It has been mentioned elsewhere in this thread, but I think the Sox missed their opportunity when they had the chance to move to Addison.
Yes, some of the old-time, die-hard Southsiders would be upset and may be lost as fans. However, the Cell is cut off from the more trendy parts of the city. Yes, the South Loop is improving, but that's several miles north. (Moving there would have been a great option)
Anyways, a great majority of the old Southsiders moved their families out to the burbs. Studies have shown a vast majority of the Sox fans live outside the city limits. So by moving to Addison, where 290 and 355 meet, just north of I-88, just south of I-90, and just west of I-294, the Sox could basically own everything from the city limits out. Easy access in and out. Public transportation would have been an issue, though.
The Angels embraced being in the OC and they let the Dodgers have LA. Now Anaheim is a major market team.