Windy City Gridiron
A Chicago Bears community
Total reads
5,815
This week
11
Rank
#16 of 417
Published
1,621 posts
Most read posts
Featured on Sportsblogs
Run this blog? Add the badge to your site to show readers you're featured — it links back to this page.
Latest Entries
The Bear’s Den, July 7, 2026
Den picture caption: SEATTLE, WASHINGTON – JULY 06: Chicago Bears wide receiver Rome Odunze fulfills his role as the adidas Stadium Captain with the adidas Trionda match ball before the FIFA World Cup 2026 Round of 16 match between USA and Belgium at Seattle Stadium on July 06, 2026 in Seattle, Washington. (Photo by Sarah […]
10 Most Important Bears of 2026: #7 Jaylon Johnson
Last year, the Chicago Bears got only 7 regular-season games from Jaylon Johnson (and both postseason games), but I don’t think he was 100% in any of them. His offseason was hampered by a groin injury, and then during his first game (week 2 vs. the Lions), he suffered a different groin injury, this one […]
Training Camp Battle: LB2: D’Marco Jackson vs TJ Edwards
It’s time to kick off our next yearly off-season series, where we look at interesting training camp battles that could develop throughout July and August. As always, we will unveil these throughout July as we inch closer to the players reporting to training camp. Let’s kick it off on the defensive side of the ball […]
The NFL’s 5 Most Improved (Non-Playoff) Teams That Could Go Worst To First
Of all the professional sports leagues in the country, the NFL boasts one of the highest rates of turnover among playoff teams each year. Each year, we see teams go from worst to first. While many would make the argument that the Los Angeles Rams are the league’s most improved team (on paper), we’ll focus […]
The Bear’s Den, July 6, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS Caleb Williams sends a signed jersey to Chicago native Pope Leo Bears quarterback Caleb Williams has sent a signed jersey to Pope Leo XIV. Leo, born as Robert Francis Prevost, is a Chicago native. And, given that there’s only one NFL team in town, it’s safe to say he’s a Bears fan. […]
10 Most Important Bears of 2026: #8 Grady Jarrett
Despite any expectations fans may have about Grady Jarrett, the Chicago Bears’ lack of significant movement at the position suggests they still expect him to be a difference-maker in the middle of the defense. Oh, sure, they brought in Neville Gallimore on a two-year, $10 million deal, but they needed a replacement for Andrew Billings. […]
The 10 Most Important Chicago Bears of 2026
Our 10 Most Important Chicago Bears list started on July 1, and we’ll gather all the articles here in this storystream over the next week. This is the 18th consecutive year we’ve run this series, and it’s proven to be a good conversation starter in a quiet part of the offseason. Something to keep in […]
America at 250: Founding Fathers Football Squad
It was 250 years ago today that a group of men sat around a table at the Pennsylvania State House in Philadelphia, PA, and signed the Declaration of Independence. It was the birth of an idea and the birth of a country. So let’s have some fun on this 4th of July on our country’s […]
How big a season do you expect from Coby Bryant and Dillon Thieneman?
Earlier this week, we asked you guys to vote on which Chicago Bears defender would lead the team in takeaways, and more than half of you went with newcomer Coby Bryant. After losing corner Nahshon Wright (8 takeaways), safety Kevin Byard (7 takeaways), and linebacker Tremaine Edmunds (6 takeaways) to free agency, the Bears will […]
All-Time Historical Bears Team Tournament: Blue Ridge Better Bests vs Gary’s Bears
In the first round of our 2026 All-Time Historical Chicago Bears Fantasy Draft Tournament, we have Bryan Orenchuk’s (2) Blue Ridge Better Bests vs Gary Baugher Jr.’s (7) Gary’s Bears. Bryan details his team here, and Gary takes a look at his squad right here. Check out each position group in the image sliders below, […]
10 Most Important Bears of 2026: #9 Braxton Jones
I nearly went back to back with a position instead of a player here at number nine (much like center yesterday), but the more I thought about it, the more I realized Braxton Jones is the best case scenario at left tackle for the 2026 Chicago Bears. He was the best case last year, too, […]
The Bear’s Den, July 3, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS Chicago Bears Running Back Room in top 15 Despite boasting the league’s third-best rushing attack and a prolific dual-threat backfield, analysts remain skeptical of the Chicago Bears’ running backs. Caleb Williams retweets Mark Schlereth’s calling Caleb a bad quarterback On Thursday afternoon, the 24-year-old retweeted a clip on X of […]
Should the Chicago Bears try to make this bold trade prediction come true?
