[11] The first transactions of the year occurred shortly after the conclusion of the 2016 regular season, on January 3, 2017, when the Bears signed to futures contracts cornerbacks De'Vante Bausby, Jacoby Glenn and Rashaad Reynolds, wide receiver Dres Anderson, running back David Cobb, tackle William Poehls, guard Cyril Richardson and center Cornelius Edison.

[69] A second Division II player, Kutztown Golden Bears offensive lineman Jordan Morgan, was drafted with Chicago's final pick (a fifth-rounder and the 147th-overall selection); the first Kutztown player to be drafted since Andre Reed in 1985, Morgan started 43 of 44 games with the Golden Bears, winning the 2016 Gene Upshaw Award and being named the Pennsylvania State Athletic Conference Eastern Division Offensive Athlete of the Year, the first lineman to receive the honor.

[87] A day later, during a practice, guard Eric Kush tore a hamstring from its bone, forcing the Bears to place him on the injured reserve list and rendering him out for the 2017 season.

[92] Against the Broncos, the Bears' preseason started on a rough note; on the third play of the game, Mike Glennon's pass for Zach Miller was intercepted by Chris Harris Jr. and returned 50 yards for a touchdown.

After the Broncos punted to start the second half, Trubisky guided the Bears on a 75-yard series, which ended with Benny Cunningham's one-yard touchdown run to take the 14–10 lead.

[93] Despite the seven-point advantage, the Broncos scored 14 unanswered points on Kyle Sloter's 47-yard touchdown pass to Isaiah McKenzie and DeAngelo Henderson's 41-yard run on third down-and-22 with less than two minutes in the game.

[96] During the resulting drive, J. J. Nelson was stripped by Quintin Demps and recovered by the Bears' Cre'Von LeBlanc, who returned the fumble 77 yards for the score, though it was overturned upon official review and Arizona retained possession of the ball.

On the final play of the first half, Cardinals kicker Phil Dawson attempted a 63-yard field goal, which fell short and was caught by Deonte Thompson, who returned it 109 yards for the touchdown.

In the second half, the Browns scored 18 unanswered points: Zane Gonzalez kicked a 53-yard field goal, Calvin Pryor and Karter Schult sacked Shaw in the end zone for a safety, and Kevin Hogan threw 51- and 21-yard touchdown passes to Randall Telfer and Jordan Leslie, respectively.

Rookie running backs Tarik Cohen and Taquan Mizzell, both players with high agility, were recommended by Gabriel for use, as "gimmicks" are more effective at the start of the season due to a lack of preparation for them.

Cohen later took a direct snap from the center in the Wildcat formation and handed the ball to Jordan Howard, who received assistance on a block by Glennon to score a five-yard touchdown.

Down by six with 3:21 remaining in the game, Glennon drove the Bears downfield and reached the Falcons' five-yard line, but his first three passes to Josh Bellamy, Howard, and Miller fell incomplete.

Defensively, Joniak wrote the Bears had "their hands full" as Steelers quarterback Ben Roethlisberger was aided by receivers Antonio Brown and Martavis Bryant, running back Le'Veon Bell, and tight end Jesse James.

After winning the coin toss to start overtime with the ball, the Bears quickly scored on the second play of the series;[118] Tarik Cohen broke through for a 73-yard touchdown run, but was ruled to have stepped out of bounds at the Steelers' 37-yard line.

On Monday Night Football, Mitchell Trubisky made his NFL debut against the Minnesota Vikings, who led the all-time series 58–52–2, though the Bears had won all but two games at Soldier Field since 2007.

With 2:32 remaining in the game and pinned at his team's ten-yard line, Trubisky's pass for Miller was intercepted by Harrison Smith, which set up Forbath's game-winning 26-yard field goal with 12 seconds to go.

However, Tucker kicked a 50-yard field goal with 2:53 remaining, while Michael Campanaro scored on a 77-yard punt return touchdown and Flacco completed the two-point conversion to Nick Boyle to tie the game at 24 apiece and enter overtime.

Aided by Trubisky's 46-yard run, Tarik Cohen dove into the end zone from the Saints' one-yard line to score the offense's first touchdown in 25 series (dating back to the Baltimore game).

Jeff Joniak described his ideal Bears offensive gameplan as "[p]laying a clean game" to avoid swinging the "tempo or momentum in favor of a team that's on a three-game losing streak."

'"[159] The Bears offense made early progress on the opening drive as it reached the Lions' five-yard line before stalling and settling for Connor Barth's 23-yard field goal.

On Detroit's first series, Matthew Stafford was sacked by Nick Kwiatkoski and fumbled, with Hicks recovering the ball; the Bears capitalized on the takeaway via Jordan Howard's 50-yard run and Trubisky's one-yard touchdown pass to Adam Shaheen.

With Danny Trevathan and Leonard Floyd out due to injuries, the backups were also challenged by a rushing unit featuring LeGarrette Blount and Jay Ajayi, which ranked second in the NFL.

Later in the first half, Jake Elliott made a 45-yard field goal to increase the gap, and Wentz threw an eight-yard touchdown pass to Alshon Jeffery with five seconds remaining to make the halftime score 24–0.

While the Bears punted on their first drive,[170] Kyle Fuller recorded his first interception since 2015 when he yanked the ball from Louis Murphy's hands, which set up Mitchell Trubisky's eight-yard touchdown pass to Dontrelle Inman.

[170] Early in the fourth quarter, Cohen returned a punt for 67 yards to the 49ers' 16-yard line, but Ben Braunecker was penalized for an illegal block in the back to negate the play and force the Bears to start at their own 14.

[172] On defense, the Bears had to play without players like Pernell McPhee, Leonard Floyd, Eddie Goldman, Willie Young, Mitch Unrein, Jerrell Freeman, Adrian Amos, and Quintin Demps, all of whom were sidelined due to injuries.

[173] Early in the second quarter, Mitchell Trubisky threw a 15-yard touchdown pass to Cohen, but it was nullified by Tom Compton's holding penalty; the Bears were eventually forced to settle for Nugent's 34-yard field goal to retake the lead.

The defense entered the game with a fifth-ranked red zone touchdown efficiency, while also excelling in providing pressure, ranking second in sacks on third down, ninth in opposing quarterback rating when blitzed, and leading the league in fumble recoveries with 12.

On offense, protecting Mitchell Trubisky from Gregg Williams' blitz-heavy defense; despite its frequency of utilizing the pass rush, the Browns ranked 29th in quarterback knockdowns with 62, while also allowing ten touchdowns on blitzes.

A series later,[183] Rashard Higgins caught Kizer's pass and reached the Bears' three-yard line, where he was stripped by Danny Trevathan and the ball went into the end zone, where Prince Amukamara recovered.