Lisa & I are going to Hawaii this winter – on a Mileage Run? = Priceless!

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Lisa at the Polynesian Cultural Village - Hawaii 1971

My wife lived in Hawaii for a few years in the 1970’s. While I loved Swedish summers she loves to tell about being able to get out of school early on Wednesdays just cuz it was Wednesday and they did what else – went to the beach. That does sound nice.

Fast forward to 2014. What really sounds nice is getting away from the SNOW in the Midwest for a few days this winter. I love Grand Cayman, but it has been a long time since I was back in Hawaii and there are a ton of things I want to see. And we are going back!

So how did this work out. A few weeks back Mommy Points gave me a heads up (thank you!)tiny arrow over a great price to Hawaii from IAH and I text alerted it outtiny arrow as well. Now you know me, it will be 2014, and I will need MQMs then too to re-qualify for Diamond for 2015. And even when I get that done, I sure don’t want to end 2014 with zero rollover MQMs so having more in the bank is always nice. But bring my wife on a Mileage Run? And just about on our anniversary? Have I lost my mind? Well…

First know I don’t “drag” my wife on mileage runs. She is Gold Medallion, a gift from my Diamond Status, but on many of the routes I pick she would not upgrade and that would mean she would be in the big seat and I would be back in coach. Plus, we don’t need two Diamonds in the family. But she said she would like to join me on one some time if we ended up someplace nice. That someplace nice became Hawaii in winter! Now I did make a few concessions that cost me a few miles as we are NOT doing a redeye as my wife only likes to fly night flights when she has a flat seat!

Now you know the most important part of this, not the cost, but the above. But let’s look at the cost. The key thing when it comes to any of these deals is to just book. Have two weeks that can work? Book both then call your +1. Why? As this one did, they go away fast. You have 24hrs to cancel with Delta and if you wait they could be gone! Also, I got the standard comments about cost to position as well as emails to that effect. Here is where I can not stress this enough when it comes to a mileage run – where it starts does not matter. Why? That is why you have things like the Barclay’s Arrival World Mastercardtiny arrow it is such a good choice.  I mean, racking up a ton of Delta Elite qualifying miles cost some dollars as I will break down next. But being able to position to the start city for “free” and earn more miles and get 10% points back = Priceless!

Other good choices to consider are the US Bank FlexPerks personal cardtiny arrow and/or business cardtiny arrow (both can go to one account and no problem sending Lisa’s FlexPerks points to metiny arrow btw)!

Air. For this trip, I just paid out of pocket for the two tickets. For $862, for the two of us total, this is a great deal when you look at what I am getting. I will give up a few MQMs to fly daytime flights only to make Lisa happy. But look at the math. I will pick up just under 10,000 MQMs and between the two of us a total of 40,000 Skymiles. Now at a minimum the Skymiles are worth $400 but I value them higher at 2-3 cents each as I will redeem my Delta points for trips to Sweden in business class so to me this Hawaii part of the trip is at worst break-even after earning points back.

Hotels. I have SPG, Hilton, IHG. I will not be paying for the hotel rooms for my IAH overnights or the time on the island. I have top tier or mid tier with all of them. There will be upgrades and there will be perks. This part should cost me nothing.

Car. I have a bunch of Hertz points and may or may not use them here. I may just work the price with codes and get a convertible and just eat that cost. Thinking on this one still.

What will cost me a bit is another trip with Blue Hawaiian Helicopters but without question another “Priceless” World Mastercard moment in time you will never forget! We so enjoyed the ride on Maui over Haleakala the last time we went to Hawaii and how many times in your life do you get to ride around the islands this way!

Anyway, the hard part is done. I have the tickets there and will now look forward to schedule changes to tweak the tickets for more goodies and routes 😉 – Rene


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  1. Looking forward to my first Chicago Seminars. I would be happy to buy you a beer Friday afternoon depending upon your arrival time ..I will be there after 2pm

  2. Blue Hawaiian!! We did the trip on the big island. The flight over the volcano’s were outstanding!! The views of the rest of the island were what you would dream about if you were a bird. Try and get the front seats. BTW I have my Blue Hawaiian shirt on today here in Chicago. See you Friday.

  3. I jumped on a similar deal from ewr-hnl.
    I know you cannot use medallion upgrades on flights to Hawaii, but can you use miles to upgrade?

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