A Week 15 loss to the Green Bay Packers coupled with the Minnesota Vikings beating the Los Angeles Chargers later that day eliminated them from playoff contention.

[35] Two days after their 2018 season ended, on January 8, the Bears signed ten players to futures/reserve contracts, nine of whom were part of the practice squad in 2018: running back Ryan Nall; offensive lineman Dejon Allen; defensive tackle Abdullah Anderson; linebacker Josh Woods; defensive backs John Franklin III, Cyril Grayson, Michael Joseph and Jonathon Mincy; and Canadian Football League player James Vaughters, who last played for the Calgary Stampeders.

[36] Later in the month, Chicago signed receiver Jordan Williams-Lambert and linebacker Jameer Thurman—also CFL players—New Orleans Saints offensive tackle Cornelius Lucas and Tulsa kicker Redford Jones.

[47] On April 12, kicker Elliott Fry, who was a member of the Alliance of American Football's Orlando Apollos until the league's shutdown ten days prior, was signed to a three-year deal.

[25][33] On March 28, running back Jordan Howard, who struggled to adapt to Nagy's offense as he recorded a career-worst 935 rushing yards and nine touchdowns in 2018,[53] was traded to the Philadelphia Eagles for a conditional sixth-round pick in 2020.

[63] Following the draft, the Bears signed 22 undrafted free agents: receivers Emanuel Hall (Missouri) and Thomas Ives (Colgate); tight ends Ian Bunting (California), Dax Raymond (Utah State) and Ellis Richardson (Georgia Southern); offensive linemen Alex Bars and Sam Mustipher (Notre Dame), Blake Blackmar (Baylor), Joe Lowery (Ohio) and Marquez Tucker (Southern Utah); defensive linemen Daryle Banfield (Brown), Jonathan Harris (Lindenwood) and Lawrence Marshall (Michigan); linebackers Mathieu Betts (Laval) and Chuck Harris (Buffalo); defensive backs Jomon Dotson (Nevada), Clifton Duck (Appalachian State), Doyin Jibowu (Fort Hays State), Adarius Pickett (UCLA) and Josh Simmons (Limestone); kicker John Baron II (San Diego State); and long snapper John Wirtel (Kansas).

[98][99] Chuck Pagano’s return to Indianapolis was largely overshadowed by reports of Colts starting quarterback Andrew Luck's retirement, sparking boos in Lucas Oil Stadium after the game.

[101] After trailing 17–7, Chicago scored 20 unanswered points starting with Piñeiro's 58-yard field goal, followed by Vaughters forcing Phillip Walker to fumble on a sack, with Joel Iyiegbuniwe returning the loose ball 22 yards for a touchdown.

Iyiegbuniwe and Doyin Jibowu then recorded a sack and interception on consecutive defensive stands, while Tyler Bray threw a 17-yard touchdown pass to Jesper Horsted as the Bears won 27–17.

[106] A day after the Bears' game against the Colts, during which offensive linemen T. J. Clemmings and Rashaad Coward suffered injuries, Tommy Doles was claimed off waivers from the Atlanta Falcons, marking Chicago's third transaction involving the lineman.

[108] On August 31, the Bears reduced their roster to 53 players by releasing 34 players: Bray, Caldwell, Doles, Duck, Horsted, Jibowu, Vaughters, Daryl Banfield, Alex Bars, Mathieu Betts, Jonathan Bullard, Ian Bunting, Jalen Dalton, Stephen Denmark, Kylie Fitts, John Franklin III, Tanner Gentry, Marvin Hall, Chuck Harris, Jonathan Harris, Thomas Ives, Michael Joseph, Joe Lowery, Jordan McCray, Jonathon Mincy, Taquan Mizzell, Sam Mustipher, Ryan Nall, Ellis Richardson, Jameer Thurman, Marquez Tucker, Joe Walker, Jordan Williams-Lambert and John Wirtel.

