Chicago Bears’ Schedule Implies a Tough Road to the Playoffs

NFL: Chicago Bears Minicamp

Ask any NFL fan who they believe will win the NFC North Division this season, and most will tell you it’s the Packers. Some may say the Minnesota Vikings. None will say the Detroit Lions, and few will say the Chicago Bears.


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It’s not that Chicago had an awful 2020. The Bears went 8-8 during the regular season and made it to the playoffs, falling to the New Orleans Saints in a wildcard contest. 

In many respects, last season was a great one for Chicago. But as good as 2020 was, 2021 could be challenging.

Last year’s starting quarterback, Mitchell Trubisky, is no longer with the team. Not only that, but Chicago has a challenging schedule.

Chicago Bears’ Schedule Implies a Tough Road to the Playoffs
Jun 16, 2021; Lake Forest, Illinois, USA; Chicago Bears quarterback Nick Foles (9) looks to pass the ball during minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-USA TODAY Sports

CBS Sports ranks Chicago’s schedule this season third most difficult in the league. It doesn’t seem fair that a team that barely finished .500 must play the third most demanding schedule.

But that’s the NFL where the league determines out-of-conference and out-of-division foes on a rotating basis. This season the Bears must play teams from the NFC West and AFC North.

Most NFL analysts feel the NFC West could produce four playoff teams. The San Francisco 49ers and Los Angeles Rams are on the shortlist to win the Super Bowl. The Arizona Cardinals and Seattle Seahawks are postseason contenders.

AFC North teams include the Baltimore Ravens and Cleveland Browns, two squads with conference championship hopes. The Pittsburgh Steelers are always a playoff contender.    

Chicago must also face Super Bowl champion Tampa Bay. Any way we cut it, the Chicago Bears 2021 NFL Regular Season schedule poses a challenge. 

Who will the Bears start at quarterback in Week 1?

The first challenge? Deciding on a starting quarterback. Chicago moved from 20th up to 11th to draft Justin Fields.

The Ohio State star may require a couple of seasons before sitting under center, which is why Bears fans should have been but weren’t ecstatic that head coach Matt Nagy signed Andy Dalton before the 2021 NLF Draft. 

Dalton is the consummate pro. The former Cincinnati Bengal will ensure a smooth transition if Fields requires time to develop. Starting Dalton, though, may not help the Bears make the playoffs.

Then again, when it comes to playoff chances, a rookie at quarterback wouldn’t either. So don’t expect Nagy to decide which quarterback will best help the Bears win the NFC North.

Nagy will decide how long he feels it will take for the former Buckeye star to get up to speed. If Nagy believes Justin Fields is ready to go, Fields will start Week 1. 

Jun 16, 2021; Lake Forest, Illinois, USA; Chicago Bears Darion Clark (44) in action during minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-USA TODAY Sports

What games on the schedule must the Bears win to make the NFL Playoffs?

Chicago Bears’ Schedule Implies a Tough Road to the Playoffs
Jun 16, 2021; Lake Forest, Illinois, USA; Chicago Bears Darion Clark (44) in action during minicamp at Halas Hall. Mandatory Credit: Kamil Krzaczynski-USA TODAY Sports

The league added an extra game, which means the regular season lasts for 18 weeks this year. With the added game, Chicago has a chance to get above .500.

Most analysts don’t believe that will happen. The key for any team to get to .500 or beyond rests in their ability to win division games. 

Chicago should have at least two division victories this season. The Detroit Lions won’t field a good ball club. 

Detroit swapped quarterbacks. The Lions got Jared Goff, and the Rams got Matthew Stafford. There isn’t a single NFL analyst who believes Detroit got the better end of the deal. 

To get to .500, the Bears must not only beat Detroit twice, but they must also split with the Packers and Vikings because the rest of the schedule, as we’ve already discussed, is brutal. 

Outside of the game against the Buccaneers, which is more like a dive into a bottomless chasm than a pitfall, the following five games will determine Chicago’s fate.

Remember, we’re starting with four wins, two against the Lions, and a victory against the Vikings and the Packers. We’re also hoping that a 9-8 record is enough to propel the Bears to the postseason.

  • vs. Cincinnati Bengals – Sep. 19
  • at Las Vegas Raiders – Oct. 10
  • vs. Baltimore Ravens – Nov. 21
  • vs. Arizona Cardinals – Dec. 5
  • vs. New York Giants – Jan. 2

The Bears should also circle this year’s Halloween game on Sunday, Oct. 31, against the San Francisco 49ers. Chicago takes on San Francisco at Soldier Field. Winning that game could take off the pressure to win in November and December. 


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Ask for value if you think the Chicago Bears can win the Super Bowl

The Bears are at +300 to win the NFC North crown with both mainstream bookmakers and pay per head bookmakers who provide free sportsbook software. Although the odds give Chicago a chance, both the Green Bay Packers and Minnesota Vikings are favorites over the Bears.

Detroit is the one team that shouldn’t challenge for the division title. Lions management has said they view 2021 as a rebuilding season. 

Why does Chicago offer low odds to win the division? The Bears aren’t the only team in the NFC North facing a daunting schedule.

Green Bay’s schedule ranks fourth in terms of difficulty. Minnesota’s schedule ranks fifth. 

Backing the Bears at +300 to win the division makes some sense. But if Chicago fans are thinking of supporting their favorite team to win the Super Bowl, they should think twice before heading to an online sportsbook.

Bookie software agents, those who provide free betting software, can offer whatever odds they wish. Chicago fans hoping to score the best possible odds on the Bears to pull off a Super Bowl 56 upset should contact a local sportsbook software bookie and ask for their desired odds.    

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