[26] On January 29, the Bears signed Calgary Stampeders cornerback Tre Roberson on a two-year deal; the Canadian Football League player won the 106th Grey Cup in 2018 and recorded seven interceptions in 2019.

In addition to re-signing free agents like quarterback Tyler Bray whose practice squad contract expired in January,[8][29] the team signed tight end Jimmy Graham, cornerback Artie Burns and safety Jordan Lucas.

A five-time Pro Bowler, Graham spent the last two seasons with the Packers; Burns was a former first-round draft pick by the Pittsburgh Steelers with four career interceptions; Lucas was a backup for the Kansas City Chiefs as they won Super Bowl LIV.

[36] On January 5, guard Kyle Long announced his retirement on Twitter after playing his entire career with the Bears; he struggled with injuries in his later years, including being placed on injured reserve in 2019.

[41] The Bears entered the 2020 NFL draft with sports outlets generally agreeing they needed help at tight end, offensive line, and defensive back, with quarterback and wide receiver also being positions that could be bolstered.

Kmet, who grew up near Chicago and was a Bears fan during his childhood, caught 43 passes for 515 yards and six touchdowns in 2019, while Johnson was named first-team All-Pac-12 Conference and recorded 36 tackles two interceptions during his final year, but fell from his projected first-round draft grade after undergoing surgeries on his shoulders.

[51] After the draft, the Bears signed 11 undrafted free agents: running backs Napoleon Maxwell (Florida Atlantic) and Artavis Pierce (Oregon State); receiver Ahmad Wagner (Kentucky); guard Dieter Eiselen (Yale); offensive tackle Badara Traore (LSU); defensive tackles Lee Autry (Mississippi State) and Trevor McSwain (Duke); linebackers Keandre Jones (Maryland), Ledarius Mack (Buffalo), LaCale London (Western Illinois), and Rashad Smith (Florida Atlantic).

[60] When Training Camp began on July 28, the Bears implemented pandemic safety protocols that included designating head trainer Andre Tucker as infectious control officer and converting a player's lounge into an additional locker room.

[64] Yet another tight end, 2017 second-round draft pick Adam Shaheen, was traded on July 26 to the Miami Dolphins for a 2021 seventh-round selection; linebacker Devante Bond, Brice, and Wesley were released the same day.

[68] On August 20, Burns was placed on injured reserve after hurting his left knee in practice three days prior; receiver Rodney Adams, who had been on the Indianapolis Colts' reserve/retired list earlier in the spring, was signed.

[76][77] After Training Camp's conclusion, roster cuts to reach the 53-man limit began on September 3 with Maxwell, Wesley and Wagner, offensive lineman Corey Levin, Autry, and Jones.

[79][80] Adams, Anderson, Bray, Crawford, Davis, Denmark, Horsted, Ives, London, Mustipher, Pierce, Santos, Simmons, Smith, Traore were signed to the practice squad on September 6, as was former Atlanta Falcons offensive lineman Jamon Brown.

[90] The two teams traded punts to begin the game; after the Bears turned the ball over on downs in Lions territory, Matt Prater and Santos exchanged field goals of 27 and 35 yards, respectively.

The Lions' momentum continued in the second half when Stafford led a 72-yard drive that culminated in a four-yard touchdown pass to Hockenson, followed by Prater's 44-yard field goal to increase the gap to 23–6.

[91] Chicago's offense, which had struggled early as it failed to convert its first seven third-down situations, rebounded in the fourth quarter as Trubisky threw a two-yard touchdown pass to Jimmy Graham.

[92] The victory was the Bears' first in a season opener since 2013, while the 21 points scored in the fourth quarter were the most in the final period since 2014 against the Dallas Cowboys; it was also Chicago's first fourth-quarter comeback from double digits since a 2015 win over the Kansas City Chiefs.

The Giants punted on their first drive of the second half, but would score 13 unanswered points on their next three possessions:[104] after Trubisky's pass for Robinson was deflected by James Bradberry and intercepted by Julian Love, Gano made a 39-yard kick; a Bears punt led to a 95-yard possession by New York that ended with Dion Lewis' one-yard touchdown run; a second Trubisky interception, this time when Bradberry pulled the ball from Robinson, led to Gano's 37-yarder.

[101] The Bears' last drive of the game ran for 44 yards, including a tipped pass on fourth down that was caught by offensive lineman Bobby Massie, though Santos missed a 50-yard kick with 2:02 remaining.

The Colts answered with two Rodrigo Blankenship field goals of 21 and 30 yards,[124] though the first was set up when Roquan Smith intercepted Rivers in the end zone at the three-yard line but was ruled out of bounds.

[132] The Bears responded with a three-yard touchdown run by Montgomery, the team's first rushing score of the season,[133] followed by Fuller forcing a fumble after hitting Ke'Shawn Vaughn and knocking the ball free, which Quinn recovered at the Buccaneers' 27-yard line.

[135] Guard James Daniels suffered a pectoral muscle injury in the game and was placedo on injured reserve on October 14; practice squad lineman Sam Mustipher was promoted to take his place.

[140] Following a Bears punt to start the second half,[141] the two teams traded turnovers when Mike Davis was stripped by Jackson and Hicks recovered the fumble, but Foles' throw for Harris was intercepted by Jeremy Chinn on the next play.

Although Chicago reached Los Angeles' nine-yard line on the following drive, Foles' pass to Mooney was tipped by Troy Hill and intercepted by Taylor Rapp, which the Rams capitalized on with a 12-yard touchdown throw from Goff to Gerald Everett.

[154] Wil Lutz and Santos traded 38- and 44-yard field goals on their teams' opening drives; the Bears' first series saw a Foles incomplete pass to Montgomery be initially ruled as a fumble recovered by New Orleans' Sheldon Rankins before being overturned and Trubisky briefly return as a Wildcat formation quarterback.

Chicago's offense responded with a 57-yard run by Montgomery to Green Bay's eight-yard line, but he was stopped for a one-yard loss on the next play and two incomplete passes led to Santos' 27-yard field goal.

On his team's 17-yard line, Trubisky was strip-sacked by Romeo Okwara and John Penisini recovered at the Bears' seven, which set up Peterson's five-yard touchdown run to give the Lions the 34–20 lead.

[214][215] Skrine was once again inactive as he remained out with a concussion, while Johnson and Bush respectively hurt their shoulder and foot against Houston and missed the game; the injuries prompted the Bears to elevate Xavier Crawford from the practice squad.

[242] The Bears punted on the ensuing possession, but Demetrius Harris forced Green Bay returner Tavon Austin to fumble and Houston-Carson recovered at the Packers' 20, leading to Santos' 30-yard field goal.

[255] Following another Bears punt to begin the second half, the Saints drove 85 yards—aided by a fourth-down neutral zone infraction penalty on Jackson—and score on Latavius Murray's six-yard touchdown pass.

Further defensive penalties hindered the Bears on the Saints' next possession when Kindle Vildor's holding nullified a 14-yard sack by Mack and Trevathan's pass interference set up New Orleans at Chicago's one-yard line, where Alvin Kamara scored on a run.