1. Bears - The window is closing with an aging defense, but they should still have 1-2 years to challenge for a Super Bowl victory before the D needs to be reloaded. With a formidable offense shaping up, this year looks like it's going to be their best bet.
2. Bulls - If Rose comes back healthy next year and can avoid the injury bug, the Bulls will have a shot. They could use another scoring option, but if they are all healthy, they will have a very good chance while Rip is here(and at full strength).
3. Blackhawks - Four consecutive playoff appearances and two years removed from a Stanley Cup title, they are still in good shape to be Cup contenders for years to come, so long as they get a formidable netminder and some defensive/PP help.
4. Cubs - The arrival of Theo brought a new era to Cubs baseball. It's going to be a rough couple of years before this team can realistically contend, but give them a few years and they should be able to field a team worthy of contending for a World Series(finally).
5. White Sox - A team going through an identity crisis with a farm system lacking in top prospects will have a big hill to climb in order to get back to legitimate contention. Pitching is a strength and always will be as long as pitching coach Don Cooper is on the South side, but an anemic offense will keep the Sox from being able to win the World Series for the time being.
Yes, I'm a pessimist. I know. :facepalm: