Kauai, Hawaii
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As winter takes full grip across the USA, the notion of a getaway to a balmy, beautiful place with crystal water, lush forest and good vibes is more attractive than ever. For under $260 round trip to Kona or Maui, you might as well. American, Alaska and Hawaiian have fantastic deals right now, so here’s how to get some sunshine on the cheap…

hawaiian airlinesThe Hawaii Deals

Cyber Monday, Travel Tuesday and all that may technically be over, but there are big offers lurking. You can fly round trip to Hawaii from San Francisco, Los Angeles, San Diego. Portland, Seattle and Las Vegas are all under $300 round trip a well. If you’re holding out hope for something further East, Dallas and Chicago are also both available around $425 round trip.

These deals are all basic economy, which means they don’t include a checked bag, but when you’re going to a place where bathing suits are considered formal wear, it’s fairly easy to fit everything into a full sized carry on. Don’t forget to use your small personal item allowance too…

The Dates You Can Travel

There’s lots of opportunity to cash in on these great deals in 2020 with wide open availability from January through May, with the very lowest prices in January and February. There’s also flights under $300 round trip in September and October, in case you’re trying to plan ahead.

To find the best prices easily, you’ll want to depart the USA between Monday and Thursday, and a Sunday night stay seems to be the only requirement. Basically, you could leave Thursday or come back Monday, or leave Monday and come back the next Monday. Longer is fine too…

a hotel with a pool and palm trees
Andaz Maui, a Hyatt hotel.

How To Book These Airfare Steals

We’ve made easy to use links so that you can go directly to the best prices from each city, find the low prices and then change dates to work for you. Simple enough, right? Here are the best deals from each city to Maui, and if you just swap the destination to Kona or Honolulu, you should see similar pricing, like…

Don’t forget to use a credit card that maximizes your airfare purchase with up to 5x points per dollar spent. And in case you’re trying to figure out how you can possibly squeeze everything into a carry on, here are some killer packing tips.

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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