Cheap flights from Orlando Airport to Caribbean Islands from $74

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Orlando Airport, with most prices found around $356. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Orlando Airport averaging around $364.

The cheapest day to depart from Orlando Airport to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $304. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $321. 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 Airport to Caribbean Islands in the evening for as low as $279. 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 $330. 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 Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $273 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 Airport for as low as $257 on momondo.

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

Frontier, Southwest, and American Airlines 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 Airport according to our data. JetBlue is the first choice among our users, with 46% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 9 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, 35 flights take off from Orlando Airport and land in Caribbean Islands each day. The most common flight departure time for this route is 1:00PM, with 38% of daily flights taking off in the afternoon.

As of August 2026, there are 251 flights per week flying from Orlando Airport to Caribbean Islands. The most common day of the week flights depart is Fri, with 21% of flights taking off on this day.