I shipped 2 bottles ground as I did not want the bottles to go into an unpressurized belly of a plane. The problem is they send your package by plane anyway sometimes so wrap it up tight! I do not tell them that I am shipping beer as there is no need as long as YOU know it will get into the right hands and not their teenage kids...
Best to just not mention what it is. My buddy told them once what he was shipping and they would not take it.
As far as shipping via airplane, there is no issue. I've brought beer back as checked luggage from trips before, and nearly always ship my beer via 2 day. Being in a plane won't hurt it.
It is their policy to not allow the shipping of alcohol of any type unless there is a contract agreement with ups and its legal in your state. I've been flat denied shipping here in ny because it said "homebrew competition" in the address. It does depend on the store/driver too. Some don't care or ask. Some have grilled me on the contents of my package. I don't want to deal with the hassle so I tell them its sauce. Which is sorta not lying. ;-)