Image Credits: Kasuga Huang, Creative Commons 3.0
Published November 19, 2025 by

Cheap Flights: Portland to/from Maui-Kahului or Lihue, Hawaii $237 r/t [January-February] – Southwest / American Airlines

[11/18/2025 @ 08:29 PM CT] Deal time-stamp.
[2025-11-25 10:59:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Deals are usually valid 24 to 72 hours after posting, but can expire at any time (see time-stamp).

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Southwest and American Airlines have round-trip flights from Portland (PDX) to Maui-Kahului or Lihue, Hawaii (OGG, LIH) for $237 with a connection. Flights January to February. Departures on Monday, Tuesday, and Wednesday. Origin/Destination reversible.

American allows one carry-on bag and one personal item for free. You can avoid paying for seat selection by accepting the randomly assigned seat at the gate.

If you use the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® with AA flights, you get: a 25% inflight food and beverage discount, a $125 AA flight discount after you spend $20,000 or more in purchases during your card year, and your first checked bag is free on domestic American Airlines flights for you and up to four companions traveling on the same reservation.

Use a card like the Southwest Rapid Rewards® Plus Credit Card to earn points towards a Companion Pass®. Companion Pass is the benefit that allows you to choose one person to fly with you, free of airline charges* every time you purchase or redeem points for a flight. *Companion Pass doesn’t cover taxes and fees.

It is common to find Southwest gift-cards for sale at a discount of about -$70 to -$20 off the redeemable value at Costco and Sam’s Club. Before you finalize your booking you should check to see if you can save more money by using a gift card.

You can usually save more money by booking your flight+hotel together as a package instead of separately.

We post new flight deals often! You can check out our other deals by returning to the Front Page of our website: escape.flights (linked).

Here are some other offers that we think are worth mentioning. List updated 04/21/2026.

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Use the example date links on our website to pull up the fare.

Kahului fares: [2025-11-25 10:59:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

Kauai fares: [2025-12-21 08:28:00] This fare IS NO LONGER BEING MONITORED because the deal has expired, been removed, or became too old. If it goes back online we will send out another notification.

  • Portland, Oregon to Kauai - Extended Weekend Dates: (Expedia) Feb 26 - Mar 02 / Feb 26 - Mar 03 / Other dates: There may be more dates available than the ones we list here, use the "flexible date" button on Expedia to find similar fares.

When you are ready to book your flight or hotel, please use the links on our site to begin your booking process so we receive credit for the referral.

  • Tips: Different booking websites will often have differing routes, prices, and availability. Before you finalize your purchase, do a quick check on Expedia, Skyscanner, and Kayak to see if any other site or airline is offering a better deal.


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Ren P. Artemio

Ren P. Artemio

Ren is the Chief Director of Nap Times at Escape Houston, Escape ATX, Cheap DFW, and Escape Flights. He really likes researching airfare and the travel industry, especially when it means getting a cheap flight to anywhere (he's not picky).

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