I had this exact same question a few months ago. I was pretty sure I wanted the umbrella for the easy folding and didn't worry about the airport damaging it since it's less expensive. I even did tons of research and bought a nicer one that had a few bells and whistles (one hand collapse, bigger wheels, good undercarriage storage, reclines flat etc.. I tried it out this summer at the zoo, on a few walks, the mall, etc. Results - I would HATE it in Disney. My stride is completely different in the umbrella and I don't want that frustration in the miles you walk at Disney. It doesn't have a tray for my 22 month old's snacks and drinks, and the canopy coverage isn't great for a small child since he sits lower.