[115] Although the defense recorded five sacks,[116] Chicago's offense only ran 15 times as Trubisky attempted 45 passes, the latter of which head coach Matt Nagy assumed responsibility during a Friday press conference.

[128] Before the game, tight end Bradley Sowell was released and Anderson was promoted to take his roster spot; the move came after defensive tackle Bilal Nichols broke his hand in Week 2.

He was also the first Bears player to accomplish the feat in the Super Bowl era,[135][136] and the fourth in team history to do so in one quarter after Red Pollock (1935), Frank Minini (1948) and Gale Sayers (1965).

The next two series ended with punts before Vikings receiver Stefon Diggs was stripped by Prince Amukamara and Clinton-Dix recovered the fumble; the play was initially ruled an incomplete pass before Nagy challenged and successfully overturned the call.

Following four further punts,[143] Dalvin Cook scored on a two-yard touchdown run with 2:58 remaining in the game, but Amukamara tackled Diggs' attempted screen pass on the two-point conversion.

[150] Early in the third quarter, Derek Carr's pitch to Jacobs went wide and was recovered by Mack at the Raiders' 14-yard line; the Bears capitalized with Montgomery's one-yard touchdown run.

When Chicago forced another Oakland fourth down, Cohen returned the ensuing punt a career-best 71 yards to set up Daniel's 16-yard touchdown to Robinson that gave the Bears the 21–17 lead.

[194] Despite early defensive success as the Bears forced two Rams turnovers via Clinton-Dix recovering Todd Gurley's fumble and Smith intercepting Jared Goff, Piñeiro missed 48- and 47-yard field goals and the offense turned the ball over on downs.

[199] Running back Jeremy McNichols, who bounced between various NFL teams since his career began in 2017, and outside linebacker Dewayne Hendrix, who spent the 2019 offseason as an undrafted rookie with the Miami Dolphins, were added to the practice squad.

[210] With Stafford and Driskel both out, third-string quarterback David Blough—who had no NFL regular season experience—assumed starting duties for the Lions,[211] and threw a 75-yard touchdown to Golladay on his team's third offensive play after Amukamara relinquished his coverage to a safety who was not present.

[212] In the second quarter, the Bears had a 59-yard drive that was marred by penalties to result in a first-and-32; it subsequently ended with a turnover on downs, which led to Prater's 25-yard field goal to put Detroit up by ten points.

The next three drives of the game resulted in punts before Montgomery was stripped by Joe Thomas and Jaylon Smith recovered; the Cowboys capitalized on the takeaway with Elliott's two-yard score to start the fourth quarter.

[219] To take his place, the Bears signed linebacker Devante Bond, a former Buccaneer who played four games for Tampa Bay in 2019 but was suspended early in the season for violating the NFL's performance-enhancing drugs policy.

To take Joseph's spot on the practice squad, the team signed wide receiver Alex Wesley, who spent the 2019 offseason with the Giants before being waived from injured reserve in September.

Chicago attempted to improve in the second half as the offense reached the Chiefs' four-yard line, but Trubisky's fourth-down pass to Robinson was broken up by Charvarius Ward.

With the Vikings locked into the sixth playoff seed, they elected to deactivate various starters including linebacker Eric Kendricks and offensive tackles Riley Reiff and Brian O'Neill.

On the Bears' opening second-half drive, the offense focused on rushing as all but one of their nine plays was a run by Montgomery or Nall (the exception being a ten-yard pass by Trubisky to Ridley).

[240] After the Vikings punted and the Bears turned over the ball on downs when Trubisky's sneak failed, Boone recorded a one-yard touchdown run to start the fourth quarter.

[243] The offensive line also struggled in numerous fields including injuries to Long and Massie, a failed position swap between center Whitehair and guard Daniels, and penalties; by season's end, the Bears suffered 43 sacks (12th most in the league) and averaged just 91.1 rushing yards per game (sixth worst).