Aside from the edge position, there’s one spot on the Chicago Bears roster that, honestly, could’ve used a slight upgrade: running back. Yes, D’Andre Swift and Kyle Monangai were among the best running back duos in the NFL last year, and Swift had a career year in 2025 after struggling in his first Bears season […]
All-Time Historical Bears Team Tournament: Gridiron Greats vs Chicago Monsters
In our 3rd first round matchup of our 2026 All-Time Historical Chicago Bears Fantasy Draft Tournament, we have Lester A. Wiltfong Jr.’s (4) Gridiron Greats vs Donald Gooch’s (5) Chicago Monsters. Lester breaks his team down here, and Gooch spotlights his team right here. Check out each position group in the image sliders below, and […]
10 Most Important Bears of 2026: #10 Center
After the Chicago Bears gave Drew Dalman a big free-agent deal last offseason and he went on to start every game while playing at a Pro Bowl level, I assumed the Bears had finally figured out their center for the foreseeable future. “But not so fast, my friend” Last year, Dalman made my Most Important […]
The Bear’s Den, July 2, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS Caleb Williams: We’ll get the completion percentage up, make everyone feel warm and lovely Bears quarterback Caleb Williams did well enough in the biggest moments to lead the team to a division title and a thrilling playoff win over the Packers last season, but there are still those who feel […]
All-Time Historical Bears Team Tournament: Evil Demons from Hell vs Bear Essentials
In our next first-round matchup of our 2026 All-Time Historical Chicago Bears Fantasy Draft Tournament, we have Jacob Infante’s (3) Evil Demons from Hell vs Josh Sunderbrich’s (6) Bear Essentials. Jacob breaks down his entire team here, and Josh breaks his team down right here. Check out each team’s position group in the image sliders […]
Looking back at my 10 Most Important Chicago Bears of 2025
These annual look-backs at my previous 10 Most Important Chicago Bears lists are often depressing, because before last year, I had only covered three winning seasons as a writer here at WCG (2009-). The majority of the guys on my — these are the most important guys who really need to come through for the Bears […]
Gerald McCoy: ‘Caleb Williams will be the Best QB in the NFL’
Gerald McCoy tormented quarterbacks for a decade in the NFL for the Tampa Bay Buccaneers and Carolina Panthers, earning six Pro Bowls and a First Team All-Pro honor across his impressive career. Anytime an accomplished NFL veteran reflects on current players in the league, it’s worth listening, which is why I was delighted to read […]
Question of the Day: Who will win Chicago’s next championship?
The City of Chicago holds deep pride in its sports teams. This is despite the fact that each franchise within the City has had a history of inconsistent success, at best. However, if anyone has been paying attention recently, Chicago sports may be on the verge of a renaissance. Of the 8 professional sports teams […]
The Bear’s Den, July 1, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS Which Chicago free agent has the most to prove this season? The Chicago Bears made several signings in free agency to upgrade the defense. Which newcomer has the most to prove in Chicago? Chicago Bears Offseason Grades: Did Ryan Poles do enough to fill the team’s biggest needs? Ryan Poles […]
All-Time Historical Bears Team Tournament: Team Sweetness vs Special Bears Unit
In the first round of our 2026 All-Time Historical Chicago Bears Fantasy Draft Tournament, we have Jack M Silverstein’s (1) Team Sweetness vs TJ Starman’s (8) Special Bears Unit. Jack breaks down his entire team here, and TJ’s squad breakdown is right here. Check out each position group in the image sliders below, and then […]
30 Day Challenge: What I’m Most Excited About for the Bears’ 2026 Season
As we inch closer to the start of the Chicago Bears’ 2026 season, the excitement surrounding this team within the fanbase is palpable. It’s one of the few times in recent years that the fanbase has felt this hopeful heading into the upcoming season. And for good reason as there are plenty of reasons to […]
Chicago Bears’ Ben Johnson had the best playcall of 2025
The Chicago Bears battled back and forth with the San Francisco 49ers on December 28th, 2025, in a primetime Sunday Night Football matchup that was a thing of offensive beauty. It featured five ties, 80 points, and 936 yards of offense. The visiting Bears tied the game up at 35 a few seconds into the […]
The Bear’s Den, June 30, 2026
THE DAILY SPONGIE SPECIAL BEARSSSSSS Three Bears on NFL Top 100 list CBS Sports’ Pete Prisco released his top 100 NFL players of 2026, and three Bears made that cut: Colston Loveland (No. 100), Caleb Williams (No. 70) and Joe Thuney (No. 55). Bears Film Study: Ben Johnson Unleashes Vertical Passing Game vs. 49ers Even though […]
Displaying items 1-25 of 1621 in total