Well if you're going to Bali, I guess it's number 2 lol. It has more the spirit of adventure and the taste of foreign paradises! I think it fits you well and makes you look quite sexy. If I were the boy sitting next to you in the plane, it would have its effects... Plus, the jean short goes way better with your bag than does the first outfit.
A long dress could prove inconvenient while drying to board the plane, especially if the engine is already started; trust me on this one, my grandpa had to chase a flying ticket that was caught in a draft by the turbine... Never seen an old man run so fast!!! :D
Planes and airports are typically pretty cold in my experience and fashion has never been a priority for me on a travel day. I do like the second outfit more, but honestly, you'd be better off just wearing something more comfortable. Whenever I travel, I just wear sneakers, leggings, tank top, and a sweater so I can comfortably take up multiple seats by laying across them and waiting for my flight. Also, something stretchy enough so I could sit in awkward positions on a plane lol.
1st is too dressy for flying. The second is the better option but if it's a long ride you should go more with something thats cozy and cute. After a few hours in a plane the shorts are going to start giving you unwanted cameltoe and your shirt will get rumpled. If you have the day a head of you when you get to your destination, I would wear something comfy on the plane and change in the bathroom when I get off.