that's the thing though - I never believed that Chicago's most pressing need was QB. IMO, the formula for Chicago to be successful is to play strong D, rely on your running game, and have a QB who takes care of the ball. That's the formula used by the early Pats, Ravens, Steelers, Giants, Buccaneers, etc. to win superbowls. It's a tried and proven method for success in the NFL, especially for a team that hopes to host playoff games on the banks of Lake Michigan.
Instead, Chicago really wants to throw the ball around - they want to be as pass happy as a dome team, and I don't get it. When they went to the SB, they had roughly a 50% run/pass ratio - in 07 they were @ 43%, in 08 they were @ 45% (league average is roughly 46%). This is a team with a historically good D, a good RB and terrible WR's, yet they have not played to their strengths. I imagine Chicago wants to be a high-powered O to compete with what they see in Green Bay, and I simply don't understand why.
Had Chicago kept Orton, they could have used some of their picks to improve. consider - available @ 18, they could have had Maclin, Oher, Alex Mack, Eric Wood, Percy Harvin, Hakeem Nicks. There was definitely WR talent available. I don't know how those lineman are doing, but there are multiple game starters avaliable right there. In the 3rd round, the Bears pick was used by Pittsburgh to draft Mike Wallace. I'm not sure whom else the Bears could have been interested in at that point.
Point is, they could have built around Orton, strengthened their weaknesses, and been a decent team. Trading for cutler, IMO, reaks of a OC on the hot seat, blaming the QB for all of the shortcomings, and hoping for a miracle cure brought by a"franchise QB".
Orton, IMO, is everything that a team like Chicago needs.