After a slow start, the charter flight business from the U.S. to Cuba now is “going well,” according to Jeff Klee, CEO of, which introduced the service in April, becoming the first and only OTA to offer direct charter flights from Miami, New York and Tampa to six cities in Cuba.

Back in February, the company was also the first OTA to offer flights between Cuba and the U.S. on scheduled carriers, but those flights included a connection in a third country such as Mexico, Panama, the Bahamas, the Cayman Islands or Jamaica before finally arriving in Havana.

“Those flights didn’t sell very well,” said Jeff Klee, CEO of CheapAir. “We got inquiries, but the fares were high, connections were bad, and travelers often had to overnight before getting to Cuba.”

CheapAir partnered with Cuba Travel Services, which is licensed by the U.S. Treasury Department’s Office of Foreign Assets Control as an authorized Travel Service Provider to arrange nonstop public charter flights between the U.S. and Cuba.

“The most popular originating city is Miami, with flights on American, Sun Country and Swift Air,” Klee said.

JetBlue’s weekly nonstop from New York's Kennedy Airport, which launched July 3, is gaining ground, as is the Sun Country weekly charter from Kennedy.

Roundtrip fares from Miami are $400 and up, while New York flights are closer to $800, Klee said, adding that “CheapAir wants to add more flights, and we’re in talks with some carriers now.”

Before booking a charter flight, travelers have to indicate on a U.S. government form their reason for travel to Cuba. CheapAir passes the manifest information to Cuba Travel Services.

“The two most popular categories that are checked on the form are travel for educational reasons or professional research,” Klee said. “It’s sort of the honor system. Travelers have to keep their travel documents for five years in case anyone checks.”

CheapAir owns this market for now, but Klee figures it won’t stay that way for long. Travelport is readying itself for scheduled airlines’ U.S-Cuba flights, following its announcement in late June of new GDS software that enables U.S.-based travel agencies to sell and book flights to and from Cuba for authorized travelers. Travelport also is considering incorporating direct charter flights if demand increases.


From Our Partners

2021 Family Expo
Family Travel Expo
Register Now
Air Astana 1366
Air Astana
Read More
2021 Caesars Webinar
Watch Now

JDS Travel News JDS Viewpoints JDS Africa/MI