When to Use Cash Instead of Points
The cents-per-point test
Divide the cash price of the booking by the points it would cost. If you are getting well over 1 cent per point, redeeming is a good deal; if you are getting less than about 1 cent, pay cash and keep your points. Cardocrat values every point at a flat 1 cent precisely so you can run this test honestly.
When cash wins
Pay cash for cheap flights and hotels, where redeeming burns a lot of points for little value, and when you have no travel planned, since flexible points are more valuable kept in the bank than locked into a low-value redemption. Also pay cash if redeeming would leave you just short of a better award you actually want.
When points win
Use points for expensive cash fares, especially premium cabins and high-season hotels, where transferable points booked through the right partner can be worth several cents each. That is the upside the 1-cent floor does not capture, and it is where the game pays off. See how points work.