How to Fly Free

How to leverage your travel to fly free and earn First Class upgrades. Hawaii in First Class? For free? Yup.

Step one. Get a job far, far away.

Ok, this probably isn’t the choice most people would go with, but it did work for me. The bigger takeaway is that the more you travel, the more you can travel. I worked in Alaska for years, mostly wasting my miles on flights to and from work, or buying cheap flights on discount airlines. When I decided to make a concerted effort to use my miles for me, I was amazed at how easy it was to fly free. So start searching for little trips, not your dream destination, but something to sate your travel bug for a little while and help you towards your goal.

Research your mileage plans.

Not every airline has the same perks, routes, or upgrade options. I did my big push with Alaska Airlines. With Boston as a home base, this wasn’t terribly easy. Alaska only flies to three airports directly from Boston, but by researching their partners, I was able to obtain partner miles from other airlines.

MVP Status

This is more important than it looks initially. You might be tempted to use the miles that you are accumulating for a seemingly highly discounted flight before you make MVP. This is almost always a mistake. When you fly using your miles, you will not gain miles. Once you make MVP status, you will become eligible for upgrades (which is a nice perk), but even more importantly, you will earn miles faster. With Alaska, as an MVP I get 1 1/2 miles for every mile flown. As an easy example, one of my round trip flights from Boston to Alaska was roughly 8000 miles. With my MVP status, that earned me 12,000 miles. Almost enough for a free one way flight.

Get the card

If you really want to rack up miles quickly, the credit cards that airlines offer can get you there. With Alaska there were several benefits to the card (I do not advocate irresponsible credit spending, but if you can pay off your purchases immediately, you will get big dividends). The first big benefit was triple miles on all Alaska Air purchases. They also give you a pile of bonus miles for your first purchase. Don’t fall for getting an extra card though. Transferring miles between accounts will cost a good percentage, so keeping everything in one account when possible will save money.

Alaska and some other airlines also offer companion fares. So if you buy a full price flight, you can get a matching flight for $99 once a year.

So how do you fly to Hawaii First Class for free?

Obviously, the first step was to build up miles. I had a few trips on partner airlines that I was able to transfer over for a few thousand miles, and after a year of steadily flying (6 round trips BOS to ANC) to Alaska and I had 108,000 miles in my account. I was able to find us round trip tickets for 2 for 95,000 miles. But it wasn’t an even split. The trip out was 17,500/person and the trip back was 30,000/person. A little more digging and I found a First Class flight back for 40,000/person, and after transferring the needed miles from my partners account, booked this flight. With the mileage transfer and booking fees, our total bill was about $100. So While we didn’t fly 100% free, it was pretty close.

When First Class isn’t quite First Class.

How did I find a First Class trip so cheaply? (They’re usually around 80,000 miles). It wasn’t exactly First Class. Our flight had three legs, and it was apparent that we were only in First Class for one of them. MVP to the rescue, and we had reclining exit row seats for no charge (be mindful, the front exit row doesn’t recline).

But First Class is still First Class

Early boarding? Premier service at the check in counter? If any part of your ticket is First Class you get these. Also, while we could not get First Class meal service, after speaking with the gate agent, all of our other legs (including the entire outbound flight with no First Class seats) were upgraded to premium for free movie player and drink service.

Travel more. And not just for the airline miles (though you will find that the more you travel, the easier and cheaper it becomes). And if you can, fly free to somewhere that scares you. “Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.” – Mark Twain

So become a traveler, and everything else will come together.

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