In light of the events of tonight's episode, I feel that a clarification of Castiel's canon point is in order. Not that it really matters because Cas is further along than the rest of the group but ... just in case, here's what he knows and doesn't know.
Originally I said that Castiel arrived in Chicago prior to returning to Heaven, however, given what was revealed tonight, there's something else he ... can't do because it would screw up everything I've played with him, so.
Cas arrived in Chicago pre-Heaven, pre-pulling Sam from Hell, pre-all the bad life choices ever. Good intentioned life choices, but oh Cas.
That is all. You may now return to your regularly scheduled Rift-induced program.