The Bears' record fell off slightly, with the team finishing at 11–4 in the strike-shortened season. Their record was once again good enough for the division title and the #2 seed in the conference, as the team had done the year before. The team also saw the same result as 1986 as the Bears suffered a second consecutive loss to the Redskins, who went on to win Super Bowl XXII, in the Divisional Playoffs.
The 1987 season proved to be a frustrating one for not only the Bears, but probably for most associating with professional football. The league endured its second strike-shortened season in the last 6 seasons, and this was a strike that truly divided teams, including Chicago.
In the windy city, the strike divided its players and tarnished its coach, and the season would be the last for greats such as Walter Payton, Gary Fencik (both of whom retired), Willie Gault (dealt to the Raiders), Wilber Marshall (signed as a free agent by the Redskins), and for all intents and purposes, Otis Wilson.
1987 started with the usual drama in Platteville-everyone wondering if Jim McMahon would play at all during the year, McMahon openly feuded with coach Mike Ditka, upset over the new signal-caller Jim Harbaugh that the team picked on the first round. Tension was also building due to strike talk that loomed- always a bad omen for a team.
First up for Chicago in 1987 was a matchup with the defending world champion New York Giants. As if this game wasn't tough enough in and of itself, it would be played on Monday Night Football, and the Bears would be led by 3rd-year QB Mike Tomczak. McMahon and Fuller were injured, Doug Flutie was traded, and rookie Jim Harbaugh needed to be groomed for a few years before he would be ready. The Bears pulled it out in their typical fashion, however, trouncing the world champs by a score of 34–19 behind a remarkable performance by Tomczak who completed 20 of 34 passes for 292 yards. Dennis McKinnon delighted the Soldier Field crowd that night by returning a punt 94 yards for a touchdown, it was the longest TD Punt return in the NFL in 1987. The Bears, it appeared were back. The club won their second game against the Tampa Bay Buccaneers on September 20, then the strike of 1987 was called, forcing the cancellation of all NFL games the week of September 27.
During the first days of the strike, the league pondered what to do, as most teams' players were deeply divided over whether to strike or not. This was not 1982, everyone learned, as the league decided to hire replacement players (referred to as "scabs" and "spare Bears"), among them, quarterback Sean Payton, who would later coach the New Orleans Saints to victory in Super Bowl XLIV. Cancelling half the season was not an option. Mike Ditka decided to make his feelings public about the strike, as he fully backed management on the work-stoppage. He referred to the spare players as his "real" players, a move which angered the true Bears out on strike. This turned out to be a wound not healed easily or quickly in the months to come.
The strike turned out to only last four weeks, encompassing three games, and the Bears went 2–1. The teams that hired the best replacement players did themselves a favor in the end, a group of which the Bears were a part of. When the "real" 1987 resumed, Jim McMahon was back at QB, and the Bears pulled off their biggest come-from-behind win in history, beating Tampa 27–26 after trailing 20–0. The victory proved to be inspiring, as they then won the next two games, including a 26–24 victory over the Green Bay Packers at Lambeau Field. In this game, Chicago trailed with less than a minute left, when McMahon led the team down the field for a game-winning 55-yard field goal off the leg of Kevin Butler. After the kick, Butler turned and "flipped the bird" to Packer coach Forrest Gregg, in effect saying "see you later" to the coach who was finally axed after the 1987 NFL season.
After the inspiring Green Bay win, Chicago lost a close game at Mile High Stadium to the Denver Broncos 31–29 on Monday Night Football, then beat Green Bay at home and Minnesota on the road, in the infamous "Rollerdome" game (Mike Ditka referred to the Hubert H. Humphrey Metrodome by this name, prompting the Vikings' cheerleaders to parade around on skates throughout the contest.) The Bears were 10–2 with three games left, but dropped 2 of them, and struggled into the playoffs. One of those losses was a 41–0 disaster at San Francisco at the hands of the San Francisco 49ers, and Mike Ditka threw his gum at a heckling fan, prompting assault charges to be filed against him. This was certainly not a good way to enter the playoffs.
The Bears lost 21–17 to the Washington Redskins in the divisional playoffs. They took a 14–0 lead, but the Redskins rallied behind quarterback Doug Williams to win a playoff game in Soldier Field for the second straight season. For Bears fans, they wondered where the magic of 1985 went.