In 1989, the Chicago Bears signed Waddle as an undrafted free agent. During his first two years with the Bears, he struggled to make an impact as a receiver. Waddle lacked the size and speed to distinguish himself from other Bears wide receivers and remained on the lower rungs of the team's depth chart. He received a chance to start in 1991 after the Bears lost starters due to injuries. In a nationally televised Monday night game against the Jets, he made eight catches for 102 yards in an overtime win. In Chicago's wild card playoff loss to Dallas (17-13), Waddle was the Bears' sole standout performer on the offensive side of the ball, catching nine passes for 104 yards and a touchdown. His performance established him as a mainstay in the Bears lineup and clinched him a spot on the famed All-Madden Team.