Stewardess Please Prepare for Take-Off

With all the traveling the McGlone family is about to embark on, I am starting to panic as to the logistics of how this will work.
We are taking a flight to Hartford, Connecticut on Thanksgiving. Then 2 weeks later flying out to Ireland for Christmas, New Years, and my Birthday. I love to travel but with a 10 month old baby YIKES!!
To my grandmothers, there are no other grandchildren... which means we have to come with car seat, pack-n-play and stroller. OMGsh. Same with Ireland, because Kevin's brother is having a baby the week before we get there (scheduled c-section) and so they are going to be using their smallest car seat. And we NEED the stroller in the airport.
We bought a cover last night that you put the car seat in and it locks and protects it from all the nasty'ness on a plane. We have switched to a "big boy" car seat because Elliott weighs 22.4 lbs and the weight limit on his ultra cute safari one is 22 lbs. It always shows red in the little holes where you look to make sure its adjusted properly in the car, and it never is. So we have to take the "big boy" car seat with us, which means it does not attach to our stroller lol. sigh

We are planning on putting our pack-n-play in a duffel bag and checking it as baggage as well, which if it works for Connecticut then we can do the same for Ireland. I guess this is going to be a trial run for us... so much to pack and get.
UGH and the formula to declare when going through security... man people in line are going to HATE me.

I have been told to feed Elliott while taking off and landing but if anyone else has ever traveled with babies/toddlers I'd greatly appreciate the advice. I'm starting now to gather everything we are going to need because I tend to be anal about organization.



On another note.... I had mentioned that Elliott got another tooth a few days ago... well today he cut another on the top left!!! So when I said he can sprout them like no tomorrow... I really ment it!! So he's got 6.5 teeth (lol one that started to cut through in October, bottom left, has seem to stop but you can still see it. Even tho the one that just came in is out further. So we wont make it an official 7 just yet).