Diving Back Into Airline Miles

Years ago, I was a miles junkie.

This was pre-kids. After reading about the pudding guy, I decided to accumulate enough miles for the hubs and I to travel to Australia via Hong Kong, in Business Class. I got most of my miles by clipping coupons off the backs of cereal boxes and by using my Citi AAdvantage credit card for almost every purchase we made.

Then we had a baby, used up our miles stash on bringing the baby home to visit the Midwest, and didn’t have time to think about miles anymore. Life lesson: Take the trip of your dreams before you get pregnant, dummy.

That all changed this year. First, when we took a family trip to Europe this summer, everyone loved it, and the kids are already asking when we’ll go on another international trip. But that trip was extravagantly expensive, not something we can repeat anytime soon, or maybe ever.

Second, a cousin started getting into the miles game, and even attended a conference to learn how to amass more miles. I was amazed to read in her recent trip report the luxurious travel conditions she’d been able to achieve through miles — mostly through sign-up bonuses on credit cards.

I was inspired. But it took more than inspiration to truly push me off the cliff into miles frenzy. It took an event: A big announcement.

Of a dear family member’s wedding. In Sydney.

We have three kids, people. It’s one thing to accumulate enough miles for two people to fly to Australia, but can I do it for five?

I think I can. And I invested hours of time yesterday afternoon when I probably should have been working to figure out various strategies for how to do it. Here are the possible flight itineraries I came up with that could get the five of us to the wedding and back with the minimum amount of further effort:

1) Fly round-trip on American from San Francisco to Sydney.

Cost: 375,000 AA miles + $511.80 taxes and fees

Advantages: Convenient and straightforward. Direct flight. Also, I already have the itinerary on hold at the moment so if I decide I can raise the necessary miles by travel time, I can just book it now.

Disadvantages: I have just under half this many miles right now, and if I fail to get them in time, I think I would have to pay $150 per ticket to cancel the reservations. This plan doesn’t take advantage of some of the non-AAdvantage points I was hoping to use.

2) Fly Hawaiian Air one-way Oakland-Sydney via Honolulu, then return via American Sydney-San Francisco

Cost: 60,000 AmEx Membership Rewards Points + 337,500 American AAdvantage miles

(I would pay for one ticket on this segment with American Express Membership Rewards Points, transferred to a Hawaiian Air mileage account, and the other four with AAdvantage miles.)

Advantages: By using Hawaiian Air one way, I’d be able to use some non-AAdvantage points I have. Oakland is very convenient for us. Plus, on such a long flight, a layover might actually be an advantage.

BIG Disadvantage: I’m not sure this part of my itinerary is actually possible. The web site MileCards asserts, “American AAdvantage no longer allows using miles on Hawaiian Airlines to and from the U.S. mainland.” I called AAdvantage customer service yesterday, and the agent told me it was possible to use AA miles to fly to Sydney on HA, but she coudln’t find an available flight for the day I asked about it, and she didn’t sound like she really knew what she was doing.

3) Fly on a combination of miles and paid tickets.

Those AmEx points I wanted to use don’t convert to AA miles. But I could still use them towards this trip if I were to purchase one of our tickets (probably one one-way segment) for cash through the American Express travel portal. I may also be getting 60,000 Chase Ultimate Rewards points soon, with which I could do the same thing.

I’m reluctant to do this because as I wrote for WiseBread recently, it’s not a great value for my points. It would also add complication to our trip if one person’s ticket was purchased separately.

How close am I to being able to pull this off? 

Right now, I have 185,199 AAdvantage milesnearly enough for 5 one-way tickets. If I book them, because our miles are spread across my account and Erik’s, I’ll actually be booking three one-way tickets with my account, then logging out and booking two one-way tickets with his. From what I understand, I’ll be able to book these tickets even if I don’t have enough miles in my account to pay for them right now, as long as I will have the required miles before the flight actually happens.

I also currently have 72,171 AmEx points to use if we go with Itinerary #2.

I’m going to bring you guys along with me on this journey to the journey. In my next post, I’ll reveal how I got the miles I have so far, and my plans for getting the miles I still need. Buckle your seatbelts!