Cheap flights from Orlando to Caribbean Islands from $92

The month of February is, on average, the cheapest month to fly to Caribbean Islands from Orlando, with most prices found around $343. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Orlando averaging around $349.

The cheapest day to depart from Orlando to Caribbean Islands is on a Thursday. Travelers who choose to depart for Caribbean Islands on a Thursday will often find tickets for as low as $305. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $325. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Orlando to Caribbean Islands in the evening for as low as $280. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $332. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Orlando to San Juan Luis Munoz Marin Intl for the best Orlando - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $274 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Orlando for as low as $257 on momondo.

There are 4 cabin classes available to choose from on Orlando to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Bahamasair, Delta, and JetBlue are the most popular carriers operating from Orlando to Caribbean Islands

JetBlue, Frontier and Southwest are the top three most popular airlines that fly to Caribbean Islands from Orlando according to our data. JetBlue is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 11 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

As of August 2026, 38 flights take off from Orlando and land in Caribbean Islands each day. The most common flight departure time for this route is 12:00PM, with 41% of daily flights taking off in the afternoon.

269 flights are operational weekly from Orlando to Caribbean Islands as of August 2026. The most popular departure day for this route is Tue, with 19% of flights per week taking off on this day.