Windy City Gridiron
It’s topic two of our Bears 2025 schedule roundtable series
We continue our Chicago Bears roundtable series about their 2025 schedule, and here’s question number two.
What is the hardest stretch of games on the Chicago Bears’ schedule?
Give us your answer after checking out what we had to say here.
Jeff “JB” Berckes: A stretch is at least three games, so for me it’s at Vikings, home against the Steelers, at Eagles, at Green Bay. It’s also in the third quarter of the season when this team should have the kinks ironed out. That’ll be a great stretch to cover.
TJ Starman: Weeks 11 - 14 looks to be the toughest to me with at Minnesota, home vs Pittsburgh, at Philadelphia, and at Green Bay all looking like realistic losses in the thick of the season.
Josh Sunderbruch: Week 11 to Week 14 seems brutal, with three away games including the defending champs and two divisional rivals.
Sam Householder: There are two stretches that concern me: Nov. 16 to Dec. 7 when they go at MIN, vs. PIT, at PHI and at GB, but don’t sleep on the Oct. 19 to Nov. 9 stretch with two bad teams (NO, NYG) on either side of two playoff-caliber teams (CIN, BAL). We’ve seen Bears teams screw up spots like that in the past and have it derail a season.
Dr. Mason West: The Bears have seven away games between weeks 4 and 14. There are very winnable games in there, but the travel can be brutal.
Bryan Orenchuk: Weeks 13-18 are the hardest stretch for me. On the road against defending champs and rival Packers to start and finish with a second Packers game, road game Sunday night against 49ers, and close out against defending NFCN champ Lions will make or break our season, IMO.
Ryan Droste: It starts in week 13. At Philadelphia on short rest, followed by at Green Bay on Sunday Night Football the following week. Then they get what should be a win against the Browns before finishing with the Packers, 49ers, and Lions. Brutal.
Lester A. Wiltfong Jr.: I think the Bears could be feeling pretty good about themselves after the first four weeks, so how they maintain focus following the bye in Washington starts a tough stretch. After the Commanders is the Saints, which could be a trap game, because a trip to Baltimore follows, and then in week nine, they’re in Cincinnati.
