Four Chicago Bears Are Earning Contract Extensions For 2027 and Beyond

With Caleb Williams still on a cheap rookie deal for the next few years before his inevitable monster contract extension kicks in down the road, the Chicago Bears will have some financial flexibility.

And, with that flexibility, the Bears can dump resources into some players at other positions who have proven their worth during their time in Chicago.

At the halfway point of the season, there are four Bears players who are either in a contract year or will be in 2027 that have earned an extension from the team with their play.

Theo Benedet

After falling short in the starting left tackle competition at camp, Benedet was thrust into the role after Braxton Jones went down with an injury that proved to be a season-ending issue.

The Bears probably could've turned to Ozzy Trapilo at some point in the last few weeks, but with Benedet playing well, they haven't done that.

Through nine games, Benedet sports a respectable 68.4 pass-blocking grade, according to Pro Football Focus, and he has allowed just one sack and 18 pressures.

In the run game, Benedet is sporting a grade of 73.3, which ranks 19th among tackles in the NFL.

Benedet is an exclusive rights free agent after this season, so the Bears have some control. However, they might want to lock him up for more than just next year as a potential long-term left tackle or, at the very least, a long-term swing tackle.

Jonah Jackson

When the Bears acquired Jackson in a trade with the Rams in 2025, his career was in trouble. Jackson missed most of the season with an injury and wasn't effective when on the field.

But Jackson has flipped the script with the Bears and once again looks like one of the best guards in the NFL. This season has been particularly impressive, with Jones ranking fourth in run-blocking grade (85.1) and fifth in overall grade (83.1) among guards while not permitting a sack and giving up just 16 pressures.

Jackson is under contract for another year, but he doesn't have any guaranteed money left on his deal, which makes him an obvious candidate for a long-term extension even more.

Chicago would benefit from locking him up long term, also, as the team can lower his $12.2 million cap hit for 2027 in the process.

D'Marco Jackson

Jackson started his ascension last season, when he was a pleasant surprise for the Bears in his first year in Chicago.

And the veteran linebacker has picked up where he left off and is seeing an increased role as a result, with his snap share going from 26% last season to 43% this season.

Jackson remains one of the best coverage linebackers in the NFL, as evidenced by his PFF grade of 76.2 in that area, which ranks sixth at the position. He also has one interception.

His run defense hasn't been great, but Jackson's coverage ability makes him a great complement to Devin Bush.

Jackson still has one more year left on his deal, but with T.J. Edwards getting long in the tooth, the Bears might want to lock Jackson up for the long haul before his value rises even more.

Cam Lewis

Lewis has no doubt proven his worth this season thanks to his versatility and amounts to a home-run signing for the Bears.

With injuries at slot cornerback and safety, Lewis has split his time between the two positions and has played well, with his 70.2 coverage grade ranking 17th among safeties.

Lewis isn't going to be a free agent in 2027, but the Bears might be wise to lock him up for another year or two before 2028, and he certainly deserves a raise, also.

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