OK, I know I'm a Bulls homer so show be where I'm wrong in any of this below.
Dwight Howard to Chicago is feasible. Certainly it isn't likely and there are a myriad of factors involved. The new CBA is a major one, of course. But here is how it would have to go down:
1. Orlando continues their downward slide next season. They try to improve by trade but don't have the pieces. Speculation about Howard leaving gets worse and worse. Orlando realizes they have a Melo situation on their hands and decide to entertain trade offers.
2. There would be two criteria for a trading partner. First, it would have to be a team that Howard would want to play for. He likely wants to play for a major market and be on a team that has the talent to compete for a championship for years to come. Any team trading for Howard would want to feel comfortable that Howard would re-sign with them (assuming the new CBA still allows for this), so a trade would need to go through Howard. Next, the team needs to have some assets to trade back to Orlando. Obviously Orlando would not get full value but there has to be at least a decent return.
Chicago is, perhaps, best positioned in this scenario. Orlando would certainly get Noah and the future Bobcats' pick that Chicago owns. Expiring salaries (or cheap buyouts) of some combination of players would need to be added such as those of Korver, Brewer, Bogans and/or Watson. A player like Taj Gibson or Omer Asik (young promising players on cheap contracts) could be thrown in. It would also be possible to expand the trade to include the Bulls taking on a bad contact like Turkoglu and the Bulls adding Deng.
Howard then gets to play in a major market and play with Rose for years and years to come.
When I look around the league, I don't think I see a better trade fit. Maybe the Nets, but I don't think so. Lakers have and an aging Kobe and Gasol. Plus, does Orlando really want to take the risk on Bynum's knees? Clippers still have Donald Sterling. The Knicks don't have tradeable assets. Nor does Dallas.
Again, I'm not saying this is going to happen. It's just a possibility.