UPDATE: Nonstop flights from Oakland and San Jose to both Honolulu and Maui dropped to $318 roundtrip and inter-island flights dropped to $39 one-way for daily fall travel.
Today, Southwest Airlines extended its booking schedule through the holiday season and you can now book tickets on Southwest for travel through January 5, 2020. While there aren't any new Hawaii route announcements, you can now book Southwest flights to Hawaii in November and December starting from $358 roundtrip.
These prices aren't anywhere near the amazing $98 roundtrip flights that were for sale this spring when Southwest first started selling tickets to Hawaii, but you may want to book these quickly if you want to travel on Southwest to Hawaii this fall. Ever since those super cheap spring fares sold out, Southwest fares to Hawaii have been extraordinarily high.
Travel on Mondays, Tuesdays, Wednesdays, and Thursdays, in November and December.
Peak holiday travel around Thanksgiving and Christmas will be priced much higher and some of these fares have limited availability.
On a few routes, you can find these prices for travel over New Year's if you're originating in Hawaii and trying to return from the mainland back to Hawaii on January 1 or 2, 2020.
These fares are unadvertised and may jump in price at any time.
Please note, these fares are only available on Southwest.com. Other carriers regularly match these sale fares, so be sure to compare to find the best deal.
All fares also work in the reverse direction.
These fares include a carry-on bag, a personal item, and two free checked bags up to 50lbs/23kg each.
Southwest has an open seating policy, which means there are no assigned seats and you'll get to choose your seat during boarding. The order of boarding is determined by the time of check-in so check-in exactly 24 hours before departure or pay for priority boarding for a better choice of seat.
You may find similar or lower fares in these markets on other carriers, but all other airlines charge for checked bags—some even charge for carry-on bags. Southwest has the advantage of two free checked bags and no change fees.
If you want to fly into one island and back from another, you can purchase one-way flights for about half the roundtrip price and combine with $39 inter-island Southwest flights.
And if you're looking for flights from further east, you'll have to wait until Southwest begins flying overnight (red-eye) flights. Until then, it is not possible to make an onward connection flying from Hawaii to points east on Southwest. You may be able to book a one-way flight from the Midwest or East Coast to Hawaii on one itinerary, but the return flight would require two separate tickets and an overnight stop on the West Coast.
Searching Southwest's website, I found a flight departing Oakland OAK on Monday, November 18, with a return flight from Honolulu HNL on Monday, November 25, for $318 roundtrip.