By Alison Fox
August 31, 2019
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Bundled up in puffy overcoats, hats, gloves, and multiple layers, it’s easy to dream about a sun-filled vacation to the warm beaches of Hawaii. But the thing is, you can’t wait until you’re downright frigid to book that trip.

In fact, you can save up to five times off the cost of your trip if you start planning four to five months in advance — so, like now — Liana Corwin, a consumer travel expert at Hopper, told Travel + Leisure.

“[For] people who want to travel during the holidays and in the winter months, we find that the further in advance they start tracking their trips, the better chance they have of getting a deal,” Corwin said. “One kind of good rule of thumb is you obviously don’t want to purchase a trip too close to the actual time you want to get away… For a leisure destination like Hawaii, you’re going to want to book further in advance, at least a month out.”

For hotels, travelers should look to book about three months in advance of going, she added.

“You’re getting a better deal if you're looking even earlier,” Corwin said. “Now would be a great time to start looking and booking, frankly, if you're looking to travel in the winter.”

October is the absolute cheapest time to fly to Hawaii with an average round trip flight price of $511 for economy seats, according to Hopper’s data, followed by November, which has an average price of $604 for a roundtrip flight. If you want to soak up the expansive nature and pristine beaches of the Hawaiian islands in January (when temperatures hover in the 80s), you’re looking at an average round trip flight of $617.

It should come as no surprise that the cheapest airports to fly to Hawaii from are on the West Coast. In January, you’ll find flights as low as $425 from Ontario, Cali., which is just east of L.A., and flights as low as $438 from Portland, Ore.

The cheapest flight from the East Coast, according to Hopper’s data, is from New York’s JFK Airport, where you can fly to Hawaii for as low as $634 in January.

Once you’re in Hawaii, you can then fly from island to island (Southwest Airlines recently started offering flights between several islands with fares as low as $49 each way) to take in the clear blue water of Oahu and the beautiful coves on Maui from some of the best beaches in Hawaii.

If you are a procrastinator, however, there is hope for you yet: You may get a pretty good deal by waiting until the absolute last minute to book a flight to Hawaii during December to February, Laura Molnar, the senior brand manager at Travelocity, told Travel + Leisure in an email.

In fact, the gamble could save you $100 or more on a flight and more than $50 per night on a hotel if you wait to book about one week before you travel.

“Overall, travelers can find ways to save this winter,” Molnar said. “It just depends on their schedule and flexibility.”

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