The Monsters of the Midway is most widely known as the nickname for the National Football League's Chicago Bears—particularly the dominant teams of 1940 and 1941. The name was revived when the 1985 Chicago Bears proved to be similarly dominant, and has been used as a nickname for the Bears. The name got another renaissance in 2006 when the Bears returned to the Super Bowl thanks to their dominant defense and again in the 2018 season, when the dominant Chicago defense led the team to an NFC North championship.
The nickname Monsters of the Midway was originally applied to the University of Chicago "Maroons", a college football team under the leadership of Amos Alonzo Stagg. "Midway" is a reference to the Midway Plaisance, a long, green swath of boulevard space bordering the southern end of the campus between 59th and 60th Streets and running from Washington Park to Jackson Park on Chicago's South Side. The U of C ended its major college football program in 1939, around a time of several Bears NFL Championships. During this time, their home field was Wrigley Field, the legendary home of the Chicago Cubs, on the North Side of the city, roughly 12 miles (20 km) from the Midway. The "C" symbol on their helmets is borrowed from the U of C Maroons. The moniker is also used by the university's Velo Club bicycle racing team, for their annual criterium in May on the Midway.
It is not, contrary to some mentions, a reference to Chicago's Midway Airport, which was known as "Chicago Municipal Airport" until 1949, at which time it was renamed to honor veterans of the Battle of Midway.
The popularity of "Monsters of the Midway" was renewed by the dominant Chicago Bears defense of 1985. That year the Bears went 15–1 in the regular season. In the playoffs the Bears posted two shutouts against the New York Giants (21–0) and the Los Angeles Rams (24–0). This culminated in the Super Bowl, wherein they defeated the New England Patriots 46–10.
The 1985 Bears defense was ranked first in the NFL in points allowed and yards allowed. That year defensive end Richard Dent led the league in sacks and linebacker Mike Singletary was named the AP NFL Defensive Player of the Year. Both players were two of five Bears from that team enshrined into the Pro Football Hall of Fame, the others being running back Walter Payton, defensive end Dan Hampton, and coach Mike Ditka.
In 2018, the Chicago Bears partnered with Israel Idonije to publish a webcomic strip titled, Monsters of the Midway. The comic strip featured current and former Bears players, who fought monsters, cryptids, and villains modeled after other NFL teams. The series was revived for the 2019 season.
TSR published a game entitled Monsters of the Midway  in a 1982 edition of their magazine Dragon. It was a football simulation with various fantasy characters taking the place of football players.
The game Mutant League Football referenced the name, calling one of its fictional teams the "Midway Monsters".