Cheap flights from the United States to Caribbean from $69

In general, January is the cheapest month to fly from United States to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $439. If you don’t want to visit Caribbean in January, then you should wait until May to fly from United States, when ticket prices are also cheap, with an average price of $475.

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

You are more likely to see cheaper flights to Caribbean from United States when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $354 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from United States for as low as $296 on momondo.

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

Southwest, JetBlue, and American Airlines are the most popular carriers operating from United States to Caribbean

JetBlue, American Airlines and Frontier are the top three most popular airlines that fly to Caribbean from United States according to our data. JetBlue is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 23 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 61 flights per day flying from United States to Caribbean. The most common time of day flights depart is 8:00AM, with 55% of flights taking off at noon.

As of October 2026, 433 flights take off from United States and land in Caribbean each week. The most common flight departure day for this route is Fri, with 27% of weekly flights taking off on this day.