Cheap flights from Washington, D.C. to Caribbean Islands from $127

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Washington, D.C., with most prices found around $523. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Washington, D.C. averaging around $547.

The cheapest day to depart from Washington, D.C. to Caribbean Islands is on a Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $412. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $492. 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 Washington, D.C. to Caribbean Islands in the evening for as low as $341. 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 in the morning because they tend to be around $485. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Baltimore/Washington to San Juan Luis Munoz Marin Intl for the best Washington, D.C. - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $431 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Washington, D.C. for as low as $367 on momondo.

There are 4 cabin classes available to choose from on Washington, D.C. 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, JetBlue, and United Airlines are the most popular carriers operating from Washington, D.C. to Caribbean Islands

United Airlines, Frontier and JetBlue are the top three most popular airlines that fly to Caribbean Islands from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 36% 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.

The number of flights available between Washington, D.C. and Caribbean Islands is 9 per day as of August 2026. The most frequent departure time is 8:00AM, with 81% of daily flights leaving at noon.

63 flights are operational weekly from Washington, D.C. to Caribbean Islands as of August 2026. The most popular departure day for this route is Sat, with 21% of flights per week taking off on this day.