The Cowboys (2-1) are coming off a close 16-10 win over the Tampa Bay Buccaneers, in which Rob Ryan's defense allowed just 197 total yards.
Aside from Monday Night Football being one of the greatest NFL spectacles, there are other reasons to tune in to ESPN for the game, and here they are.
Cowboys' Pass Defense vs. Bears' Passing Offense
Cutler and his receivers could be in for a rough night against a surprisingly talented Cowboys secondary that has allowed just 137 passing yards per game through three weeks.
Brandon Carr, Mike Jenkins, Morris Claiborne and Gerald Sensabaugh combine to form one of the most athletic defensive back corps in the league, and it should look even better thanks to Cutler's lock of prime-time football prowess (more on that to follow).
Jay Cutler's Return to Prime Time
Jay Cutler turned in one of the more abysmal prime-time performances of the year against the Green Bay Packers in Week 2, as he went 11-of-27 for 126 yards, one touchdown and four picks.
His quarterback rating of 28.2 isn't indicative of his talent as a quarterback, but it is a testament to how unkind prime time has been to him.
Cutler didn't exactly have a bounce-back performance in Week 3 against a subpar St. Louis Rams team, and he could be in for another rough night against an even better team.
Tony Romo and the Inconsistent Cowboys Offense
Whether you love the Cowboys or love to hate the Cowboys, you have to admit that their offense can be one of the most potent in the league or one of the most anemic.
Make your pick
Romo has been plagued with the tendency to make big mistakes when the Cowboys need him the most. That could be a problem for Cowboys faithful, as this game between top-tier teams is sure to come down to the wire.
In Week 1 against the New York Giants, Romo's offense put up 433 yards of total offense, but it has been held under the 300 mark since then. The Bears are sixth in the league in total defense, so it will be interesting to see how the Cowboys game-plan.