Hawaiian Airlines Boston and Portland Sale

Cheapest Cities for Hawaii Flights and Costs

Updated 2/15/2020. Recent updates regarding which mainland departure locations are the cheapest cities for Hawaii flights due to increased competition. Travelers using these airports can expect to benefit most in terms of consistently lowest prices and greatest availability. Check the starting prices below to see how little you can expect to spend for winter, spring and fall travel.

Hawaii Flights and Cheapest Departure Cities

Los Angeles. Prices are trending down (15-25%) intermittently on multiple airlines due to new and anticipated competition. Target prices start at $300’s round trip, even to Kauai. And perhaps it will get even better than that. That as Hawaiian Airlines introduces more flights on their fleet of new aircraft and Southwest Hawaii gets going with more new routes. When Southwest adds Los Angeles to Hawaii flights, prices will be even lower.

New York. Intermittent sales on Hawaiian Airlines (nonstop), and Alaska Airlines, among others. Target prices for 2019/2020 start in the $500’s.

Oakland. Good Hawaii deals overall on Hawaiian Airlines, Alaska Airlines, and Southwest Airlines. This is Southwest Hawaii’s base. Target prices for 2019/2020 start at $300 but we might see even more $200 RT fares ahead. Oakland will be one of the cities to benefit most from Southwest Hawaii flights, as those expand.

Portland. We’ve had less frequent sales on Hawaiian AirlinesAlaska AirlinesDelta Airlines, and especially United Airlines. Target prices during on-again, off-again sales from $300, or even less. That having been said, significant competition is lacking out of Portland at present.

Sacramento. Expect frequent but short-lasting sales with target prices beginning in $300’s, with the occasional $200 RT. Remainder of 2019/2020 should see lower fares based on new flights coming from Southwest.

San Diego. Better deals overall than Los Angeles via Hawaiian AirlinesAlaska Airlines, and soon Southwest Airlines. 2019/2020 target prices start at $300 or less. Perhaps a few $200 RT offers will appear. We should continue to see lower fares, due to competition and the upcoming announcement of Southwest flights from San Diego and perhaps Los Angeles.

San Francisco. Reasonable prices on Hawaiian Airlines, and others. Target prices for 2019/2020 starting in low $300’s.

San Jose. Still one of if not the best “Hawaii deals” gateway cities. Check Hawaiian Airlines, Alaska Airlines, and Southwest Airlines. Target prices start at low $300’s and this may improve still. Watch for some as low as $200 RT. This is another Southwest gateway city to Hawaii.

Seattle. Less frequent sales on multiple carriers including Hawaiian Airlines, Delta Airlines, and United Airlines. Sale prices have started in $300’s. Seattle lacks significant, fare-reducing competition at this time.

Note: We frequently update this post on Cheapest Cities for Hawaii Flights. Look for more information to come soon.

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Visit Cheapest Time to Fly to Hawaii for more info and to ask questions.

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