At pretty much every opportunity, he talks about wanting to leave Italian football. Just the other day he said explicitly, "I am not happy in Italian football." So where will he land?
You sorta have to assume that he won't stay in Italy, and won't go to Germany. So that leaves England and Spain. Assume he will only go to one of the biggest soccer clubs in the world, which I think is fair, as he's shown he has an ego.
In Spain, that leaves Real Madrid and Barcelona. Yes, there are some other clubs, but they are dwarfed by the big 2. Barcelona's job will be held by Pep Guardiola until he doesn't want it. But they are super committed to attacking, and Mourinho is a little more tactical. Madrid's job could be open, as they crashed out of the Champions League already. If they don't win
In England, Chelsea, Manchester United, Man City, Liverpool, Arsenal are probably the clubs Mourinho would deem as worthy of him. Man U won't be open until Sir Alex Ferguson decides to retire, and put me in the camp that doesn't seem him retiring soon. Arsenal won't kick Wenger out, as they play the 2nd most stylish football in the world. Chelsea seems unlikely since Abramovich fired him a few years ago, although Mourinho said nice things after he brilliantly defeated them a few weeks ago in the Champions League. I think Chelsea is a very outside chance.
So I think it comes down to Liverpool, Man City, and Real Madrid. I think that if Madrid manages to win La Liga, Pellegrini will be retained. I can't guarantee it, but I think so. Liverpool and Man City are fighting for the 4th spot in the English Premier League, though Tottenham could take it as well, as they have some very quality players -- Wilson Palacios, Defoe, Peter Crouch.
Rafael Beniten is under pressure at Liverpool. Somehow, and perhaps I am crazy, I still think Liverpool is not crazy enough to fire him. Liverpool may be the biggest club in the world historically, so I think they aren't too happy right now. Even so, they've been unlucky with injuries, Benitez has been a little limited in the transfer budget, so I think Liverpool will hold on to him. Of course, if Liverpool does fire him, I think Madrid might furtively interview Benitez even if Real wins La Liga.
As for Man City, after buying Carloz Tevez, Gareth Barry, Emmanuel Adebayor, etc, if they don't get into the Champions League, one has to think that they might fire Roberto Mancini.
To be completely honest, I think there's a very good chance we see Jose Mourinho at Real Madrid, Liverpool or Manchester City within the next 2 years.