For Chicago, this is what I'm expecting:
2 - Keith
7 - Seabrook/Chelios (and many will complain)
19 - Toews
81 - Hossa
88 - Kane
I think that an argument can, and will, be made for 4 (Hjalmarsson), 10 (Sharp), and 50 (Crawford), but the ones above I see as slam dunks that will definitely happen. These three are possible, but I'm not going to say that they will absolutely happen.
Crow has two Cups to his name, and I think a third would definitely do it. Barring that, I think that he needs at least five more great years with us to definitely get #50 retired.
Sharp was a core piece for three wins, but it all depends if the management thinks that every member of the three Cups (so far) club gets in or not.
Same for Hammer, albeit he has the benefit of still being with the club. If this core wins a fourth Cup, I think that definitely does it.
Outside of the current players (or recent) players....
28 - Larmer - think this depends on if he gets into the HOF eventually or not.