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Windy City Gridiron

https://www.windycitygridiron.com/ | 764 entries published

A Chicago Bears community

Latest Entries

Rivalries Revisited: Checking in on the Teams We’ve Loved to Hate

This summer, I took the opportunity to survey the landscape of Chicago Bears rivalries entering the 2025 NFL season. This included a ranking of the team’s (or fanbase’s) ten biggest rivals, with three honorable mentions thrown in for good measure: My ranking took a number of factors into consideration, but now that the we are […]

3 months ago | 2 reads

Gridiron Time Machine: 5 Bears Week 9 Flashbacks

1.) 2005, Bears @ Saints: Bears beat the Saints at Tiger Stadium for their first 4 game win streak since 2001 In the aftermath of Hurricane Katrina, which tore off nearly 70% of the Superdome’s roof and forced the Saints to play their “home games” across three different stadiums, including LSU’s Tiger Stadium, Kyle Orton […]

3 months ago | 2 reads

Chicago Bears Fan Confidence Survey Results Drop 30%

One week ago, our fanbase was still riding high after watching the Chicago Bears win a fourth straight game. According to our Reacts survey, our confidence in the franchise was 96%. Also, only 7% of our fans believed this 2025 version of the team is still the “same old Bears.” So things were looking up. […]

3 months ago | 2 reads

Chicago Bears at Cincinnati Bengals: 3 Props to Play

The Chicago Bears look to get back in the winning column after dropping one last week to the Baltimore Ravens. Their opponent is the Cincinnati Bengals, who have a porous defense and give us some interesting opportunities to bet on Chicago Bears players on props. Last year, we published after Lamar Jackson was a “full […]

3 months ago | 2 reads

Bears vs. Bengals: Keys to a victory

The Cincinnati Bengals have a lot of firepower on their offense, while the Chicago Bears are reeling defensively due to injuries. It’s a battle of strength versus weakness in a lot of ways this weekend and it’s going to be a tough match up for the Bears to get a win on the road. But […]

3 months ago | 12 reads

Bears Big Plays Tracker Week 8

Modern football is all about big plays and as a companion piece to the STEP Differential, I’m tracking the Bears big plays all year in this Infogram: Chicago Bears 2025 STEP Differential TrackerInfogram Last year’s tracker is on the second page. Remember that you can click into the tabs on the lower left to see […]

3 months ago | 1 read

Updated QB Rankings: Midseason Edition

As we continue with our quarterly QB rankings for the year, we have reached the midseason edition. Before we dive into the rankings, I want to talk about the process of how these rankings are determined. First of all, there’s no equation, there’s no chart, it’s my eye test. Now, certainly, statistics come into play, […]

NFL

3 months ago | 1 read

5 Questions with Cincy Jungle: Can the Bears bounce back?

The Chicago Bears had the magic run out on Sunday with a bumpy loss to the Baltimore Ravens. How will the team rally against a Cincinnati Bengals team that is certainly beatable without Joe Burrow? We sat down with Anthony Cosenza from Cincy Jungle, SB Nation’s Cincinnati Bengals site, to get the Bengals’ perspective on […]

3 months ago | 2 reads

Benchmarking Da Bears: Week 8

The Bears found themselves in unfamiliar territory as they rode the wave of a 4-game winning streak entering a matchup with the struggling Baltimore Ravens this past week. Despite the contrast in team records and the absence of Lamar Jackson, Baltimore was still viewed as the betting favorite in this game. On one hand, this […]

3 months ago | 2 reads

A Halloween Bear’s Den, October 31, 2025

WE WANT YOU! Would you like to show your Chicago Bears spirit to the world? I’m starting a feature where Windy City Gridiron readers can share pictures of themselves and their families and friends in Bears attire. Simply email a picture to me at the following address: denmasterken at aol dot com. The pictures need to be […]

3 months ago | 2 reads

Bears vs Bengals: Complete Week 9 Live Story Stream Coverage

The Chicago Bears are back on the road this Sunday for another AFC North matchup, and hopefully, this one is better than the last one. Much like the Ravens were a week ago, the Cincinnati Bengals are also missing their Pro Bowl quarterback. But as we just saw in Baltimore — on any given Sunday […]

