Visit Hawaii round-trip on Southwest from $278 or 17,934 points

Jan 16, 2020

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Southwest Airlines flights to Hawaii are on sale. Say no more.

As part of the airline’s current promotion, there are discounted fares to Hawaii from the continental United States. Flights are cheapest from the West Coast — between Oakland and Honolulu, or San Jose and Maui, fares are as low as $139 one-way or $278 round-trip.

We’ve found a good number of discounted flights from January to May, which is perfect for a last-minute escape from winter, a Valentine’s Day getaway (Southwest is known as the LUV carrier) or a spring treat for yourself before the kids get out of school.

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As always, Southwest doesn’t charge any fees for up to two checked bags per passenger. You can even substitute a surfboard for free as one of your pieces of checked baggage.

Southwest doesn’t serve meals on board, so bring a snack or lunch or be prepared to nibble on a complimentary snack box.

Not sure what to expect? Read our full review of the Southwest Hawaii flight experience

And of course, if you’re traveling over the Pacific for a Hawaiian vacation, you should visit more than one island. Flights between the Hawaiian islands begin at just $39 one-way. At these prices, you might as well visit them all, right?

To book, enter your origin city on and select your destination. These are the mainland cities from which Southwest flies nonstop to Hawaii:

Airline: Southwest
Cost: From $139 one-way from the continental U.S., or $39 one-way between Hawaiian Islands
Dates: January-May 2020
Pay with: Platinum Card® from American Express (5x on airfare booked directly with the airline); Citi Prestige® Card (5x on airfare); Citi Premier® CardChase Sapphire Reserve (3x on airfare); American Express® Gold Card (3x on airfare when booked directly with the airline), or Chase Sapphire Preferred Card (2x on travel)

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Here are some examples of specific flights that are available:

Oakland (OAK) to Honolulu (HNL) round-trip in May on 17,934 Rapid Rewards points and $11:

or Oakland (OAK) to Honolulu (HNL) round-trip on the same dates in May for $278:

San Jose (SJC) to Maui (OGG) round-trip in February for $278:

or San Jose (SJC) to Maui (OGG) round-trip in February for $17,934 Rapid Rewards points and $11:

Maximize your purchase

Don’t forget to use a credit card that earns additional points on airfare purchases, such as the Platinum Card® from American Express (5x on flights booked directly with airlines or American Express Travel), Chase Sapphire ReserveAmerican Express® Gold Card Citi Premier® CardCiti Prestige Card (5x on airfare), or the Chase Sapphire Preferred Card (2x on all travel purchases). Check out this guide for more on maximizing airfare purchases.

Featured image by Getty Images.

Delta SkyMiles® Platinum American Express Card

Earn 90,000 bonus miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new card in the first three months of card membership. Offer ends 11/10/2021.

With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.

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More Things to Know
  • Limited Time Offer: Earn 90,000 Bonus Miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new Card in your first 3 months. Offer expires 11/10/2021.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
  • Earn 1X Miles on all other eligible purchases.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. *Payment of the government imposed taxes and fees of no more than $75 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights.
  • Fee Credit for Global Entry or TSA Pre✓®.
  • Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
  • No Foreign Transaction Fees.
  • $250 Annual Fee.
  • Terms Apply.
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