i am planning on accepting the offer..but last year i applied as well, was wait-listed, and eventually received an offer (turned down for a fellowship elsewhere)
the program is ultra-competitive, so getting wait-listed is still pretty awesome..i think that you should email your potential supervisors and let them know how interested you are in the program, etc...for a top school they are surprisingly friendly, so you should not hesitate to express your desire to be picked off the wait-list..what field are you looking to specialize in?
also, if chicago is really the place you want to be, you should look into the MAPSS program (im assuming you got accepted into this in the wait-list letter that you received)..its a pretty wonderful program in and of itself, and could be a stepping stone into the phd program if the wait-list thing does not work out..
they have a recruitment weekend for this as well, and I would advise you going to this (if indeed you have been accepted into this program..if not, disregard last 3 sentences!)
i hope that it works out for you!