CheapAir Says it's First U.S. Online Agent Offering Flights to Havana, Cuba

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A screenshot of CheapAir's new Havana booking option.


Travel to Cuba for Americans has become steadily easier since late 2014, and it appears another barrier to entry has been lifted.

CheapAir.com announced Thursday that it has become the first online travel agent in the U.S. to offer flights to Cuba in a single transaction. But there are still some caveats, and whether this catches on with travelers remains to be seen.

For its part, CheapAir says the demand has been there since January, when a key law for travel to Cuba was changed: while Americans still need to claim one of 12 authorized reasons for entry, such as education or religious activities, they no longer need to obtain a license for it.

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The online company promises to make visiting Havana much easier. (Photo: Thinkstock)

“Since the rule change, we have seen a surge in search volumes for travel to Cuba,” said CheapAir CEO Jeff Klee in a release. “Arranging flights to Cuba is a little complicated, but it’s the kind of thing we’re good at and our technology platform is flexible enough to make it possible. Our team did a great job building it out in just a few weeks’ time.”

Will this service appeal to do-it-yourself travelers looking to bypass a cultural “person-to-person” tour where the company does all the legwork? Business travel expert Joe Brancatelli told Yahoo Travel that he’s skeptical.

“It's a PR stunt,” he said. “Anyone who really is interested in Cuba would go to a specialist. I'd be shocked if they actually booked any substantial business.”

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If booking on CheapAir, you'll have to enter your reason for visiting Cuba on this page.

Meanwhile, travel industry analyst Henry Harteveldt said he welcomes the news, though CheapAir and customers will need to be mindful of the restrictions.

"I think it’s great that they are doing this," he said. "It makes Cuba more accessible but they have to be careful to still follow the the travel restrictions in place. 

"The risk to the travel agency is that they’re selling these trips, but if they're not really adhering to the true policy, the agency could be fined."

It will work like this: you’ll have to buy two sets of round-trip tickets: one set from anywhere in the U.S. to Mexico, and one set from Mexico to Havana. CheapAir promises to take care of arranging the most convenient connecting flights, though you may need to spend a night in Mexico each way before your flight arrives.

Since the two round-trip flights are unrelated, a change or cancellation to one might inconvenience you a lot more with the other.

The announcement is an incremental change from before, when if you wanted to see Cuba without going on a people-to-people tour, you had to book online from a foreign website such as Cubana.cu, CubaJet, or the Canadian version of Skyscanner, and without the option to add a U.S. departure point. So you’d have to book through two OTAs.

When selecting a flight to Havana on CheapAir, you’ll get a prompt displaying the 12 reasons you’re legally allowed to visit, and you’ll select one. The site explains that you’ll need to re-check your bags in Mexico each way, and that you’ll likely need to stay overnight there. It does offer some lodging options near the airport. Cuba visitors will be required to purchase a visa, which can be had for a small fee in Mexico City.

Other OTA's have been cautious adding Cuba flights, but if CheapAir's initiative succeeds, other could soon follow. A spokeswoman at Expedia told Yahoo Travel the following: "Expanded travel opportunities between the United States and Cuba are a positive development. Expedia looks forward to learning more about the recent initiatives and the new travel opportunities it may herald but has nothing more to share at this time."

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