The Bears won their first three games in the regular season against the Cincinnati Bengals, Minnesota Vikings, and Pittsburgh Steelers, before losing in weeks four and five to the Detroit Lions and New Orleans Saints.

[20] On January 28, Chicago hired former Bears safety Chris Harris as defensive quality control, with Sean Desai serving the same position, along with Dwayne Stukes as assistant special teams coordinator.

[38] The Bears acquired free agents Cheta Ozougwu,[39] Brittan Golden,[40] Matt Blanchard, Terrence Toliver,[41] Patrick Trahan,[42] Brody Eldridge,[43] Fendi Onobun, Lawrence Wilson,[44] Cyhl Quarles,[21] Tom Nelson,[10] and LeQuan Lewis[45] in the pre-free agency signing period.

NFL free agency opened on March 12,[46] with the Bears signing New York Giants tight end Martellus Bennett[47] and New Orleans Saints offensive lineman Jermon Bushrod.

[49] Steve Maneri,[50] D. J. Williams,[51] Tom Zbikowski,[52] James Anderson,[53] Matt Slauson,[54] Andre Fluellen, Kyle Moore, Taylor Boggs,[55] Eben Britton,[56] and Austin Signor[57] followed.

[105] Though the Bears retaliated after Blanchard threw a 58-yard pass to Marquess Wilson to Carolina's 4-yard line, followed by Michael Ford's touchdown run,[103] Graham Gano's 50-yard field goal was the final score of the game,[105] as the Panthers triumphed 24–17.

Later, Armonty Bryant forced Harvey Unga to fumble, which was recovered by Cleveland's L. J. Foyt, which led to Spencer Lanning kicking the go-ahead field goal to put the Browns up 18–16.

[152] The Bengals failed to score on the next drive with 6:38 left, and the Bears clinched the game after Rey Maualuga was called for a personal foul after Michael Bush was stopped on third down.

[162] Chicago started the game with Robbie Gould's field goal, followed by Matt Forté and Michael Bush's touchdown runs to take a 17–0 lead in the first quarter.

In the second half, the Steelers began to rally with Roethlisberger throwing two touchdown passes of 33 and 21 yards to Antonio Brown, followed by Suisham kicking two more field goals to narrow the margin to 27–23.

However, after a David Akers field goal, the Lions would score three unanswered touchdowns, all within 3 minutes, 26 seconds: Micheal Spurlock's 57-yard punt return led to Matthew Stafford's 1-yard run, while Jay Cutler was intercepted by Glover Quin, which set up Stafford's 2-yard pass to Calvin Johnson; finally, the Lions scored after Reggie Bush found a hole and hurdled over Bears' safety Major Wright en route to a 37-yard touchdown.

On the ensuing possession, Malcolm Jenkins forced Jay Cutler to fumble, and Cameron Jordan recovered the loose ball and reached the Bears' 6-yard line.

On Washington's ensuing drive, Griffin was intercepted by Charles Tillman, who returned the pick to the Redskins' 10-yard line, which set up Matt Forté's two-yard touchdown run.

Jay Cutler and Lance Briggs were projected to be out for four weeks, while Brandon Marshall, Alshon Jeffery, Charles Tillman, Major Wright and Blake Costanzo, the other five players hurt, used the bye to heal.

[198] Once the Packers got the ball back, Wallace's pass for Jordy Nelson[199] was tipped and intercepted by Julius Peppers, and was returned 14 yards to Green Bay's 45-yard line, but after the Bears failed to convert on third down, Adam Podlesh's punt was blocked by Jamari Lattimore.

In the fourth, Stafford was intercepted by Chris Conte, who reached Detroit's 9-yard line, and Cutler would then throw a 14-yard touchdown pass to Alshon Jeffery, which was eventually nullified.

On the two-point conversion, McCown's pass to tight end Dante Rosario fell incomplete, but Willie Young was penalized for roughing the passer, allowing the Bears a second chance, which failed after Matt Forté was tackled by Nick Fairley in the backfield.

[218] In the second quarter, Robbie Gould kicked a 20-yard field goal,[214] and eventually, rookie defensive end David Bass escaped a chop block by Rice and intercepted Flacco,[219] scoring on a 24-yard return and tying the game.

[218] The Ravens eventually scored on Torrey Smith's five-yard touchdown catch,[214] and after Flacco had a pass intercepted by Jon Bostic, Gould ended the half kicking a 46-yarder.

McCown then completed a 43-yard pass to Martellus Bennett,[219] and Gould kicked the game-winning 38-yard field goal with 8:41 remaining to win the game 23–20, which lasted five hours, 16 minutes.

[224] In the second quarter, McCown threw an incomplete pass, which appeared to be a fumble, and after Rams cornerback Trumaine Johnson picked up the ball, Bears fullback Tony Fiammetta pulled him to the ground by the facemask.

[236] On Minnesota's first possession of the final quarter, Matt Cassel threw an eight-yard touchdown to Greg Jennings, and on Chicago's next drive,[234] McCown's flip pass for Kyle Long was deflected and stripped by Audie Cole, with Marvin Mitchell recovering.

[235] Despite starting the drive in the Bears' red zone and reaching the six-yard line,[234] Cassel's pass for Rhett Ellison was tipped and intercepted by Khaseem Greene.

After Robbie Gould kicked a 27-yard field goal, the Bears scored again after McCown threw a 25-yard touchdown pass to Alshon Jeffery, who caught the ball over B. W. Webb in the back of the endzone[242] with 0:17 left in the half.

[253] Eventually, Cutler guided the Bears from their own 5-yard line, culminating in a 45-yard touchdown pass to Jeffery after Gipson made an ill-timed leap and Julian Posey being unable to interrupt the play[254] with 10:59 remaining.

[266] Defensive coordinator Mel Tucker called a blitz,[268] but Conte failed to apply man-to-man coverage, allowing Cobb to score the game-winning touchdown.

[266] The Bears received the ball with 38 seconds left, and reached the Packers' 45-yard line, where Cutler's Hail Mary pass[270] for Marshall was intercepted by Sam Shields as time expired.

[281] Regarding the defense, Chicago Tribune writer Steve Rosenbloom wrote, "Under Angelo and Smith, the Bears couldn't win enough games where they needed only three offensive touchdowns.

In the other five games, McCown completed 66.8 percent of passes for 1,829 yards, 13 touchdowns, one interception, and a 109 passer rating, which ranked third in the NFL behind Denver's Peyton Manning and Philadelphia's Nick Foles.

[299] Forte, Marshall and Jeffery's invitations also marked the first time since 1985 the Bears sent multiple skill position players, and the most sent by the team since 1963 with Bill Wade, Joe Marconi and Mike Ditka.