I would call the airline and ask them what kind of assistance you could expect, what they'll do to help you, etc. I just flew by myself with my 18 mo and 35 weeks PG which was a bit of an ordeal, but I did find it manageable. I got my 18 mo her own seat, the hardest part was getting her car seat through the airport and through security while having to worry about her at the same time. I would think a lot depends on #1 as well. Will he stay with you in the airport, will he sleep on the plane, things like that make a big difference as to how easy your trip will be. Personally, I think with the right amount of planning, it is manageable and doable, just takes a lot of thought and planning.