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Bears 2023 Schedule: What is the hardest stretch of games?

The WCG crew gives their pick for the toughest stretch of games on the Bears' 2023 schedule.

NFL: Chicago Bears at Detroit Lions Lon Horwedel-USA TODAY Sports

This set of Windy City Gridiron Roundtable topics is all about the Chicago Bears’ 2023 schedule, but before we get into what we said, here’s a refresher on Chicago’s regular season schedule.

What is the hardest stretch of games for the Bears this season?

Robert Schmitz - The start of the season looks really difficult, and I wish it didn’t — playing the Packers early has been an Achilles heel for many Bears seasons, and then they play 4 straight talented defensive lines (among them, the defending Super Bowl champions and the new-look Denver Broncos). I’d love to see the Bears come out of that stretch with a winning record, but that’s a lot of bad matchups early.

Peter Borkowski - There is a scenario the Bears start off 0-4 because of their week 1-4 stretch. We will get our first peek at the new-look Packers in week one, and while there are more questions than ever surrounding that team following his departure, it is still a more proven roster/coaching staff than the Bears, so a week one loss to the Pack is not out of the question, especially if Jordan Love actually looks decent. Tampa Bay is in a similar situation to Green Bay. Yes, their franchise QB is gone, but the Bucs are still a talented team, especially on the defensive end. Kansas City is, well, Kansas City, and Denver should look much-improved thanks to the addition of a legitimate coach (and hopefully a competent Russell Wilson). To be fair, all four of these games besides K.C. are fairly winnable, but if the Bears come out .500 or better, color me impressed.

Jeff Berckes - Weeks 8-12. Four out of five on the road with a home Thursday Night Football game sandwiched in the middle. The Chargers should compete for a playoff spot in a stacked AFC, the Saints are the favorites to win the NFC South, an important game on a short week against the Panthers, and divisional road games against the betting favorite Lions and last year’s winners in Minnesota. All before another late bye week, so the team could be running on fumes.

Sam Householder - Weeks 8-12, basically the entire month of November, looks rough with four of five on the road. A short week going into the only home game and three primetime, nationally televised games. The Panthers might not be good, but the Lions and Chargers have expectations for good seasons, and the Saints are usually tough at home even if they’re trending down.

Lester A. Wiltfong Jr. - Weeks 10 through 13 starts on a short week against a Carolina team whose number one draft pick the Bears hold. That will be a talking point the players and coaches won’t be able to avoid, thus adding extra pressure to win. After that, it’s three straight NFC North contests.

Josh Sunderbruch - Week 11-13 looks rough. With those two away games against division rivals, they could go three weeks without a win.

Erik Christopher Duerrwaechter - I’m not a fan of having three divisional games in a row between weeks 11-14. Even if it’s the Lions twice and once at the Vikings, and their bye before hosting the Lions at Soldier Field, two out of those three games are on the road. There’s no denying the Lions got much better over recent years, and I’m not sure how I feel about playing them twice within four weeks. Divisional games always have weird moments year after year.

Aaron Leming - The stretch between weeks 11 and 15 will be tough. Luckily they have their bye week sandwiched in between, but four games between the Lions, Vikings and Browns could get interesting, especially with three of those being on the road. They must at least split the division in order to have a shot at the playoffs in mid-to-late December. That stretch could end up deciding whether or not they sneak into the playoffs or not.

What stretch of games do you think is the toughest for the Bears this season?

In case you missed it, here’s our pick for the easiest stretch of games.