Cheapair.com became the first online search engine to package flights from the U.S. to Cuba. There are still no commercial flights to Havana from the United States, but the site is packaging together separate flights that route you through Mexico.
It’s not a simple procedure. The flights aren’t “connections” like you’d normally buy. You still have to purchase two tickets (and pay fees separately on each) that won’t be connected in any computer system. If there’s a change in schedule, neither Cheapair.com nor any of the airlines involved will see that you’ve actually booked a connecting flight. Also, if you’re checking bags, you’ll have to recheck them in Mexico. Any cancellations or schedule changes have to be dealt with separately for each ticket.
What’s more, even though travel regulations have been relaxed, you still legally have to prove that you’re traveling to Cuba for one of 12 approved reasons. You don’t need a license anymore, but if you aren’t going for one of those reasons, you will need to pick up your Cuba visa during your changeover in Mexico. A pop-up screen on Cheapair.com explains these stipulations before letting you view fights.
So, how much are flights? We did a little poking around and found that that round trips from JFK or LAX to Havana were running between $1,100 and $1,500 in April. Compare that to about $500 to the Bahamas and the point becomes clear: If you want to be one of the first to book a flight to Cuba from the United States, be prepared to pay a premium.