I'm always curious when this type of story comes up. Is it locale based? Certain states doing funny things? Certain chain pharmacy practices? From my almost 10 years experience as a pharmacy technician in Oregon and Washington, I still have yet to see the actual cash price (not wholesale price) be cheaper than insurance.

They legally can not tell you that

Got a source for that? Absolutely not true.

If you go to Walgreens, your prescription leaflet specifically tells you how much you "saved" over the cash price. That cash price is the most expensive price you could pay for the medication. Cash price of your drug is $297? If insurance pays nothing, you'll pay $297. Ask to pay cash and you'll pay $297.

Now there are some chains that do have a list of medications that they do have cheaper (Example is Walmart's $4 Drug List, or Walgreens' paid discount program), but that's chain specific and the lists are pretty narrow in what's covered. They're loss leaders since they want to fill all your other drugs that aren't on those lists.

The other alternative is Discount Cards. Can definitely save money over insurance prices, but it's hard to know what those companies are doing with your data. You're giving a random 3rd party access to your health information. They'll give you a discount then turn around and sell your information to the highest bidder. Unfortunately sometimes a pharmacy will run your claims through one without telling you when you ask to pay cash (Some give kickbacks to the tech/pharmacist).

None of this is to say that I like the prices of drugs. Drug makers and insurance companies artificially raise prices and tell you you're getting a good deal on your "million dollar" medication.