May. When you’re a football fan, the fifth month of the calendar always feels a bit sad. The NFL Draft is long gone, and your team’s rookies are already secured in their new homes. We still haven’t “REALLY” started summer yet, so the start of Training Camp is STILL a healthy distance away from us.

We just……don’t have a lot of football related content to wet our beaks with at this point in the year. That is why when the NFL released the league’s schedule for the upcoming season yesterday……fans couldn’t HELP but get excited! We couldn’t HELP but glom on to every piece of content we could find, in order to scratch that “football itch” that has plagued us since February.

For immediate release: pic.twitter.com/cXC10lLZs2

— Chicago Bears (@ChicagoBears) May 15, 2025

The question that arises from this though is…..what are the biggest “highlights” from Chicago’s upcoming schedule? What are some of the biggest games on this list that we should be looking out for, and what are some match-ups that could give Ben Johnson and co. trouble? Well……

1. Chicago Bears vs. Washington Commanders – 10/13

The problems that this team faced last season…..they all stemmed from this one particular game. Caleb Williams and co. were flying high through the first few weeks of the season. They were performing just like we thought they would with a brand new quarterback, and an offense littered with weapons.

But then……this happened, and everything changed.

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JAYDEN DANIELS HAIL MARY! @COMMANDERS WIN! pic.twitter.com/BsQ0Z84Rko

— NFL (@NFL) October 27, 2024

It was a moment that Bears fans wanted to forget, and tried to forget, throughout the remainder of the year. But it just kept living rent free in our minds like a crappy commercial jingle, or a moronic mnemonic device from high school.

But now, the Bears have a chance to right the wrongs of yesteryear. They will be returning to that same place, in that same town, to hopefully fix their mistakes. It will be an emotional night, that’s for sure. But with the additions that this team has made over the offseason….you shouldn’t expect anything less than a barn-burner.

2. Chicago Bears vs. Baltimore Ravens – 10/26

The Baltimore Ravens are a very run-heavy team, we all know this. With names like Lamar Jackson and Derrick Henry in the backfield, this team has proven to be DEADLY at every turn on the offensive side of the ball. Why could that be a problem, you may ask? Well…..it’s because the Chicago Bears were a collection of turnstiles in cleats last season when it came to defending the run.

I’m not kidding when I say this. During the 2024 season, the Chicago Bears defense allowed an average of 136.3 rush yards per game, which is a MAJOR step down when compared to the 86.4 YPG they surrendered in 2023. They COULD NOT defend opposing runners to save their lives, and now they have to go up against the most dynamic backfield in football today?

That, my friends, is going to be such a BIG TIME SWEATFEST. Sure, Chicago has Dennis Allen at the helm. Sure, they brought in guys like Grady Jarrett to help solidify the middle. But if they don’t fix this issue, and have a plan for what’s ahead…….one could say that Derrick Henry’s going to have a DAY come Week 8.

3. Chicago Bears vs. Philadelphia Eagles – 11/28

If you are looking for a “hostile environment” for your favorite team to play in, then look no further than Lincoln Financial Field the year after the Philadelphia Eagles win a Super Bowl. Sure, Philly fans are as raunchy as they come. They are a group of loud, and brash individuals, who don’t care who they offend. But when you add a championship to the mix……they can become some of the most INSUFFERABLE human beings imaginable.

Not only that…..the team is pretty good on their own too. The Eagles had a Top-5 scoring offense in the league last season (29.0 PPG), that was lead by the likes of Jalen Hurts and Saquon Barkley. Not only that; they also had the most stout defense in the league as well, giving up a measly 18 points per contest throughout the regular season.

Simply put; Caleb Williams and co. are going to have their hands full when they fly out to PA in November. Sure, the defense could probably hold their own and keep them in this game. But if the offense can’t respond and do their job…..this may be a rough one for the navy and orange.

4. Cleveland Browns vs. Chicago Bears – 12/14

I’m just going to come out and say it; I have no reason to believe that this will be a “fun game.”  This is not a “key match-up,” or a “highlight” on the schedule. The Cleveland Browns are having a hard time finding their identity, and they have been an utter disaster ever since Baker Mayfield departed a number of years ago. They are who they are, and that’s the end of it. They will most likely lose this game.

HOWEVER…..I will say that this “quarterback conundrum” that the Browns currently have is very interesting to me. As of writing this, HC Kevin Stefanski currently has five QBs rostered, including the likes of;

– Deshaun Watson
– Joe Flacco
– Kenny Pickett
– Shedeur Sanders
– Dillon Gabriel

It’s weird, I know. The thought of me being interested in which quarterback will start for this crappy team against my Bears is the most minuscule problem in the world. But for some reason…..it intrigues me. Will it be Shedeur? Gabriel? Or will old-man Flacco park his rascal scooter on the sideline, and give this game another go? Who knows! I just can’t wait to see who it is come Week 15.

In the end though, as always…..what do I know? I’m just a guy from the Midwest, with a beer and a laptop, trying to make sense of this world.