My daughter was married in Disney last October. The airline told us that they may or may not have room for it as a carry on. I had a visual of lots of carry on pcs of luggage being stuffed in an overhead with a dress. My daughter flew down with her dessert party gown, I took the ball gown for the ceremony. There is no way I was letting that dress out of my sight. I bought a ticket next to me for the dress. When I walked on the plane the flight attendant said, "Uh, not sure if we will have room for that today." No, worries it had it's own seat. Funny thing is because it was so long, I was required to give the dress the window seat as I was told I had to keep the floor in front of the seats and the aisle completely clear of the dress bag.
Got from WI to Detroit, and guess what? No flight to Orlando anymore, had to fly the next day. Luckily, I was going 2 days before the wedding. I made the airline get me a hotel room with 2 queen beds so I could spread the dress out on the bed. I am so grateful that the airline screw up didn't have that dress sitting in either Orlando or Detroit overnight.
I also reserved a seat for the dress on Magical Express! Keep in mind that maybe you only need a 1 way ticket because once the wedding was done, it wouldn't be such a crisis to have the dress "misplaced" or delayed. We had friends who drove to FL take it home for us.