The $99 Hawaii flight is back, and yes, it is real if you are willing to work around the calendar airlines have attached to it. Both Alaska Airlines and United Airlines are ready to deal.
Alaska is selling $99 one-way Saver fares from San Diego to Kahului, Maui. United is matching with $99 basic economy from San Francisco to Lihue on Kauai, and Alaska is also showing $99 from Los Angeles to Kona on the Big Island on select April and May dates. That headline alone is enough to trigger the usual reflex to check dates before someone else grabs the seat.
We have covered enough of these sales to know that the number and the actual reality are rarely the same. The fare exists, but it lives on specific midweek dates, and inside basic economy rules that come with real tradeoffs many travelers only notice after they click through.
Where the $99 seats actually show up.
On Alaska, the San Diego to Kahului route in Saver fare shows the following as of mid-February.
March: 12, 17
April: 7, 8, 9, 14, 15, 16, 21, 28
May: 5, 6, 13
United’s San Francisco to Lihue $99 basic economy follows a similar midweek rhythm.
April: 12, 13, 14, 19, 20, 26, 27, 28, 29
May: 10
Alaska’s Los Angeles to Kona route is also showing $99 on select April and May midweek dates.
April: 7, 8, 14, 15, 16, 21, 22, 23, 28, 29
May: 5, 13
Across all three routes, the cheapest pricing is concentrated in the middle of the week. Fridays and Sundays climb quickly. If you need a traditional long weekend, the $99 headline fades fast.
Families will notice something else immediately. San Diego Unified spring break runs from March 28 through April 5. LAUSD spring break runs March 27 through April 5. SFUSD is March 27 through April 3. There are no $99 dates on these routes during those school breaks. The families most likely to chase a $99 Hawaii ticket simply cannot use these dates without pulling kids out of school.
If you are wondering about Honolulu, we did check. We are not seeing consistent $99 pricing to HNL on these California routes right now. The sharpest deals are to Maui, Kauai, and the Big Island.
The jump to regular economy is where the math changes.
On Alaska’s San Diego to Kahului route, the cheapest regular economy seat currently shows at $145, with most April and May dates clustering between $154 and $165. That makes the gap between $99 Saver and regular economy about $46 to $66 one way.
On United’s San Francisco to Lihue route, the cheapest regular economy is $149 on the same April and May dates where $99 basic is available. That creates a clean $50 one way difference.
On Alaska’s Los Angeles to Kona route, regular economy pricing is generally landing in the mid $140s to mid $160s on those same dates, again putting the spread at roughly $45 to $65 one way.
For a couple flying roundtrip, the difference between $99 basic and roughly $149 regular works out to about $200 total on United and slightly less on Alaska, depending on the exact date. On a Hawaii trip that will likely cost thousands once lodging, rental car, and everything else are factored in, that difference starts to look like a flexibility decision rather than a massive savings event.
What $99 basic actually means.
On Alaska, Saver includes a carry-on and a personal item, but you cannot choose your seat at booking, and your assignment is made at check in, often resulting in a middle seat toward the back of the plane.
Changes and cancellations are not allowed after the 24-hour grace period. If you cancel at least 14 days before departure, you receive only 50% of the ticket value as travel credit. Boarding is in the last group, which increases the odds that overhead bin space is already tight by the time you reach your row. Saver earns only 30% of normal mileage and elite qualifying credit, and there is no same day standby regardless of status.
On United basic economy, the sharpest difference is the carry-on rule. On many United basic tickets, a full size carry-on is not included unless you hold elite status or a co-branded credit card. That means if you plan to use the overhead bin, you may be paying roughly $35 each way on top of the $99 fare. Add that to both directions for two people, and your rock bottom fare can quietly swell by well over $100. Advance seat selection is restricted unless you pay extra, changes are limited, and boarding is last. Mileage earning is reduced compared with standard economy.
Regular economy on all three routes restores seat selection, fuller mileage credit, and change flexibility. On a five hour plus flight to Hawaii, being able to choose your seat is not a minor perk. Many readers have told us they would gladly pay an extra $50 to avoid a middle seat for that long, while others are happy to gamble if the savings are real.
Deal or trap depends on who you are.
The $99 headline is real, but it is narrow and rule heavy. It works best for solo travelers, couples with flexible schedules, retirees, and remote workers who can leave midweek without disruption. It does not work well for families tied to school calendars or travelers who need weekend departures.
When you step back and run the numbers across San Diego to Maui, San Francisco to Kauai, and Los Angeles to the Big Island, the choice is consistent. You can lock in $99 and accept a middle seat, last boarding group, reduced mileage credit, and almost no flexibility, or you can spend about $50 more one way and buy back a seat choice and change freedom on a long flight over the Pacific.
So when you see $99 to Hawaii from California, are you booking immediately and living with the restrictions, or are you paying the extra and calling it money well spent?
Flight availability at time of publishing. Airline inventory changes up to 5 times daily, so check. Book directly online at your airline of choice. These are not an advertised sale.
Lead Photo: © Beat of Hawaii on Oahu.
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