dated, but...
I don't fly much, the last time was in 2003, so this may be a bit dated, but here is my experience. I was returning from my father's funeral, and was bringing a few things back with me. A pair of rifles, and some other odds and ends. After having first checked with the airline, as to the proper procedure, everything went fairly smoothly with the guns, but I did have a small problem with something else.
Everything was checked (bags, gun cases) and I was waiting for the flight, when my name was called on the PA. Returning to the counter, I was given the bottle of Hoppes No.9 that had been in one suitcase. It was still in the sealed blister pack. I was informed that I could not take it, as it was a "flammable liquid". I said, "uh...ok" , took it and gave it to my brother (who was not traveling). He took it out to his car. Trip went smoothly after that.
After being cleared through gate security (and having to take off my shoes-steel toed boots) everything was fine. I was not checked again when changing planes (did not leave security area), although I did have to show my ID to get each boarding pass.
So, I would imagine, that if you can get your empty holster past the first security check without them freaking out and confiscating it, you should not have any further problems, as long as you do not leave the secure area, and then try to re-enter.
If you want to have some fun, since you are going to "fit a profile" anyway (by not having checked bags), show up a few hours early, don't check any bags, buy a one way ticket, pay cash, and WEAR the EMPTY holster! They will give you all kinds of attention!
On the other hand, if you don't enjoy body cavity searches, this might not be a good idea.