Football fans often overlook the Chicago Bears vs Buffalo Bills matchup because they only see each other every four years in the regular season. But honestly, if you've been paying attention to the joint practices and the preseason fireworks lately, you'll know there's a lot more under the hood than just two teams from different conferences.
The last time these two met when it actually "counted" was Christmas Eve in 2022. It was freezing. Soldier Field was basically an ice rink. The Bills ended up winning that one 35-13, but the score didn't tell the whole story of how gritty that game felt. Since then, both franchises have undergone massive identity shifts. The Bills moved on from the Stefon Diggs era, and the Bears finally—after what feels like a century of searching—landed Caleb Williams.
What Really Happened with Chicago Bears vs Buffalo Bills in 2024
Most people only care about the regular season, but the August 2024 preseason opener in Orchard Park was actually a massive turning point for Chicago. The final score was 33-6 in favor of the Bears, but nobody was talking about the win. They were talking about the debut.
Caleb Williams stepped onto the field at Highmark Stadium and looked... comfortable. That's the word everyone used. He only played two series, but he went 4-of-7 for 95 yards. The highlight? A shovel pass to D’Andre Swift that went for 42 yards. It was the kind of play that makes a fanbase believe the curse is finally over. On the other side, the Bills were keeping Josh Allen under wraps, which is standard, but the gap in depth was startling.
The Mitchell Trubisky Revenge (Or Lack Thereof)
There's a weird piece of trivia here: Mitchell Trubisky. The former Bears' first-round pick was back in Buffalo for that 2024 game. Seeing him in a Bills jersey while the Bears' new savior took the field felt like a glitch in the Matrix for Chicago fans. Trubisky struggled, going 10-of-18 for 82 yards.
It’s a reminder of how quickly the NFL moves. One year you're the face of a franchise in the Windy City, the next you're the "break glass in case of emergency" guy behind Josh Allen.
The Statistical Reality of the Series
Historically, the Bears actually hold the upper hand. In their all-time regular-season meetings, Chicago leads the series 8-6. It’s a slim margin, but it exists.
- Biggest Bears Win: 40-7 in 2006. That was the Super Bowl run year.
- Biggest Bills Win: 35-13 in 2022.
- Average Margin of Victory: Roughly 10 points.
When these two play, it’s rarely a nail-biter. One team usually finds a way to physically dominate the other. In 2022, it was the Bills' rushing attack that gushed the Bears for 254 yards. In 2024's preseason, it was the Bears' defense, led by a Micah Baskerville pick-six, that turned the game into a blowout.
Why the 2025 Matchup Flipped the Script
Fast forward a bit. By the time we hit the 2025 preseason, the narrative shifted again. Caleb Williams wasn't a rookie anymore; he was a division winner. When the Bears and Bills met again in the '25 preseason, Williams threw a 36-yard laser to Olamide Zaccheaus on his very first drive.
It showed a level of "clean operation" that Matt Eberflus had been dreaming about. No pre-snap penalties. No sacks. Just rhythm. The Bills, meanwhile, have been trying to figure out how to keep Josh Allen healthy while their defense goes through a youth movement.
Why This Matchup Still Matters
You might think an AFC vs NFC game is just a scheduling quirk. It’s not. These teams are mirror images in terms of market passion. Buffalo fans (the Bills Mafia) and Chicago fans are both weather-hardened, loyal to a fault, and desperate for a ring.
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The 2024-2025 window has shown that the "gap" between a rebuilding Bears team and a perennial contender like the Bills is closing. While Josh Allen remains the gold standard for dual-threat quarterbacks, Caleb Williams' rookie records—4,030 total yards and a 354-pass streak without an interception—suggest he's chasing that same tier of elite play.
Actionable Insights for Fans and Bettors
If you're looking at the next time these two square off, keep these factors in mind:
- Watch the Trenches: The Bills' offensive line has been surprisingly susceptible to speed rushers lately. If the Bears' defensive front remains aggressive, they can neutralize the Bills' deep threats.
- Weather is a Variable, Not a Constant: Both teams play in "bad weather" cities, but the Bills usually handle high winds better due to Allen’s arm strength.
- The "Revenge" Factor: Any time a former player or coach (like the Ryan Bates trade in 2024) is involved, the intensity ticks up.
Keep an eye on the injury reports regarding the secondary. In their most recent encounters, the Bills have struggled when their starting safeties are out, specifically against tight ends like Cole Kmet, who has become a safety valve for the Bears' offense.
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The next time Chicago and Buffalo meet in the regular season, it won't just be a cross-conference game. It'll be a measuring stick for whether the Bears have truly joined the NFL's elite or if Buffalo still owns the cold-weather crown. Check the defensive rotation for the Bears' interior line before placing any player prop bets on James Cook, as he's historically the "X-factor" that breaks this specific matchup open.