Going straight from the playing field to a professional head coaching job is unheard of in the NFL these days. The path for prospective coaches in the NFL is usually, entry level quality control coach - assistant to an assistant - positional coach - coordinator - head coach, or something along those lines.
Running an NFL team is much more than the Xs and Os. It's having great time management, acting as a psychologist, being comfortable with delegation, media relations, and various other intangibles. Working your way up through the ranks is the best way to learn many of these aspects.
Just because a player is known for his intense study habits and his impeccable knowledge of the Xs and Os, that doesn't always translate to a success as a head coach. Mike Singletary is a prime example of a guy universally expected to be a solid NFL head coach, but his stint in San Francisco didn't end well.
Recently retired Brian Urlacher was as cerebral a player as you would find, and his football I.Q. would make him an obvious candidate to go into coaching.
Speaking of cerebral linebackers, Lance Briggs is another knowledgeable player that may have the chops to coach.
Roberto Garza is a player that seems to have the stoic disposition of a football coach.
Back up QB Josh McCown has bounced around the league, picking up valuable contacts along the way, and he has some coaching experience.
Are there any current or recently retired Bears you can see becoming a Head Coach some day?