I have a feeling the asking price will be too high so he'll stay in Calgary. We just saw what Morrow went for, so it's scary to think what Iginla could get. Chiarelli is usually a pretty cautious GM and I think he'll start to look elsewhere for help at wing (like a Ryane Clowe). Lombardi did his major shakeup last year, and Chicago doesn't appear to need Iginla at all.
Pittsburgh already got Morrow, there is no need for Iginla, there is no spot on the roster for him either, unless you move one of Morrow or Dupuis down to the 3rd line, and I don't think Bylsma will do that. Pittsburgh's top 6 is set, if they make another move, it will be a depth move.
Iginla plays RW, Chicago is already set at RW with Kane and Hossa (when he gets back). What Chicago needs, is depth on LW, I think Chicago will look elsewhere to address that, or they may even stick with Saad and Stalberg on their top 2 lines, but whatever they decide to do, Iginla will likely not be a part of it.
Los Angeles: Maybe
LA might be a potential destination considering the relationship between the Sutters, but LA is very deep on forward, what they need is defense, so Iginla in LA doesn't really address a need. If LA were to make a deal with Calgary, the more likely player they may target could be Bouwmeester or Giordano.
Boston has the assets it will take to acquire Iginla, potentially making Subban, Khoklachev, Spooner, etc... available. Boston appears to be in the market for a forward, and after losing out on Morrow, they'll push for Iginla hard. With Iginla in the fold, Boston could have a top 6 consisting of power forwards in Iginla, Lucic, and Horton, sniper in Seguin, playmaker in Krejci, and two-way in Bergeron. IMO, Iginla goes to Boston, then re-signs there in the summer, because once Iginla leaves Calgary, I doubt they he'll go back, his time there will be up, the organization needs to move on.