We were too cheap to check any bags on our flights to and from Florida, so we just carried everything on. Since we bought 4 tickets we didn't think we'd have any problem getting all our stuff on. The one thing we didn't really factor in was that the boys wouldn't really be able to carry anything and would instead need to be carried. Here's Ed's creative solution:
He seriously schlepped Joel through both the Orlando and O'Hare airports like this. It was quite the spectacle. I even saw someone take a picture with their camera phone.