3 months ago | 3 reads

Week 9 NFL TV Schedule: Thursday Night Football Open Thread

We’re up to Week 9 of the 2025 NFL season, and this will be your open thread to talk about all the games. For the TV broadcast maps to determine if these games are on in your local market, check out 506sports.com. Here’s the full slate of games this week (all times Central). Thursday Night […]

NFL

3 months ago | 0 reads

Bear Bones: Getting you ready for Bears vs Bengals

We have a brand new Bear Bones podcast with host Dr. Mason West previewing all the latest about the upcoming Chicago Bears vs the Cincinnati Bengals game. For a third week in a row, the Bears have a lengthy injury list, so Mason will give his best guess on whether the players will play and […]

3 months ago | 2 reads

Should the Bears trade for former Dennis Allen-coached star Marshon Lattimore?

An article from ESPN yesterday suggests the Chicago Bears should be buyers before next Tuesday’s 4 pm (ET) trade deadline, and one voice is suggesting an unconventional addition to the squad. Though Chicago has few truly glaring positions of need offensively, the defense could use some help, especially up front. But Benjamin Solak floated a […]

3 months ago | 2 reads

Silvy: I don’t believe in Ryan Poles

The latest Bears Banter Podcast has dropped! The Chicago Bears sit at 4-3 after dropping a rough one to the Tyler Huntley-led Baltimore Ravens. To talk about where the Bears are at seven games into Ben Johnson’s tenure, we sat down with Marc Silverman! Yes, Silvy of ESPN 1000’s Waddle and Silvy stopped by the […]

3 months ago | 1 read

Week 9 game preview: Bears vs. Bengals

The calendar is turning to November and it’s time for teams to really separate themselves. Teams that are going to make a run at the playoffs have to start playing well. The teams that aren’t, are going to shift into “who do we fire?” and “how high will the draft pick be?” mode. Thankfully, the […]

3 months ago | 2 reads

Caleb Williams Week 8 QB Grade: Bears @ Ravens

Edit [10/30/2025 8:45AM]: Total scoring has been updated, due to a miscalculation in my spreadsheet not counting the turnover as -1.00 and updating the second intentional grounding. Overall grade has dropped to 1.65, which is still firmly an Average grade. As the saying goes, all good things must come to an end. And end it […]

3 months ago | 1 read

The Bear’s Den, October 30, 2025

WE WANT YOU! Would you like to show your Chicago Bears spirit to the world? I’m starting a feature where Windy City Gridiron readers can share pictures of themselves and their families and friends in Bears attire. Simply email a picture to me at the following address: denmasterken at aol dot com. The pictures need to be […]

3 months ago | 6 reads

Bad, Worse, Worst: Chicago Bears vs. Baltimore Ravens

Hello, Chicago Bears fans!  Well, we all knew this day would come.  It can’t be all rainbows, sunshine, and good, better, best in the modern NFL.  Sometimes you win ugly, and sometimes you lose ugly.  And this was an ugly loss for the Chicago Bears against a Baltimore Ravens team featuring a backup quarterback that […]

3 months ago | 3 reads

5 Bears scouting reports from loss to Ravens

The Bears’ four-game winning streak came to an end on Sunday, as they fell 30-16 to a Ravens team without Lamar Jackson to drop their record to 4-3. The flashbacks to last year are natural, seeing as though last year’s Bears started at 4-2 and proceeded to lose each of their next ten games. As […]

3 months ago | 2 reads

Bears Over Beers: Bounce-Back Game vs. Bengals?

Welcome to the latest episode of Bears Over Beers! This week, join our hosts Ryan Droste and Bryan Orenchuk as they as they get you ready for week nine of the 2025 Chicago Bears season! Grab a cold beverage and join Ryan and Bryan as the guys wrap up discussion on the Bears/Ravens game before looking ahead […]

3 months ago | 2 reads