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Windy City Gridiron

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Chicago Bears 2026 Offseason Superlatives: Most Worried About

This WCG roundtable series was inspired by this Tweet from our guy Jacob, who gave six 2026 Chicago Bears superlatives for the offseason. We’re going to take them one by one, and we’ll give a couple two tree sentences for each. We wrap up the series with what we’re most worried about this season. Jacob […]

NFL

The Bear’s Den, June 2, 2026

THE DAILY SPONGIE SPECIAL BEARSSSSSS What’s next for the Bears after their stadium bill stalls in Springfield I dunno. Do you know? Gov. JB Pritzker ready to own possible Bears departure after Illinois House punts on stadium bill Please keep any non-stadium political discussion out of my Den. Bears blocked in Illinois: House spikes late-session […]

30 Day Challenge: Earliest Chicago Bears Memory

As the month of June begins, the Windy City Gridiron staff is embarking on something we are calling the “30 Day Challenge” related to the Chicago Bears. Each day of the month, there will be a new feature article published by one of our staff members on a unique topic. We’ll give our own answer […]

NFL

Chicago Bears 2026 Offseason Superlatives: Breakout Candidate

This WCG roundtable series was inspired by this Tweet from our guy Jacob, who gave six 2026 Chicago Bears superlatives for the offseason. We’re going to take them one by one, and we’ll give a couple two tree sentences for each. This time, we gave our pick for the Bears player we predict to break […]

NFL

2026 NFC North top 50 players: No. 21-30

The 2026 NFL season is a few months away, and the anticipation for week one is at an extremely high level. As the NFL Network has done their player consensus Top 100 ranking each year, Windy City Gridiron’s staff has put together a roundtable over the last few seasons of the best players in the […]

Chicago Bears Post June 1st Trade Market Roundtable – Part 2

Earlier today we dropped the first part of this roundtable discussion between myself and a few others here at Windy City Gridiron. Now we get into whether or not we feel that the Chicago Bears will indeed make a move, and what some of the likeliest deals are to be made elsewhere. A trade market […]

NFL

Chicago Bears Stadium Bill fails to pass Illinois Legislature

The Illinois legislature worked late into the night on Sunday and into the early morning hours of Monday on bills that would be passed this session. Among those was consideration of the Amendment to House Bill 958 (the Chicago Bears Stadium Authority Bill) that would establish the tax and stadium financing structure the Bears had […]

NFL

Ten Chicago Bears with the most to prove in 2026: 10. Tory Taylor

It’s officially June, which means it’s time to start our annual list: Ten Chicago Bears with the most to prove. Last week, we looked back at the 2025 list, how those players performed, and how that impacted them moving forward. You can see that list here. Several factors go into this list. Is the player […]

NFL

Chicago Bears Post June 1st Trade Roundtable Thoughts – Part 1

We have reached the point during the NFL offseason where a significant increase in trades can and will be processed around the league. This is all due to the Post June 1st designation these trades will have which enables NFL teams to spread out the dead cap charge on veteran players and their contracts for […]

NFL

The Bear’s Den, June 1, 2026

THE DAILY SPONGIE SPECIAL BEARSSSSSS Ken’s Note: Look for stories on WCG specifically about the stadium. The Den is put to bed hours before the session closes, so there may well be late-breaking news. Bears’ Illinois solution hinges on new plan to create local stadium authorities Pre-deadline story. Illinois lawmakers’ fourth-down play to save Bears […]

Chicago Bears Over/Under Player Milestone Predictions (Part 2)

Hello, Chicago Bears fans! Today, we continue the installment of articles this offseason, where I look at benchmarks/milestones for individual Chicago Bears players in the 2026 season and give my prediction on whether they will overachieve or underachieve those benchmarks. Today, we will look at our next five over/under scenarios for the Bears’ individual achievements:  […]

NFL

Chicago Bears 2026 Offseason Superlatives: Make-Or-Break Year

This WCG roundtable series was inspired by this Tweet from our guy Jacob, who gave six 2026 Chicago Bears superlatives for the offseason. We’re going to take them one by one, and we’ll give a couple two tree sentences for each of our choices. Next up is the Bears player who is facing a make-or-break […]

NFL

Is Caleb Williams the Madden 27 cover athlete?

