A good rule of thumb for buying plane tickets to any destination is the sooner, the better. Prices tend to increase the closer you get to your trip, as is often the case for many travel-related purchases. But we've all been guilty of playing the wait-and-watch game, hoping to get the lowest fare. This usually turns into the wait-and-watch-the-price-increase game!

We've all heard the recommendations that tickets are cheaper on a Tuesday, never purchase a plane ticket on the weekend, etc.  Well, let me tell you, I have watched and watched and watched flight fares and have rarely found any of this true.  What I have found is that prices can change day by day. They can go down but usually go up.  Save yourself the headache and stress of looking at flights daily and purchasing at the same time you're securing all of your other travel arrangements.

Regarding purchasing flights to Hawaii, I recommend the sooner, the better. Book your flight as soon as you know when you want to go and have accommodations in place.  If you want a lower fare, be flexible with the dates you can travel.  Hawaii is always a place people want to go, but if you can go during a time of fewer tourists, which is typically late April to early June and September to mid-December, you might be able to find lower flight fares.

Also, be flexible about which island to visit. I have found flights cheaper for one island than another for the same time frame. For example, at the time I wrote this, two round-trip tickets to Kauai were $800 more than two round-trip tickets to Maui for the exact same dates at the end of September—early October this year.

So, in summary, purchase as early as possible, be flexible if you can, and one thing I didn't mention, it's okay to use tools that monitor fares.  I certainly do, but I would never book through them.

To the reader who asked this question, I hope you find this helpful!