A few months back, I sold a very expensive chip and shipped it via UPS insured for the amount that I sold the chip for. I listed the contents of the package and described the casino chip including it's face value. They asked me about it and I told them the story behind the chip and why it was worth so much. UPS didn't have a problem at all with it as long as I was willing to pay the extra amount for the insurance. Have done it for other expense chips as well.