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As reported by Thrifty Traveler Premium, there is a nice fare battle going that has brought down fares on United from New York to Hawaii, to as low as $389 round trip. Dates start in late August and continue into November. Sale prices are on for each of the islands, so search your preferred airports. Also keep in mind that these flights should be bookable via the Chase Travel Portal for as few as ~26K Ultimate Rewards round trip with the Sapphire Reserve.
- Airfares on both United and American from $389 round trip between New York and the Hawaiian Islands (Honolulu / HNL, Lihue / LIH, Maui / OGG, Kona / KOA)
- Availability from late August through November
Where to book
- Google Flights (easiest to search dates)
- Chase Travel Portal (available from ~26K Ultimate Rewards round trip with the CSR)
These are some excellent prices for round trip travel from New York, especially for the late summer dates. Cheap fares are available to each island. For example, here’s New York to Maui for $389 round trip from September 6th-13th:
That same itinterary is available through the Chase Travel Portal. If you have the Chase Sapphire Reserve and can therefore use your points at 1.5c each towards paid airfare, you could book that itinerary for about 26,000 Ultimate Rewards round trip.
If you want to start your journey earlier in August and stay for a bit, you can catch a one-way out on American for less than $200 in mid-August and pair it with a ~$200 return on United in September.
Plenty of other routes are possible. See the booking links above. It’s easiest to start with Google Flights as you can search multiple airports at once (See: How to find great business class fares with Google Flights as the tips in that post also apply to economy class sales like this). Keep in mind that in most cases you should have 24 hours to cancel if you change your mind, so there is little risk in booking if you see something that you think might fit your plans. Note that it is also possible to open jaw (i.e. fly into one island and home from another) should you wish to see more than one island (and you should!).