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Frequent Flyer Secrets: How to Fly to Hawaii for Free


I am, without a doubt, the frequent flyer expert among my family and friends. I step in when someone wants to use miles to take the trip of a lifetime. I’ve booked airline tickets using miles to Bali and Borneo to Singapore and the Seychelles to Orlando and Las Vegas. By far, however, the most frequent request I get is for assistance to use frequent flyer miles for flights to Hawaii. Here’s what I tell them…

Pick Your Island

First, decide which Hawaiian Island you wish to visit. From the continental United States, you can fly nonstop to Kahului, Maui (OGG); Kona (KOA) or Hilo (ITO) on the Big Island; Honolulu, Oahu (HNL); and Lihue, Kauai (LIH). You can also connect to other islands like Lanai and Molokai from the larger Hawaiian airports.

Which Airlines Fly to Hawaii from the United States?

Plenty of airlines offer nonstop service from the United States to Hawaii. They include Alaska Airlines, American Airlines, Delta, Hawaiian Airlines, United, and US Airways. You can also fly between the Hawaiian Islands with Hawaiian Airlines, Island Air, Go!, and Mokulele Airlines.

What Kind of Miles Are We Talking About?

The real secret to booking that free flight to Hawaii is knowing how to use your miles from Airline A to fly on Airline B. You just need to find out which alliance the carriers belong to. You can use your miles on one airline to book travel on any other airline in that alliance. The three airline alliances are OneWorld, SkyTeam, and Star Alliance.

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How to: Let’s say you’ve got British Airways Avios miles. You can use those to book an American Airlines flight, since they’re both OneWorld members. You just search for the flights on the British Airways website or call their customer service line. You don’t turn to American Airlines even though they’ll operate the flight.

Transferring Points into Miles

If you’re not airline or alliance-loyal, you can still snag free tickets by transferring credit card reward points from programs like American Express’ Membership Rewards, Chase’s Ultimate Rewards, or Starwood Preferred Guest into frequent flyer miles.

How to: So you’ve got Membership Rewards points. You could transfer them to Air Canada and then book your flight on either United or US Airways, since all three airlines are Star Alliance members. Or you could transfer them to British Airways for that American Airlines flight. Or transfer them directly to Delta or Hawaiian Airlines and make your reservation through them.

Tip: Starwood Preferred Guest program is very useful because for every 20,000 points you transfer into airline miles, SPG will give you a bonus of 5,000 miles. You can transfer SPG points into miles on all of the airlines mentioned above that fly to Hawaii. (Note: the transfer ratio is 1:1 with the exception of United, which transfers at a ratio of 2:1.)

How Many Miles Do You Need?

As a general rule, you’ll use about 40,000 miles to book one round-trip economy ticket from anywhere in the continental US to Hawaii. Business/first will run you about 75,000 miles per ticket. You’ll also pay a small amount of cash per ticket for government fees and taxes. These range from $2.50 to $85, but are generally on the lower end of the scale.

Many airlines also offer “anytime” or “flexible” awards for which you pay additional points above the lower “saver” rate. Avoid these at all costs! Instead, plan ahead, search carefully for saver/low award seats and you’ll save yourself a ton of miles.

More Important Tips & Tricks

Feeder Flights: Sometimes the hardest part about booking a free flight to Hawaii isn’t getting the long-haul nonstop segment to the islands, but the short flight from your home airport to the nonstop departure city. Consider all your alliance options to find the right repositioning flight. And look at all cabins. You may want to fly to Hawaii in first class but do you need to sit up front on the initial flight from, say, Boston to Newark?

Mix and Match: All of the above airlines—with the exception of Delta and US Airways—offer one-way award flights at half the miles. If your mileage balance isn’t large enough to book round-trip tickets with one airline, you can book one-way awards on two different carriers instead.

Be Flexible: Booking frequent flyer seats to Hawaii is one of the most popular redemptions out there. Competition for these free seats can be fierce. Be flexible with your desired travel dates. Also, think about splitting up your group in different cabins—say two in economy and two in business. If you’re booking for a large group, you may have to fly on different flights.

Break up the Reservation: If you’re a family of four looking for award seats, don’t always search for four seats at once. Airlines release reward tickets in random patterns. Four tickets may not be available right now, but two or three seats might be. Consider splitting up your reservation and booking the award seats as they become available.

Take Advantage of Your Elite Status: Log in to your frequent flyer account whenever searching for tickets online. Many airlines offer expanded inventory to their customers who have earned elite status. Also, if you’re calling to make a reservation over the phone, call the elite line instead of the general number.

Get Automated Alerts: Expert Flyer is a subscription-based service ($4.99 per month) that helps you find the award seats you’re looking for. You can set up alerts for specific flights on a number of airlines. You can even set up alerts based on your preferred cabin. Expert Flyer will email you when that award seat opens up. Then you just have to get online or call the airline before someone else snatches it up.

When All Else Fails, Call a Pro: Searching for frequent flyer reward seats can be time consuming and frustrating—especially if you haven’t done the dance before. There are several companies run by mileage gurus that will book frequent flyer tickets for you. Two of the most reputable are PointsPros and Book Your Award.

Andrea M. Rotondo is a freelance writer based in New York City. She covers cruise news and luxury travel trends for and writes for a variety of outlets, including her website Luxury Travel Mavens. Follow her on Twitter: @luxtravelmavens.

Photo credits: Airplane landing in Hawaii via

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