When it’s raining on one side of an island in Hawaii, though, the sun is usually shining on another, a short drive away. However, if the priority is to avoid heavy downpours in traditionally fun-in-the-sun locations such as Waikiki, Poipu, Kona and Kihei, the worst time to go is November through April.
Cheapest days to fly in the U.S. and Canada March and April. June, July, August and September. January, February and March. May and June. July, August and September. Shop as you would year-round. Don’t shop too late, either! That said, monitor prices, and if you see a deal now, jump on it. Jan 6, 2020
When is the Cheapest Time to Visit Hawaii The Fall. September through the first two weeks of December are the off-peak or “low season” in Hawaii. April and May. The months between the end of the winter rainy season and the start of summer offer great prices and fantastic weather. Oct 4, 2019
Best Time of Year to Visit Hawaii for Low Prices Flights to Hawaii are generally at their most expensive from mid-December through mid-April. In 2019, Skyscanner estimated that flights would be cheapest in January and September and most expensive in June and December.Oct 26, 2020