Hi Jen.....I can't tell you exactly how early you can do the bag check/airline check-in. I have always had a morning flight. But you shouldn't have any problem checking in with the airline people at the resort when you are checking out of the resort. I believe their desk opens at 5 a.m. Just a side note...your bags are not transported via DME...it is a service basically provided by those 'pariticipating' airlines. You deal directly with TSA (or whatever they're called) right at the resort. The bags may go back to the airport via the DME truck but I can't say for sure. And yes, once you have checked your luggage at your resort, you can just go directly to the security lines...no need to stop at the airline counter. I just love being able to do that!!!