Eagles vs Bears Prop Picks: Monday Night Football

Jason Logan: Senior Betting Analyst at Covers
Jason Logan • Senior Betting Analyst 21+ years betting experience
Updated: Sep 27, 2026 , 09:00 PM ET • 4 min read

The Bears are without their star QB, and that not only shakes up their offense but also dictates how Jason Logan handicaps the player props for Monday Night Football. Here are his top choices for Eagles vs. Bears.

Philadelphia Eagles wide receiver Dontayvion Wicks NFL.
Photo By - Reuters Connect. Philadelphia Eagles wide receiver Dontayvion Wicks.

Caleb Williams is missing from the Chicago Bears offense, adding a twist to their Monday Night Football clash with the Philadelphia Eagles. 

My Eagles vs. Bears props peel back the layers to this prime-time pairing, giving you my best NFL picks for Sept. 28.

Best Eagles vs Bears props

For help understanding Kalshi probabilities, see our odds calculator.

Pick Kalshi
Probability
 Eagles Dontayvion Wicks 40+ receiving yards 54%
 Bears Kalif Raymond 25+ receiving yards 51%
 Bears D’Andre Swift 2+ receptions 53%

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Prop pick #1: Dontayvion Wicks 40+ receiving yards

Kalshi probability: 54%

The Philadelphia Eagles will see mostly man coverage from the Chicago Bears defense (runs man at the highest rate) on Monday Night Football. 

Eagles WR1 DeVonta Smith is awesome in one-on-one but won’t get too many of those opportunities, with Chicago sending double coverage at his deep-threat ability.

That means WR2 Dontayvion Wicks will see more single coverage, and he’s almost as dangerous in those opportunities. He rates 16th against man coverage at PFF to start the 2026 season and could draw coverage deep down Chicago's depth chart, with the secondary missing bodies.

Wicks has been excellent in his first two games for Philly, posting 73 and 74 yards while catching a collective seven of 10 balls his way. Projections for MNF lean toward 40+ receiving yards with a ceiling of 50+.

Prop pick #2: Kalif Raymond 25+ receiving yards

Kalshi probability: 51%

Caleb Williams’ injury takes away the deeper passing game for the Bears, which makes for a busy day for slot receiver Kalif Raymond. Whichever backup QB is under center, short safe passes will be in the playbook.

That could work well, considering the Eagles have trouble with slot receivers. Philadelphia has allowed the second-most fantasy points to the position through two weeks. Raymond has put up 40 and 84 yards in the first two outings, catching 13 of 14 targets.

His Week 3 models come in north of 30 yards, with highs of 40+ receiving yards.

Prop pick #3: D’Andre Swift 2+ receptions

Kalshi probability: 53%

As mentioned, the Bears passing playbook will be shortened with Williams sidelined. On top of that, this Eagles pass rush won’t leave much time for deeper plays to develop.

Running back D'Andre Swift drew six targets in a wet and windy game against Minnesota last week, in which downfield looks were challenging. He'll be a popular target on designed screens and as a check-down option on Monday.

Most projections sit at 2+ catches for Swift, with some models flirting with three receptions.

Jason Logan's 2026 Transparency Record
  • Prop picks: 11-7, +4.03 units
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Jason Logan Senior Industry Analyst Covers.com
Senior Betting Analyst

In his 20 years with Covers, lead NFL betting analyst Jason Logan has seen it all and bet it all. Through the wild west of early Internet gambling to lobbying for legalized sports betting to our brave new wagering world, Jason has been a consistent source of actionable info and entertainment for squares and sharps alike.

Since joining the Covers team back in 2005, he honed his handicapping skills to provide audiences with the most thorough insights, blending traditional capping methods with advanced modelling and predictive analysis. Jason has studied the ins and outs of the sports betting business, learning from some of the most successful gamblers in the industry and the biggest sportsbook operators on the planet.

He is under center for Covers during NFL season as our top NFL expert, taking the points in his infamous NFL Underdogs column and representing the Covers Community at the Super Bowl. While he lives for football season, Jason's first love is basketball and that shows in his in-depth NBA, NCAA, and WNBA betting breakdowns.

On top of being a mainstay in media from coast to coast at stations like WPIX, PHL17, Fox 5 San Diego, WGNO, TSN, SportsNet, ESPN Radio, Jason's analysis has also been featured in USA Today, MSNBC, ESPN, the Wall Street Journal, CBS, Bloomberg, the L.A. Times, the New York Times and other major publications. You can also find JLo stuffing all the top picks and predictions he can into 10 minutes as the host of Covers' flagship podcast, The Sharp 600.

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