I won't ask how you got your hands on Valium without a scrip, but the answer is no, not on a domestic flight. Just put it in a pillbox and you won't be bothered.
Controlled substance + no prescription = trouble if you're caught. I wouldn't chance it. Go to the doctor and get a prescription. How hard could that be?
When I fly, I carry my prescriptions in a small case divided for each day in my briefcase. Printouts of all prescriptions are also in that briefcase -- just in case. (It's easier than carrying the prescription bottles, especially when I only need a few days, not the entire month's worth!)
Very. Most physicians (other than psychiatrists) will prescribe no more than a 15-day supply, because it is addictive. It is one of those drugs that tends to raise a red flag with a doctor if you ask for it, and you are more likely to be prescribed something else entirely, such as an SSRI.
I do have a scrip for it (though I get generic diazepam, not the brand-name version with the little v-cutout). When travelling domestically, I carry it in a divided pillbox along with my other meds. I fly at least 50x per year, and I've never been asked about it. The only time TSA will ever ask about oral meds is if you are carrying an unusually large quantity; looking for drugs is not really their job.
Customs agents are a different matter entirely: international flights require the dispensing packaging.
Very. Most physicians (other than psychiatrists) will prescribe no more than a 15-day supply, because it is addictive. It is one of those drugs that tends to raise a red flag with a doctor if you ask for it, and you are more likely to be prescribed something else entirely, such as an SSRI.
As it should be with a controlled substance. My point was "How hard can it be to go to your doctor?" not How hard is it to get a prescription for an addictive controlled drug.
To the OP, you could ask for a sleep aid, like Sonata or Ambien, both of which may be easier to get and both will help you sleep.
Bring your prescription if you have one. But in any case, I've never heard, read or seen anybody be questioned by TSA for carrying a small number of pills. That's not what they are looking for.
Now if you brought on board hundreds of pills or 2-pound bag of oregano, you might get a few questions.