Lei over: How East Coast travelers can get free First Class tickets to Hawaii on their trip to California
A transcontinental route combined with a free round-trip ticket to Hawaii — how pineapple sweet can that be! In fact, it’s quintessential FCF thinking — i.e. something most people never consider when flying but which yields a Business or First Class ticket for way less, or at the very least, a more valuable product for the same money. This is how it works.
Transcon Daylight Robbery
We published our latest lament on ridiculously high transcon fares — recently in the $2,000+ plus price range for nonstops between Los Angeles or San Francisco and New York on American, Delta, and United (that aren't 6 a.m. departures or red eyes). We cover that in detail here. Just when we got accustomed to those $2,000 round-trips (after being accustomed to $1,000 round-trips), one month later the average transcon fare jumped to $2,300+. I get grumpy when five or six months ago fares were a third to half of what they are now, as you can see here and here. That's where the Hula Loophole comes in.
What the Heck Is the Hula Loophole?
The strategy involves combining Hawaiian and transcon routes to save money — and add a Hawaiian vacation at the same time. Adding a bit of Hawaii to anything is a good thing, right? Here’s how to catch this palm tree swaying.

Example OF Hawaii For Free: Boston > Kauai > LOS Angeles > Boston
In this example, you can jump on the Hula Loophole for little more than a transcon fare. In the screenshot below, Boston to Los Angeles in Business/First Class typically goes for $2,553. But if you fly from Boston, stop in Los Angeles and then on to places like Kauai, Maui, Honolulu, and Kona before returning back to Boston, then your fare would actually be less at $2,397 (screenshot below).
Sample Trips to Cali that Get First Class to Hawaii for Free
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Play with your pricing starting on the East Coast and stopping in places like Kauai, Maui, Honolulu, and Kona before continuing on to California on your way back to the East Coast.
That’s a hulapalooza of a deal.