Not really disney related, but we are going to be embarking on an Alaska cruise soon and the list of things to pack is long. Since we'll be on a cruise and with kids I like to pack any matter of medicine we may need which fills a good sized shoebox and adds up to quite a bit of weight. Rather than packing this in my large suitcase, I'd like to put it in a small bag and check it by itself. We are flying Southwest, so paying for the checked bag is not an issue. I'm just worried about a small bag getting lost on the plane or somewhere along the way with all the huge suitcases. Has anyone checked relatively small bags? I'm traveling solo with two kids so there is a real limit to how many suitcases I can handle. This is something that would sit on the handle of my suitcase so easy enough to wheel around. Looking at checking something similar to this:
http://www.ebags.com/product/samsonite/aspire-gr8-boarding-bag/273761?productid=10302707
http://www.ebags.com/product/samsonite/aspire-gr8-boarding-bag/273761?productid=10302707