You may bring large sums of money with you in the form of cash, money order, or traveler's checks. There is no maximum limit, however, any amount exceeding $10,000 USD must be declared upon arrival on both the Form 6059B and FinCEN 105.
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You might be surprised to learn that there is no limit on how much cash you can cross the border with. However, if you travel with more than $10,000 USD then you must declare it.
So how much cash can you fly with? You can fly with any amount of cash. No law prohibits you from bringing any amount of money on a flight. Likewise, TSA has no rules that limit how much money you can bring through security.