Southwest Hawaii Comeback Targets Peak-Season Price Shock

Southwest has broken a years-long silence on Hawaii growth with its first new flights to the islands since the pandemic-era expansion. In this first but likely not last Hawaii move, starting March 5, 2026, the airline will bring back daily nonstop service between San Diego and Maui. That’s a route it cut long ago and had shown no signs of coming back. But the more interesting part is the timing, right as the Alaska–Hawaiian tie-up plays out, giving Southwest an unusual opening to challenge its two biggest rivals in one of their most important markets.

The return comes as some spring break fares on Hawaiian/Alaska push $700 round-trip, and this is taking place at Alaska Airlines’ biggest Southern California stronghold. With the Alaska–Hawaiian merger still in motion, Southwest may see this as a golden opportunity to secure more Hawaii market share while the competition is preoccupied with other matters.

Timeline of Southwest’s San Diego–Maui service.

San Diego–Maui was once a regular in Southwest’s Hawaii schedule. Then, as the airline pulled back from the islands, the route was dropped entirely, while focus shifted to other California and Vegas gateways, and eventually to overnight red-eyes.

For BOH reader Mark in Encinitas, that exit meant taking Maui off the list altogether, as fares on other airlines climbed fast. Linda in Carlsbad told us she might revisit Maui again if prices come down, and she hasn’t forgotten about Southwest.

Southwest first launched daily nonstop flights from San Diego to Maui in June 2021, followed by the addition of a second daily flight soon thereafter. By late 2023, the airline had quietly dropped the route from its schedule. Starting in 2024 and into 2025, there was no San Diego–Maui service at all. Now, in March 2026, the carrier plans to bring back daily, year-round service between San Diego and Maui as part of its latest schedule expansion.

Why Southwest picked 2026 for a return.

Southwest’s March schedule extension adds new service not only from San Diego to Maui, but also from San Diego to Portland, Eugene, Seattle, and Puerto Vallarta. Each of these goes head-to-head with Alaska Airlines, which has increased its San Diego presence by nearly ten percent year over year.

With the Alaska–Hawaiian merger fast concluding, Southwest may be making a calculated move to maintain and grow its presence in Hawaii before a combined competitor becomes even stronger. The integration process leaves a window where schedules, pricing, and priorities are in flux, a window Southwest appears ready to attempt to use to its advantage.

The airline recently told Beat of Hawaii it remains committed to the islands, and this move puts that promise into action starting with more seats headed to Maui.

Will Southwest’s return lower Maui fares.

Southwest was previously known for launching Hawaii routes with eye-catching fares well below the going rate. No specials have been announced yet, but history suggests that competitors tend to match, at least for a while, when Southwest enters the market. Whether that’s still true in today’s new airline environment remains to be seen.

But if that does play out here, this could be the break Maui-bound travelers have been waiting for, especially with spring break prices already brushing the stratosphere.

What’s next for Southwest in Hawaii.

This return to Maui drops right into the middle of the Alaska–Hawaiian tie-up, and that timing is, of course, no accident. While those two work on combining schedules, fleets, and operations, Southwest sees an opportunity to grab market share and remind Hawaii travelers that it’s still in the game.

If this works, expect Southwest to consider pressing its advantage while the Alaska/Hawaiian competition remains distracted. Additional Hawaii service from Southern California, Las Vegas, or Phoenix could follow.

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