Cheap flights from Orlando to Caribbean from $55

In general, February is the cheapest month to fly from Orlando to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $270. If you don’t want to visit Caribbean in February, then you should wait until January to fly from Orlando, when ticket prices are also cheap, with an average price of $295.

The cheapest day to depart from Orlando to Caribbean is on a Thursday when prices can be found for as low as $301. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $319. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

In the evening is the cheapest time of day to fly from Orlando to Caribbean when you can find flight prices for as low as $276. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the afternoon are often more expensive with an average ticket price of $323.

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

You are more likely to see cheaper flights to Caribbean from Orlando when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $270 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Orlando for as low as $256 on momondo.

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

Frontier, JetBlue, and Arajet are the most popular carriers operating from Orlando to Caribbean

JetBlue, Frontier and Southwest are the top three most popular airlines that fly to Caribbean from Orlando according to our data. JetBlue is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 11 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

As of October 2026, there are 11 flights per day flying from Orlando to Caribbean. The most common time of day flights depart is 10:00AM, with 46% of flights taking off at noon.

As of October 2026, there are 78 flights per week flying from Orlando to Caribbean. The most common day of the week flights depart is Wed, with 45% of flights taking off on this day.