As of this writing, there has never been a Chicago Bears player to grace the cover of EA Sports’ Madden NFL video game franchise. It appears that might soon be changing. MUTLeaks, a popular college football gaming profile on Twitter/X with over 125,000 followers, posted pictures of what appeared to be the leaked covers of […]

Chicago Bears 2026 Offseason Superlatives: Most Underrated

This WCG roundtable series was inspired by this Tweet from our guy Jacob, who gave six 2026 Chicago Bears superlatives for the offseason. We’re going to take them one by one, and we’ll give a couple two tree sentences for each. We already did the Bears’ best player, yesterday was the Bear we’re most excited […]

NFL

‘Expect another exponential jump’ from the Chicago Bears’ offense

The vibe coming out of Halas Hall right now is mostly positive about the Chicago Bears, and I’m not just talking about the Bears’ social media team hyping the squad. The local beat has been more glass-half-full, and the national media has been optimistic all offseason. I get it’s just May 29, and we’re talking […]

Chicago Bears 2026 Offseason Superlatives: Most Excited to Watch

This WCG roundtable series was inspired by this Tweet from our guy Jacob, who gave six 2026 Chicago Bears superlatives for the offseason. We’re going to take them one by one, and we’ll give a couple two tree sentences for each. Yesterday we did the Bears’ best player, and today is the Bear we’re most […]

The Bear’s Den, May 29, 2026

THE DAILY SPONGIE SPECIAL BEARSSSSSS Bears stadium bill in the balance as Springfield session winds down Politicians are the Devil. The Bears’ tenacious rushing attack keyed their offense last season. Recapturing that will be a challenge. Most things in the NFL are. Ben Johnson: Bears QB room in ‘different place than it was a year […]

How far did Caleb Williams throw it? (Wrong answers only)

By now, you’ve all seen the Caleb Williams throw to Rome Odunze from Thursday’s OTA at Halas Hall. If you missed it by chance, here you go, courtesy of the Chicago Bears. Sure, it’s just practice. And okay, it’s not even a live scrimmage. But that clip has people feeling some kind of way. Here […]

Bears’ Jaylon Johnson Attends Voluntary OTAs

Last week, it was reported that Chicago Bears cornerback Jaylon Johnson wasn’t in attendance for the early voluntary Phase of workouts at Halas Hall. This isn’t anything new for Johnson, as he regularly spends the offseason working out at home while spending time with family, but once the mandatory portion of the offseason came around, […]

Ben Johnson: “I’m Buying Luther Burden Stock Right Now”

The Chicago Bears’ offseason training activities (OTAs) are in full swing and Head Coach, Ben Johnson, was tasked with speaking to the media at Halas Hall today to address some off the lingering storylines with his team. Among the most notable has been the success of the 2025 rookie class (at least on offense) and […]

NFL

Chicago Bears 2026 Offseason Superlatives: Best Player

This WCG roundtable series was inspired by this Tweet from our guy Jacob, who gave six 2026 Chicago Bears superlatives for the offseason. We’re going to take them one by one, and we’ll give a couple two tree sentences for each. First up, who we believe is the Bears’ best player. Jacob Infante: Joe Thuney […]

NFL

The Bear’s Den, May 28, 2026

THE DAILY SPONGIE SPECIAL BEARSSSSSS Chicago Bears Coordinator Expects Rookies to Play Big Role on Special Teams As do we all. Veteran Chicago Bears Player Named Trade Candidate for 2026 To the surprise of nobody. Bears Have 4 Reasons to Ignore the Year 2 Regression Warnings Regression warnings are piling up on the Bears, but […]

NFL

What offensive changes can we expect from the Chicago Bears in 2026?

Ben Johnson’s offense in year one with the Chicago Bears was different than what he did with the Detroit Lions. Sure, there were similar concepts he carried over, and his running game was again among the league’s best, but building a playbook around Caleb Williams is different than building one for Jared Goff, which is […]