Would this work?
 

Let's say I deposit money to an online gambling site with a credit card. If it's registered as a purchase, that would mean I'd get miles from it. Then I withdraw the money without betting (or bet just enough to also get a bonus from the casino) and repeat the process.

They will more than likely issue you a credit card refund. As with any purchase, once the funds are credited back to your account, the miles are credited back also.

This concept was tried with cruise ship casinos and worked for awhile some time back. Think the key is offshore transactions? Might work in physical casinos offshore? Virtual casinos, not so.

The problem is withdrawing your money, most have fees or will issue you a gift card. I haven't found a way to get my money back with out paying something or getting the funds in a way that can be deposited to pay the cc bill. If you find one pm me

http://vegasclick.com/online/legal.html says:

It's against federal law for banks to handle online gambling transactions (e.g., players making deposits or withdrawals into or from an online casino). Again, it's against the law for the banks to handle the transactions, not for you to try the transactions.

Could you not just deposit with a CC but cash out to a different account?

More to the point, do any of the major CC's allow you to deposit using thier credit cards? I seem to remember reading somewhere it is in their T+C's not to be used for gambling - particularly AMEX?

Thanks

Most credit cards won't work, they deny the charges b/c it is online gambling. Debit cards do work though...which leads me to ask, what about using GC's? The risk here is with all the gambling sites being shut down randomly and sued by the US government...do you want to risk a large amount being sent there and then tied up? On top of that, i'm pretty sure once you make a few deposits and don't gamble, they will catch on.