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In On Points, Brian Kelly, founder of The Points Guy, shares his strategies for getting the most out of your points and miles.

Brian Kelly
March 15, 2016

It’s not too early to think about using your frequent flyer miles to get to Cuba.

In the last 14 months, President Obama has relaxed restrictions on U.S. citizens traveling to Cuba, which made it easier—though far from hassle-free—to plan a trip to the island nation. I know from experience, having visited twice since then. The first time, I had to book through a Canadian company and buy my visa en route in Grand Cayman. The second time, I had to fill out a travel application that stated I would be visiting for “journalistic activity,”  and arrive at the airport five hours before my charter flight to Santa Maria.

But soon there will be scheduled commercial flights from the U.S. to Cuba—as early as September, in fact. Airlines were asked to submit their proposed routes the other week. Nine companies are vying for a chance to fly, including Southwest, JetBlue, and the three major carriers.

Once flights are for sale, they should also be available for redemption using frequent flyer miles. Here’s what you’re likely to see from the airlines.  

American Airlines

American, which has a hub in Miami, stands to operate the most flights to Cuba. The carrier is proposing to fly to five cities besides Havana, and is likely to get many of them since Havana is limited to just 20 daily flights from the U.S., out of a total of 110 a day to the country.

American is changing its rates for award tickets on March 22; though you’ll generally need to redeem more miles for flights, not all of the changes are negative. Havana is about 330 miles from Miami, so getting there could be a real mileage deal.  Flights to the Caribbean in general will also be cheaper: economy seats will cost 15,000 miles versus the current 17,500 and business-class tickets will be 25,000 miles  instead of 27,500.

Delta Air Lines

Delta will likely operate flights to Havana from their largest hub, which is in Atlanta. On Delta you can redeem 15,000 SkyMiles each way for economy or 30,000 SkyMiles each way for first class, though peak periods cost more.

United Airlines

United recently announced flights from Newark/New York, Houston, Washington D.C., and Chicago to Havana. Awards to Cuba will cost 17,500 miles each way for economy or 30,000 miles for business/first class.

Southwest Airlines

Southwest has applied to operate nonstop service to Cuba from Fort Lauderdale, Tampa, and Orlando. Awards on Southwest are based on the type of fare you purchase, but for Wanna Get Away flights you can generally get 1.9 cents per point in value, so a $500 Wanna Get Away fare to Cuba would cost about 26,300 Rapid Rewards points.

Jet Blue

Scott Resnick, JetBlue’s director of loyalty marketing, told me, “We envision TrueBlue
flight redemptions will be allowed for travel on JetBlue commercial flights between the U.S and Cuba subject to any restrictions in place.” It looks like these flights will take off from New York JFK, Fort Lauderdale, and Tampa.  

Similar to Southwest, JetBlue awards are based on the type of fare you buy, but for Blue fare economy you can generally get 1.6 cents per point in value. A $500 Blue fare to Cuba would cost about 31,250 TrueBlue points.

There are still many factors to take into account before a “best” program can be determined, like the cost of fares, since JetBlue and Southwest peg their awards to the ticket price. If seats are cheap due to the new supply on the market, then JetBlue and Southwest (and American from Miami) will be clear winners. If fares are comparable to what they are now ($600 or more in economy and $1,000-plus in first class), then United and Delta may make more sense because their programs are based on zones.

No matter what, travel between the U.S. and Cuba will be easier than ever before. If you’ve never considered Cuba as an option, you might want to—especially if you’ve got a stash of frequent flyer miles burning a hole in your pocket.

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