Using points or miles vs. paying cash

I’m on vacation.

You: Well I’m not.

Are you upset?

You: Not at you.  Just wish I had more vacation time.

What would you do with it?

You: Go somewhere.

Where?

You: Don’t know.

Would you use points, miles, or pay cash?

You: Never sure what the right thing to do is. Hey, how do you evaluate it?

Personally, I try to make sure that I get maximum (or at least not minimum) value from my points.

You: So what did you do for this trip?

I paid for the airfare and used points for the hotel.

You: Why?

I was all set to use points for the airfare.  The cost was to be 35,000 miles per ticket.  Then I checked the cost to pay cash and saw that by moving the trip up by a day, the price was about $250 per ticket.  In my mind, getting less than one cent per mile was poor value for all those late nights flying around the country earning the miles.  So I passed on the free ticket.

Still, I admit that I occasionally wonder if this airline will one day just completely disappear and take my miles with them. But so far, I haven’t lost any sleep. Or any miles.

You: What about the hotel?

The hotel was a different story. First, I have so many hotel points that I just don’t value each one quite as highly as I do the miles.  Second, there are always great deals with hotel points for their higher tier (those who travel frequently) customers.  So I get more bang from my hotel points in comparison to my perceived cost of acquisition (sleeping at night seems so much easier than connecting at O’Hare) so I use my hotel points more liberally.

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Agree with my approach?  Not so much?  How do you decide when to pay for something vs. when to use points? Do you do math or simply take the free whenever it is available?

Tags: free flights, free hotel stays, using miles, using points