Geri told us she has an April cruise booked, and getting her family from San Francisco to Honolulu is costing more than the cruise itself. When she asked the cruise line to arrange flights, the quote came back at $1,500 per person round trip, about twice the outrageous price she’d already found on her own. She asked us two questions, including one we’ve answered thousands of times over the years: when is the best time to buy airfare to Hawaii?
Our answer has changed dramatically. For nearly two decades, we helped readers anticipate Hawaii fare sales and decide whether to buy or wait. Today we’re taking a different approach, and our own upcoming West Coast trip provides a particularly good example. We paid $600 per person for first class from Kauai to Oakland, and since we purchased, the same flight now costs considerably more.
When we could actually predict Hawaii airfare sales.
In January 2016, a reader planning an August trip from Oakland to Maui asked whether fares might come down. Our answer was remarkably specific: “Too early. Spring to early summer should yield sales.” We could make those predictions because we watched the airlines compete, often anticipating the next promotion based on what we’d seen occur repeatedly.
Our original Cheapest Time to Fly to Hawaii guide became one of BOH’s most popular articles ever, with millions of reads, 4,651 comments, and more than 61,000 Facebook likes. Readers asked about specific dates, departure cities, and whether the fares they saw would improve. We spent years answering them individually, often recommending when to hold off and when to grab a ticket immediately. We became known for finding the answer.
Even in October 2022, our Hawaii airfare booking advice distinguished between peak travel periods, when we recommended buying as far out as 330 days, and other times when buying within the final 90 days could work well. Those recommendations reflected the very different pricing patterns we were still seeing across seasons.
That approach became increasingly unreliable. The regular sales that once arrived from Hawaiian, Alaska, Southwest, and United have largely disappeared, replaced by occasional discounts on selected routes and dates. We documented the disappearance of Hawaii airfare sales this summer, after years of watching them become harder to find. Hawaii still has less expensive travel seasons, but that no longer means there’s a dependable window to buy tickets.
Why we chose Oakland and paid $600 for first class.
Back in June, we wrote about a Kauai-to-San Francisco airfare search that left us staring at economy fares of $669 to $701 one way. First class was approaching $2,000 for that holiday-period trip, and we weren’t willing to pay anything close to that.
For our upcoming West Coast trip, San Francisco International was our preferred arrival airport. But when we found a nonstop Alaska/Hawaiian first-class flight from Lihue to Oakland for $600 per person, we booked it. Oakland wasn’t our first choice, but getting into San Francisco from there is perfectly manageable and just as good for our purposes. Why spend hundreds more just to land at SFO?
Today’s Google Flights prices make that decision look even better. On November 10, our exact Oakland nonstop is listed at $875 per person in first class. Alaska’s nonstop to SFO is $1,115, while United shows $1,168 for a late-night redeye departure and an extraordinary $2,783 for its afternoon nonstop. All of those are one-way first-class prices.
We paid $1,200 for two. The same Oakland flight would now cost $1,750, while Alaska’s currently listed SFO option would be $2,230. We have no regrets about choosing Oakland, and we haven’t stopped watching SFO. We have alerts set, and if anything pops up before departure, we’ll be on it. Until then, we already have a flight we’re perfectly happy with.
Our two tickets have different ways out.
Refundability is a major part of how we book Hawaii flights today. We prefer to pay a bit more for a fully refundable fare, which lets us secure the flight we want while we keep looking for something better. If a lower fare comes along, we can cancel and get our money back instead of being locked into an airline credit, which we dread.
That wasn’t an option on the Alaska outbound when we booked, at least not one we could find. We went ahead anyway because we fly between the Hawaiian islands frequently enough that, if we needed to cancel, we could put the eligible Alaska ticket credit toward future interisland travel. We knew we’d have a practical use for the money, even though it wouldn’t come back to the original credit card payment method.
Our return is on United, also in first class, but we bought that ticket fully refundable. Since making the purchase and setting up our Google Flights alerts, we’ve watched the price climb approximately 250%. We’re still holding our original fare, while hoping to improve it. If we find something better, we can change without being stuck with a less useful United credit.
We also didn’t insist on booking a round trip with one airline. Using Alaska outbound and United returning let us choose the best combination of price, schedule, and flexibility separately for each direction. Sometimes the two directions call for entirely different decisions.
We buy the ticket, but the shopping game never stops.
We’ve used Google Flights price alerts for years, including long after buying tickets. In 2023, Jeff received an alert when a Hawaiian Airlines first-class fare from Lihue to Los Angeles suddenly dropped from $1,659 to $630. He bought immediately, and the price went back up shortly afterward. We described that experience in How We Saved 62% On Hawaiian Airlines First Class.
The alerts remain one of our most valuable tools, but how we use them has evolved. Rather than waiting for a hoped-for sale before committing to a trip, we now secure a fare we’re prepared to pay and continue monitoring. We’re watching both Oakland and San Francisco for the outbound and return, even though we already have our tickets. If the right fare appears, fine. If it doesn’t, we lose nothing.
We’re always outplaying the airlines. Jeff considers it part of his job, and after decades of following Hawaii airfares personally, and over the past 20 years for Beat of Hawaii, we’re still finding ways to come out ahead. Sometimes that means finding an unusually low price, sometimes choosing a different airport, and sometimes paying a little more for the freedom simply to change our minds.
What we’d tell Geri about her April cruise.
Geri’s cruise dates are presumably fixed, which makes waiting for some imagined airfare sweet spot especially risky. We’d start by comparing flights from San Francisco, Oakland, and San Jose, looking at schedules and the actual cost for everyone traveling. We’d also build in enough time before the cruise departure to avoid having a flight delay or cancellation jeopardize the entire vacation.
We’d book directly with the airline as soon as we found an acceptable fare, preferably refundable, and if not, then with an airline where we are likely to use the credit before it expires, and then keep the price alerts active afterward. For a family, the cost of a fare change can be substantial, so it’s worth knowing whether a cancellation returns cash or provides a credit before purchasing.
As for Geri’s suspicion that the cruise line is receiving kickbacks, we have no evidence of that. Do airlines sell wholesale tickets to cruise companies? Very likely. But cruise-line air arrangements can involve different fares and conditions, and the $1,500 quote alone doesn’t tell us why it was so much higher than what she found independently. We’d compare exactly what was included before considering it.
We’d be interested to hear from other readers who have already purchased Hawaii flights and kept tracking prices afterward. Did you eventually find a better fare, or have you watched the price climb while being relieved you booked when you did?
By Rob and Jeff, Beat of Hawaii.
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