Be sure you don't have any other AFCAD for another KORD in conflict. You can see what GSX is using if you open "customize airport positions" from the Add-ons->GSX menu. The name of the AFCAD in use is listed there, which might give you some clue which scenery is conflicting.
If the AFCAD in use is not the FSDT one, you won't see any jetways, because the GSX customization is tied to the AFCAD used.