The yearly Alaska Airlines Companion Fare that comes with the Bank of America Alaska Airlines Visa Signature Credit Card is awesome. However, the question becomes, WHICH trip is the best trip to use it on? I’ve had the credit card and gotten the companion fare deal for many years now. But this year was the first year that I had three potential uses for it. A good problem to have. Maybe you’ve had this good problem as well :)

It did, however, require a thorough look at comparing prices and hotels. If I’m paying cash for a hotel stay, I always use Pruvo to monitor for price drops, so that figures into my choice too. I also looked at what other miles/points I had available for these routes to finally make my choice. It was a lesson in perseverance! Here’s what I did. I was originating from San Diego and my trips were to Hawaii, New York City, and Boston. My dates for Hawaii and Boston were somewhat flexible, but my New York City dates were not.

Great Circle Mapper: http://www.gcmap.com/mapui?P=hnl-san,san-bos,san-jfk

The first task was to get basic fares on these routes. As I show you the numbers, remember it’s for two people. I did change the dates up some on the Boston and Hawaii fares to see if I could make the prices go down. New York City came in between $679 and $707 and Hawaii was around $853. Boston was hovering around $600. So between Boston and Hawaii, that’s quite a difference. But could I get hotels for these same dates using points or points and cash? And each trip had different amounts of hotel nights I would need, though as it turned out, only by one night.

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My preferred hotel chains are Hyatt and Starwood, though I also have a stash of Hilton points. I knew New York City would be the most expensive and challenging to find availability, and I didn’t have a choice as to which nights, so I started with Hawaii and Boston first, thinking those two trips needed to be booked first and then I’d circle back around to New York City.

I did a bunch of hotel availability searching, switching around dates, and saw what I could book both in Boston and Hawaii. It looked like Boston was making the most sense based on the companion fare and also being able to get a hotel on cash/points. But then how would I go to Hawaii?

My next step was to see if I could use British Airways Avios to book my Hawaii trip on Alaska Airlines. BINGO! That was the key that unlocked all three trips. British Airways Avios were not available to Boston, but they were to Hawaii. That was the trip I booked first because I could use either points for a hotel in Hawaii or use my Citi Prestige Credit Card for the fourth night free benefit.

Then I went back and booked the Boston trip using the Bank of America Alaska Airlines Companion Fare. The fare came to $605 for 2 passengers, which for a round-trip non-stop to Boston I consider to be a great fare. I used Hyatt points and cash for my stay at the Boston Hyatt Regency (stay tuned for my hotel review).

Ah New York City. I ended up using British Airways Avios for Alaska Airlines on the outbound and for the return, I flew American Airlines, cashing in some AA gift cards that I had accumulated. After checking hotels with Hotel Hustle, and looking at potential Airbnb units and prices, I ended up staying with cousins. Wonderful benefit, for sure!

That’s my adventure booking flights using the Bank of America Alaska Airlines Companion Fare. Could I have improved on this process? Do you have an obvious trip winner for your companion fare each year or does it ever get this complicated? Please let me know in the comments!