McCarthy is the only one of the under 30 somethings that the Cubs might get. I think the word to sum the Cubs offseason strategy is going to be value. If enough teams are scared off by the injury history that the Cubs can make a reasonable offer to land McCarthy then he will be a Cub. Otherwise I think the swing guys that want a chance to start, BleacherNation has been pushing Carlos Villanueva as an option, would seem to be the best chance at bringing in starters for value. In that scenario guys in their early 30s that are willing to take one or two year deals would certainly be an option (think DeJesus type).
Headley isn't an option because Padres are rightfully going to ask the moon for one of the few 3B that is both a plus defender and bat. Add on the fact that you have two more years of cost control, and the price would include at least one of the big three prospects to just get the conversation started.
Castillo is going to be the starting catcher. There might be a battle for the backup catcher spot between Clevenger, Recker and maybe some other veteran they bring on a minor league deal, but I don't see any major dollars being committed to this spot.
OF and 3B are the offensive spots that the Cubs will try to bring some help. They will need an OF especially if they manage to find the right deal for Sori. It isn't going to be Hamilton, and it probably isn't going to be the second level guys like Upton. 3B is going to be tough, and bringing Stewart back I don't think is out of the question. Though there have been whispers that the FO hasn't been happy with his effort rehabbing and his dedication to the sport, e.g. his somewhat infamous late night twitter activity. Youkilis I could see being an option if a market doesn't develop for him, but it would seem like the White Sox would be a better fit if he wanted to stay in CHicago.