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Daunting Stretch of Games Will Define Chicago Bears’ Season

May 27, 2025 by Last Word On Pro Football

The national media and Bears fans around the world have playoff aspirations for this team. All of their flashy coaching changes and offensive line improvements have not gone unnoticed. However, a portion of their schedule proves to be more daunting than the rest. According to FOX’s Greg Auman, this 4-game stretch in the Bears’ schedule is one of the 10 toughest stretches in the entire league.

Daunting Stretch of Games Will Define Chicago Bears’ Season

Weeks 11 to 14

Caleb Williams
Dec 16, 2024; Minneapolis, Minnesota, USA; Chicago Bears quarterback Caleb Williams (18) throws a pass against the Minnesota Vikings during the third quarter at U.S. Bank Stadium. Mandatory Credit: Jeffrey Becker-Imagn Images

The Bears’ tough stretch of the schedule falls in weeks 11 through 14. Over the course of those four weeks, they will have to play in Minnesota, at home against the Steelers, and then on the road in back-to-back primetime contests against the Eagles and Packers.

Coming into this stretch, the Bears could be around or even above .500. These games will either prove they aren’t ready yet or send a message to the league that Chicago is a contender.

At Minnesota

This won’t be the first matchup against the division rival Vikings in 2025, as these teams will kick off the 2025 season on Monday Night Football at Soldier Field in week one. J.J. McCarthy will have some reps under his belt and will have already seen what this Dennis Allen defense can throw at him. The Vikings didn’t make too many non-quarterback changes from last season, as their skill positions remain mostly the same, headlined by Justin Jefferson, T.J. Hockenson, and Aaron Jones.

On the other hand, Caleb Williams and Ben Johnson will have had nine games up until this point to iron out any early-season kinks and develop strong, week-to-week game plans that properly utilize the offensive arsenal at their disposal. As the Bears improved their interior offensive line, the Vikings added to their interior defensive line by signing Javon Hargrave and Jonathon Allen in free agency.

The trenches will be the key to winning this game, as the team that wins at the line of scrimmage will likely come out on top.

Vs Pittsburgh

The Steelers’ offense has been lackluster to say the least ever since the “Killer B’s” era ended in Pittsburgh a while back. They’ve gone through many different faces at the quarterback position since Ben Roethlisberger retired in 2021.

However, there have been rumors swirling all offseason about a familiar face coming to play for the Steelers. Aaron Rodgers hasn’t made a decision yet, but odds are that he will choose Pittsburgh as one of his final destinations in his dominant career.

The narratives surrounding this game and the man who “owns the Bears” will be loud, so the Bears will need to keep themselves in check for the matchup.

Even without looking at what the Steelers’ offense might be in 2025, head coach Mike Tomlin has fielded a fantastic defense the last few years. Superstar pass rusher T.J. Watt and ballhawk safety Minkah Fitzpatrick will surely be a tough test for Williams.

At Philadelphia

How can the game against the reigning Super Bowl champions not be considered a tough game? The Eagles have firepower on both sides of the ball and only seem to be getting better each year. There aren’t any glaring weaknesses on the Eagles’ roster, so the Bears will just have to find a way to win.

Jalen Hurts was clutch in the playoffs last year, and he will be throwing to star receivers A.J. Brown and Devonta Smith. Their defensive line has talent deep into their reserves, and they have an extremely young yet productive cornerback room.

Oh, did anybody forget about Saquon Barkley‘s NFL Offensive Player of the Year Award from last year? Didn’t think so. This game will be tough in all three phases of the game. If the Bears win, it will tell the entire league that the Bears can compete with the best.

At Green Bay

For all Bears players and fans, this game has been on their minds before the schedule was even announced. Everyone and their mother look forward to Bears/Packers week regardless of their loyalty. Nobody in Chicago cares about the Bears’ 3-17 record against Green Bay in the last 20 contests, or the fact that there was a 10-game losing streak since claiming the division crown in 2018. The only game that matters to them is the most recent one played on January 5, 2025, when the Bears walked off of Lambeau Field with a victory after Williams led a game-winning drive ending in a Cairo Santos field goal to win 24-22.

Unfortunately for the Bears, the Packers are only thinking about that game, too, and will be seething with revenge. This game will have everything you want in a rivalry. Williams vs Jordan Love, Johnson vs Matt Lafleur, and Bear vs Cheese. Maybe not that last one, but you get the point.

Even though this is the final game of this grueling stretch, it will be far from the easiest. If the Bears want to become the contender they believe they are, these four games will define their season. If they come out of this stretch alive, they could make some noise come playoff time.

Main Image: David Banks – USA Today Sports

The post Daunting Stretch of Games Will Define Chicago Bears’ Season appeared first on Last Word on Pro Football.

Filed Under: Bears

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