I would not pack anything of value in my bags to be checked. TSA does go through bags.
Personally, I only wear my watch, earrings, wedding band and diamond. None of them ever come off unless I am home and I am in the process of cleaning them. I pay an extra $1000 a year for insurance on these pieces. I don't wear any costume jewelry at all... only my good stuff listed above.
We travel often and I've never had an issue. I do turn my diamond around sometimes so it is not visible, I can't conceal the gold watch and for earrings, someone would have to get them off me first.
Have fun on your vacation!