The Cheapest Time To Visit Hawaii: Cheap Flights & Cheap Hotels!


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Hawaii is our most requested destination at our luxury travel concierge, not least because there are some fantastic beach hotels. We have picked the best in our review of the best Four Seasons resorts in Hawaii. If you are looking for decent hotel rooms and flights at reasonable prices, our travel tip is to travel to Hawaii when it is less popular.

The good news is that Southwest Airlines will soon enter the game for this routing, so flights from the US mainland have never been cheaper to get to these magical islands.

The Most Expensive Time To Visit Hawaii

Don’t expect the best deals between mid-December through to mid-April. Everyone wants to get away for the winter, so Hawaii is super popular at this time of the year. You may be able to buy a cheap flight during these dates but don’t expect the Four Seasons Maui to shower you with deals. If you must travel in the high season, January or February tend to be cheaper than December and March.

The Cheapest Time to Visit Hawaii

The fall months, from September to mid-December, tend to be the cheapest. Expect 3 for 2 and 4 for 3 hotel deals and airfare savings of more than 10%.

The Best Weather in Hawaii

Rainfall is lowest from April to September, although it can be quite rainy right through November. I went to Hawaii in August and stayed in Waikiki, and it was hot but moist, with rain and cloud most days. Often, when the rain passed, at least some of the day was sunny, too. If you are looking to avoid the rain, I would suggest avoiding Honolulu and heading straight over to Wailea on Maui or the gorgeous Four Seasons on Lanai.

It is important to remember that the Hawaiian islands have a wet and a dry side, affecting whether you experience rain much more than the incoming weather systems. When it is raining in Honolulu, it may well be sunny in Wailea on Maui, so choose your resort location well.

The Best Times to Go Whale-watching

You will find humpback whales off the islands’ coasts from December through to May. February is thought to be the peak.

So What’s The Best Time To Go To Hawaii

The best time of year to visit Hawaii to avoid the crowds and to get those cheap flights and hotel rooms is probably May or September. Make sure you choose a sunny resort on the right side of each island, and you will be in for a treat.

That said, I love Hawaii before Christmas. Screw the prices. There is nothing like hearing Elvis warbling Christmas tunes as you dig your toes into the warm sand. For me, that’s Hawaii.

Best Airlines To Fly To Hawaii

The airline you will choose will depend largely on your departure airport. We have detailed the best airlines to fly to Hawaii in First Class. Hawaiian Airlines in First is a great choice if you don’t want to travel in Coach.

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