We are thinking about planning a sort of last minute trip to Oahu and the Big Island in May. We have flexible dates (we can go any time in May) and are thinking about 11-13 nights total (this would be our second trip to both islands) with 4-5 nights Oahu and 7-8 nights on the Big Island.
We want to go based on when we can find the best/ cheapest flights options. I've never booked a multi-city flight before by myself (we've used a travel agent our other trips to Hawaii), and my question is can you use the flexible dates option when booking a multi-city flight so that you can determine when the best prices would be?
So far, I've put in some different options on Kayak.
Option 1 -
I also looked into booking the flight from DC to HNL, then from KOA to DC, and then booking the one way inter-island flight (from HNL into Hilo (ITO)) separately would be about $43 per person more than Option 1, but would be easier for us than having to fly back to Oahu at the end of our trip.
I also tried putting in all 3 flights into the multi-city option on Kayak (the flight from DC to HNL, then HNL to ITO, then KOA to DC) and this came up to be way more expensive for some reason (like $114 more than Option 2). Am I doing something wrong here?
For those of you who have experience booking multi-city flights, is it better just to book the inter-island flight with Hawaiian Airlines separately from your flights to and from the mainland? Also, how do you determine when the best dates would be for the price since it doesn't seem to be letting me choose flexible dates with the multi-city itinerary.
Thanks for your help!