Why Hawaii Flights Are Usually Expensive
Hawaii is one of the most isolated island chains in the world. That means fewer airlines fly there, and fuel costs are higher. But that doesn't mean you have to pay $800 or more. The key is knowing when and how to book. I've found that the sweet spot is 3-5 months in advance for peak season (June-August, December) and 2-3 months for off-peak (September-November, January-May).
Best Airlines for Cheap Hawaii Flights
Southwest Airlines is my go-to. They started flying to Hawaii in 2019 and often have fares from $99 one-way from the West Coast. I've snagged Los Angeles to Honolulu for $178 round-trip. Other good options: Hawaiian Airlines (sales in January and September), Alaska Airlines (companion fare if you have their credit card), and Delta (flash sales). Avoid booking on Expedia or Kayak without checking Southwest first—they don't show up on those sites.
The Best Time to Book
I track prices using Google Flights and set alerts. For the lowest fares, book on a Tuesday or Wednesday, and fly on a Tuesday, Wednesday, or Saturday. I've saved $120 just by shifting my trip by one day. Also, avoid booking within 21 days of departure—prices skyrocket. My last trip to Maui cost $312 round-trip because I booked exactly 4 months out, on a Wednesday, for a Wednesday flight.
Use Credit Card Points to Slash the Cost
If you have Chase Ultimate Rewards or Amex Membership Rewards, you can transfer points to airlines like United, Southwest, or British Airways (for Alaska Airlines flights). I transferred 25,000 Chase points to Southwest and paid $11 in taxes for a round-trip to Kauai. That's a 3.5-cent-per-point value. Even if you don't have points, sign-up bonuses can cover a whole flight. The Chase Sapphire Preferred often has a 60,000-point bonus—enough for two round-trips.
Positioning Flights: The Secret Weapon
If you live east of the Rockies, consider a positioning flight. I once flew from New York to Los Angeles for $89 on Spirit, then LA to Honolulu for $198 on Southwest. Total: $287. Yes, it's two separate tickets, so leave at least 4 hours between flights. I've done this 3 times and never missed a connection. Just don't check bags—carry-on only.
Mistakes to Avoid
Don't book basic economy if you want a carry-on—you'll pay $50 each way. Don't fly on Fridays or Sundays. Don't ignore Oakland or San Jose if you're in the Bay Area; they're often $50 cheaper than SFO. And don't assume one airline is always cheapest. I check Southwest, Hawaiian, and Alaska every time.
My Exact Booking Strategy
1) Set a Google Flights alert 6 months out. 2) When prices drop below $400, book immediately—they rarely go lower. 3) Use points if you have them. 4) Fly midweek. 5) Pack light. Follow this, and you'll be sipping mai tais in Waikiki for less than your monthly car payment.