • Who: Chicago Bears
  • Where: at Soldier Field in Chicago, IL
  • When: Sept. 21st, 3:25 p.m. (CDT)
  • How (to watch): FOX

The last time the two teams met, back in 2022, the Cowboys were facing a second-year quarterback in Justin Fields. They very nearly let him pull out the win.

Right and Wrong: Cowboys vs Bears

This year they are facing a second-year quarterback in Caleb Williams.

The Cowboys have a history of letting young phenom quarterbacks have career games against them.

For Dallas, it will be a homecoming of sorts for two members of the team. Defensive coordinator Matt Eberflus was the Bears’ Head Coach until the 13th week of the 2024 season.

Linebacker Jack Sanborn was on the Bears’ roster for his first three years before joining the Cowboys during this offseason.

All-Time Marks

Dallas is 35-25 all-time in the third week of play. They’ve had two games lost to strikes/lockouts (1982, 1987).

Three bye weeks — 1999, 2003, and 2006 – fell on Week 3 of the schedule.

The Cowboys are 18-14 on the road during this week, but have beaten Chicago all three times that the teams have met in the third game of the year.

Dallas won at home in 1979, won in Chicago in 2007, and completed the trifecta with a home win in 2016.

Overall, the Cowboys are 16-12 against the Bears with the two teams evenly splitting the 14 games played at Chicago. While Dallas won the last meeting in 2022 at home, 49-29, the Bears defeated the Cowboys 31-24 in Chicago on a Thursday night in December 2019.

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The Cowboys’ last win in Chicago came on a Thursday night in December 2014 when Tony Romo out-dueled Jay Cutler, 41-28.

The Prediction

As with the Giants game the week before, this really is a must-win game for Dallas. Many of their early-season games will be must-win games.

That six-game stretch against teams that made the playoffs in 2024 toward the end of the year will loom large over the entire 2025 season.

Dallas 28, Chicago 17 (Predicted season record so far: 2-1).

Richard Paolinelli

Richard Paolinelli

Richard Paolinelli is a sports journalist and author. In addition to his work at InsideTheStar.com, he has a Substack -- Dispatches From A SciFi Scribe – where he discusses numerous topics, including sports in general. He started his newspaper career in 1991 with the Gallup (NM) Independent before going to the Modesto (CA) Bee, Gustine (CA) Press-Standard, and Turlock (CA) Journal -- where he won the 2001 Best Sports Story, in the annual California Newspaper Publishers Association’s Better Newspapers Contest. He then moved to the Merced (CA) Sun-Star, Tracy (CA) Press, Patch and finished his career in 2011 with the San Francisco (CA) Examiner. He has written two Non-Fiction sports books, 11 novels, and has over 30 published short stories.

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