In 1991 the Bears had the #22 overall pick. They drafted Stan Thomas, OT, Texas. He started seven games in his career. Eleven picks later, the Atlanta Falcons drafted Brett Favre.
In 2005 the Bears had the #4 overall pick. They drafted Cedric Benson, RB, Texas. He lasted three season there before being released. Twenty picks later, the Packers drafted Aaron Rodgers.
In 2020 the Bears had the #19 overall pick, but they traded it to the Raiders for Khalil Mack. Seven picks later, the Packers drafted Jordan Love.
Meanwhile, during that time the Bears drafted Will Furrer, Cade McNown, Rex Grossman, Kyle Orton, Mitch Trubisky, and Justin Fields in the top four rounds.
The Bears had a chance to draft all three of them.