Oops!… I Did It Again: Chicago Bears Game-By-Game Schedule Prediction

bears qb Caleb Williams and head coach matt Eberflus
bears qb Caleb Williams and head coach matt Eberflus

We’re in a bit of a holding pattern as the preseason ended a week ago, yet we still have over a week until the Bears kick off their season against the Titans.

With us having some t𓃲ime to kill before the Bears begin their Super Bowl c෴ampaign, I figured it was a good time to go through the schedule and make some game-by-game predictions.

Last year, Luis, Patrick, and I did this on our Bears show and I’ll admit it, I got a little ahead of myself. I was all in on the Justin Fields experience (or at least I was convincing myself that I was) and I got somewhat, kind of over-excited and overambitious. I had Chicago going 12-5. Hand up, that was on me. I owned it throughout the year on the postgame shows. At least the 0-4 start didn’t give me the chance for any false hope!

While last year there was clearly false hope, this year there’s a whole lot of evidence to support having real hope. Maybe not for a Super Bowl, but for a team that can compete in the toughest division in the NFC, make a push for the playoffs, is set up very well for the long term, and has their quarterback for the next decade plus.

I’m fired up, I’m ready for the Titans. Let’s predict some games.

bears qb Caleb Williams
© Daniel Bartel-USA TODAY Sports

Week 1 – Titans at Bears: Win

No way they start out with a loss at home against a team that’s presumably taking a step back this year, right?!? I’m both nervous because I’ve been hurt in the past, but optimistic that this team just feels different. Caleb Williams gets his first win out of the way early.

Record: 1-0.

Week 2 – Bears at Texans: Loss

I did so many mental gymnastics in my brain trying to make this one a win. And it still could be. But it’s Houston’s home opener. They’ll probably be 1-0. Expectations in Houston are sky-high too. I think the Bears are farther along than where Houston was when C.J. Stroud debuted last year (not that big of a reach, I know) but this just feels like a very tough spot and a difficult first road start for Caleb.

Record: 1-1.

Week 3 – Bears at Colts: Win

I know it’s on the road, but this one has got to be a win, especially if Week 2 is a loss. Anthony Richardson is talented, but still very raw. The early portion of the schedule gives Chicago an opportunity to get out to a fast start, they have to take advantage here.

Record: 2-1.

Week 4 – Rams at Bears: Win

If this game was in LA, I’d mark it as a loss. Even at home, this one will be pretty tough I’d imagine. But the Rams have a tough start to their schedule, and they got off to a slow start last year before making a playoff run late. Why can’t Chicago take this one at home?

Just for fun, here are the in one of my favorite games I’ve ever watched. (Luis: It was rare, I was there, and I remember it all too well.)

Record: 3-1.

Week 5 – Bears vs Panthers: Win

It better be.

Record: 4-1.

demarcus walker bears training camp
Mandatory Credit: Daniel Bartel-USA TODAY Sports

Week 6 – Bears vs Jaguars (in London): Loss

After a 4-1 start riding a lot of momentum, the Bears get tripped up across the pond against a solid, well-coached team that’s more than used to playing over there and all the changes to routine that come with it.

Record: 4-2.

Week 7 – BYE

Record: 4-2.

Week 8 – Bears at Commanders: Win

This matchup will most certainly garner a lot of national hype with the top two picks in the draft facing off. It’s also going to be a homecoming for Caleb. Though there might be some potential distractions, they’re just the better team in this one and they should have the better QB too.

Record: 5-2.

Caleb Williams Bears
© Kirby Lee-USA TODAY Sports

Week 9 – Bears at Cardinals: Win

Arizona had a nice offseason, and they’ve certainly improved from last year. That said, their defense still has so many holes and their offense is still relying on Kyler Murray to be healthy. The Bears secondary will do their best to take away Marvin Harrison Jr, and they should come away with a road win here.

Record: 6-2.

Week 10 – Bears vs Patriots: Win

Similar to the Carolina game, it better be. Who knows if it’s Drake Maye by now or still Jacoby Brissett, but it really shouldn’t matter. After this one, the schedule really starts to pick up so this one has got to be a W.

Record: 7-2.

Week 11 – Bears vs Packers: Win

Homer pick? Maybe, maybe not. I refuse to believe Chicago will come outﷺ flat again against Green Bay like they did multiple times last season. And no matter what the record is, I think this is a HUGE game for Matt Eberflus and getting over that hump.

Record: 8-2.

Week 12 – Bears vs Vikings: Win

Ok, I’m getting a little nervous about the win total piling up, but whether it’s Sam Darnold, Nick Mullens, or even our old friend Brett Rypien this should be a win. Minnesota isn’t a bad team, but they seem to be a step behind the rest of the NFC North this season. At home with the better QB, this should be a W.

Record: 9-2.

Week 13 – Bears at Lions: Loss

Detroit is still a very good football team, and this will be Chicago’s first road game against a likely playoff team since Week 2. Tough environment, tough crowd, tough opponent, no shame in dropping this one.

Record: 9-3.

Week 14 – Bears at 49ers: Loss

If they win this one I’ll be ecstatic. But yeah, I’m not going to go into this one with the highest of expectations.

Record: 9-4.

Week 15 – Bears at Vikings (MNF): Win

Even though the previous two games were against likely playoff opponents on the road, I’m still coming into this one nervous if it’s on a two-game losing streak, and the first one of the season. Minnesota gets loud, they will be in those all-white uniforms too. However, the Bears are just better on both sides of the ball. And at this point in the season, who knows where the Vikings’ record will be at this stage of the season?

Record: 10-4.

Week 16 – Bears vs Lions: Win

If this were Week 5 or 6, I migꦿht be reconsidering here. But Jared Goff HATES playing in the cold (did I mention the SNF win over the Rams in 2018??). Bears get the win and even the series with the Lions.

Record: 11-4.

Mandatory Credit: Jamie Sabau-USA TODAY Sports

Week 17 – Bears vs Seahawks (TNF): Loss

Thursday night games are weird. The Bears will be in the murderers’ row portion of their schedule having just played five division games plus the Niners in their last six weeks. Seattle pulls off the upset here because weird things happen on Thursday nights and the Bears will also probably be wearing those dumb orange uniforms.

Record: 11-5.

Week 18 – Bears at Packers: Win

I refuse to pick the Bears to lose to Green Bay this season. Tough spot, sure. We don’t know who will be playing for what. But Caleb is the QB that flips the script on this rivalry.

Record: 12-5.

New season, same record! Bears finish the season 12-5. Seeꦅ you all in the play💫offs.

Chicago Bears cornerback Tyrique Stevenson (29) breaks up a potential touchdown reception against Green Bay Packers wide receiver Romeo Doubs (87) in the first half during their football game Sunday, January 7, 2024, in Green Bay, Wisconsin.
© Dan Powers/USA TODAY NETWORK-Wisconsin / USA TODAY NETWORK

written by

Matt is from the Chicagoland area and has been working in Chicago sports since 2015 with stops at WGN Radio, the Chicago Blackhawks, Stadium, and NBC Sports Chicago prior to landing at Betsperts. Matt covers just about everything for Betsperts and Bleacher Nation but focuses on the NHL and college football🍸.

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