One of the reasons for the ongoing popularity of Caribbean vacations is the ease of getting there. A shorter flight than Hawaii, and cheaper too, the Caribbean islands are the shortest trips to exotic beach locales for most Americans. The wide variety of islands is reflected in the wide variety of prices you'll pay, depending on which destination you choose to fly into.

The most popular Caribbean flight lands in Jamaica. With numerous airports on the island, the locale is perfect for both connecting flights and non-stop flights from many U.S. locations, especially the east coast. Though many visitors choose to stay in Jamaica, AirJamaica provides cheap Caribbean flights, connecting the islands like never before. Also, they are one of the leading providers for Caribbean airpasses – a service in which you pay a flat fee and are given unlimited air travel throughout a select period of time, normally one month. This allows you to pick and choose your island destinations with abandon and affords you the freedom to spontaneously fly from one nation to another. These airpasses are extremely popular for those on extended vacations, those who want to see the most the Caribbean has to offer.

Cheap Caribbean flights can also land you in the Virgin Islands or Aruba. Despite Aruba's reputation as a pricey island, airfare there is surprisingly cheap. In fact, if you are traveling to the Windward or Southern Islands, all the cheap flights to the Caribbean will land you in Aruba before connecting elsewhere. Curacao and Trinidad are the only other locations in this area that may be considered inexpensive, but that has more to do with your personal definition of the word.

Caribbean Map

By far the best home for cheap flights to the Caribbean is San Juan, Puerto Rico. Since it is usually passed up as a tourist destination, in favor of the more exotic or tourist-driven islands, airfare to Puerto Rico is significantly cheaper than many of the neighboring islands, even in the high-season. For less than $500, you can arrive in Puerto Rico. Not only that, but its airport has a number of island-hopping flights, making it a good starting point for any multi-national tour of the Caribbean.

A final note on cheap flights to the Caribbean – if you want one to Cuba, you're out of luck. Thanks to misguided and unfortunate legislation passed by the U.S. Government, United States airlines are not allowed to fly into Havana (not counting a couple from Miami and New York City). You cannot book a flight to Cuba on any Internet website – your only choice is to fly to another country and then book a flight with a carrier based in that country. The most used are Mexican or Dominican airlines.