booking travel
Award Booking Disney Family Travel Miles and Points US Destinations

How I decided between the multitude of travel options to Orlando

For some reason, domestic travel stresses me out more than international travel. Booking the travel, that is. The reasons for this are pretty simple – international travel presents way fewer options. If I’m trying to book a premium cabin with miles (which I try to do), then my options really boil down to how persistently I check award space

Domestic travel between cities like Boston and Orlando, however, can be booked any number of ways:

  • Cash
  • Cash Equivalents (ThankYou Points, Ultimate Rewards, Membership Rewards, Flexperks)
  • Airline miles (fixed value)
  • Airline miles (region based)
  • Airline miles (distance based)
  • Gift cards

As I like to do from time to time, I’m going to break down my thought process and how I decided to book my flights. Surprise surprise, I screwed up! Oh well…


I have reached the point in my life where traveling with kids, I now refuse to 

a) fly with a connection (at least for destinations within 2-3 hours)


b) leave super early or super late

That meant that there were only four options: Delta, Jetblue, Spirit, or Southwest. Since I try to spend cash last (TM Free-quent Flyer), I dismissed Spirit immediately. This also helped me avoid any carry on bag fee calculations.

For various reasons, I also only needed to buy a one-way flight. That meant that Flexperks were probably out, since the cheapest award you can get is for a flight up to $400. The cash prices weren’t going to approach that.

Checking cash prices

Due to my parameters, I quickly cut down my options. Since UA and AA both don’t have direct flights, I eliminated distance based mileage options (British Airways or ANA). I’m not sitting on any gift cards to any of those airlines, so I eliminated that option as well.

booking travel
Hmm a few days out – these flights must not be too full since the prices haven’t gone up too much

I knew that the majority of my remaining options were going to be a function of the cash price for flights. Cash, cash equivalents, and fixed value points are all tied to the going rate for the flight you want. 

So I threw my city pair and dates into my favorite flight search engines (Kayak and Google Flights) and found that the cheapest non-stop flight was around $175 (Delta). Jetblue was going at around $200 and I think Southwest was pricing out at like $240 (I threw this out after looking at the cost in both cash and points so I forget).

Converting cash prices to cash equivalents

Once I had the cash prices in hand, I set about looking at how much those flights would cost if I paid with cash equivalents. I’ve learned to not worry about how much I earned the miles for in general and instead just focus on how much value I’m getting at the time.

So the cost of these flights with cash equivalents was pretty easy to calculate:

Membership Rewards (Business Platinum): 17,500 cents / 1 cents per point = 17,500 MR points

ThankYou Points (Citi Prestige): 17,500 cents / 1.3 cents per point = 13,461 TYP

Ultimate Rewards Points (Chase Sapphire Reserve): 17,500 cents / 1.5 cents per point = 11,667 UR points

The Jetblue flight cost about 15-16,000 points, I can’t remember exactly. Anyway, at this point Ultimate Rewards were looking pretty good but I still had to check region based mileage programs.

Delta Air Lines, Boston’s hidden gem

I shall not continue beating the dead horse. But suffice it to say, Delta’s website showed three award seats available for 10,000 points each. This looked like a better deal to me than all of my other options, so I booked the tickets. I made sure to pay the taxes and fees with my Delta Gold card so that I’d get a free checked bag (a mistake I’ve made in the past). 

booking travel
Looks like I got in at the right time on Delta though!

10,000 points for $175 tickets felt like a great deal – especially since Delta miles feel less valuable than UR points, my next cheapest option. Getting a value of over 1.5 cents per point felt like a real win. Except.

My foolish mistake

At this point, savvy readers probably already know what I messed up. Robert Dwyer, ever the voice of reason, pointed this out to me after I had already booked. Since I have the AMEX Business Platinum AND Delta is my airline of choice, I could have gotten 50% back off a pay with points redemption.

Short version: I could have paid 17,500 points for the flight, but get 8,750 points back for a total cost of 8,750 MR points AND mileage earning. Dooooooooooooh.

Final Thoughts

I’m still shaking my head at myself for missing that. The great things about miles and points are you have a ton of options to save money, but having lots of options means you sometimes miss the obvious one. Hopefully, running through my thought process will help some of you avoid that mistake and help inspire you to think through all your options as you plan travel. And hey, even though I could have saved a few miles, I got a travel related post out of this and fulfilled the bossman’s wishes!


Just an average joe trying to fly his family for less

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