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5 games ESPN says the Chicago Bears are least likely to win on 2025 NFL schedule

Originally posted on Chicago Bears on SI | By Bryan Perez | Last updated May 17, 2025 12:20 PM ET

The Chicago Bears are a popular pick to be this year's turnaround team in the NFL. Armed with Ben Johnson as head coach and second-year quarterback Caleb Williams, who will finally play behind an NFL-worthy offensive line, the outlook in Chicago is bright.

But it's one thing to predict and project success; it's another to actually achieve it.

This is familiar territory for the Bears. Optimism is always high after signing a few big-name free agents and selecting a top-10 pick in the NFL Draft, which has become an annual tradition for this franchise.

What's different this year, however, is the organizational structure that's in place. Starting with Johnson, the Bears finally feel like a team with an adult in charge. And not just any adult; he's the most highly sought-after head coach in a decade.

Johnson's first season in Chicago won't be easy. The Bears' 2025 schedule is one of the toughest in the NFL, and there are five games in particular that stand out as tougher than most.

ESPN recently published its 2025 NFL projections, which included a projected win total. In a weird twist, the Bears landed at 8.5 wins -- essentially, flip a coin on whether Chicago will have a winning or losing record this season.

Included in ESPN's projected win total is a breakdown of every game and the Bears' win probability for each opponent. Five games stood out as particularly challenging, with Chicago having a 41% chance of winning or worse.

Chicago Bears' five toughest games in 2025

Week 2 at Detroit: 24% chance of winning

Week 8 at Baltimore: 27% chance of winning

Week 13 at Philadelphia: 35% chance of winning

Week 14 at Green Bay: 41% chance of winning

Week 18 vs. Detroit: 31% chance of winning

The season (basically) kicks off with the Bears' toughest projected matchup in Week 2 at the Lions. The 24% chance of winning is the lowest Chicago has all season, and it's easy to understand why. Detroit is one of the Super Bowl favorites in the NFC, and with the Bears in Year 1 of a new era, it's fair to assume there will be an early-season adjustment period.

Indeed, the same can be said for teams facing the Chicago Bears, especially early in the year. There won't be any film on this Bears team, giving Johnson and Williams a bit of an advantage against teams like the Vikings (Week 1), Lions (Week 2), and Cowboys (Week 3).

The same can't be said for Week 8's game against the Ravens. It's the second-lowest win probability for the Bears, and, at first glance, does appear to be one of the toughest matchups in 2025.

I'm a bit surprised that Chicago has a 35% chance of defeating the Eagles on Black Friday; that seems high to me. In fact, I would've expected the Bears would have a worse chance of beating the Eagles and Ravens than the Lions, which will make an early-season upset win that much sweeter for Ben Johnson.

This article first appeared on Chicago Bears on SI and was syndicated with permission.

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