Idk about you, but for me the worst part about a trip is having to book the flight. For me, it’s probably the most stressful because it’s so expensive and flights can always change due to conditions beyond my control… it’s also possible I’ve been screwed and stranded a time or two so I’m still bitter. But, using your miles to book flights makes the process so much easier and cheaper… or so I thought…

Since our wedding date and venue set, I was comfortable booking our honeymoon for shortly after. Naturally, being the planner that I am, I started booking flights in November, the year before.

I did this for a number of reasons:

1. Flights are cheaper and more available, points wise, the further out you book.
2. Most of the hotels on the Greek Islands are small hotels so they book up fast.

As I was looking at flights I saw that I could use 30k American Airline (“AA”) miles each way (so 120k total) or I could pay around $1,700 per person ($3,400 total). 30k for a flight to Europe was an incredibly good deal and I wanted to jump on it! Unfortunately, I only had 100k AA miles so I was 20k short. I knew I could pay for one person’s flight with points and spend 60k points and $1,700 for the other person’s flight. But then I thought “how much can it really cost to purchase 20k points?”

Normally, my rule of thumb is to NEVER, under any circumstance, purchase airline points. Hotel points are a different story (I actually talk about it in a previous blog post, here) but airline points typically are too risky.

I never thought I’d say this but in this instance I made an exception and broke my rule, ONLY because I knew that I could get a flight at an amazing rate. However, this decision did cost me more than I expected. But, was it worth it…. I think.

Here was my cost breakdown:

Purchasing 20k points on AA.com would cost $560 (still cheaper than the $1,700 I would have had to spend on one plane ticket)

Taxes and fees for purchasing the points $75 (…. well ‘screw you too’ but $620 is still cheaper than $1,700)

Taxes and fees after using points to pay for the flights with points, $1,560!!!!! This one was a little harder to swallow because I always forget how much taxes and fees are when you travel broad ( I had a similar reaction when I paid over $300 in fees for Jamaica) But, I would have had to pay these fees anyway, even if I were using real dollars, which is how I rationalized it. Technically, I didn’t spend any more money than I would have spent not using my points.

Overall, my flights would have cost around $5,000 ( $1,700*2 for flights + $1,150 for taxes and fees) and I only spent $2,180… I still spent way more than I intended, but I saved a little less than $3,000!!!

Now, I’m not changing my ways and saying that purchasing miles is now worth it, but make sure you do the math before ruling it out.