Cheap flights from Washington, D.C. to Caribbean from $115

In general, October is the cheapest month to fly from Washington, D.C. to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $452. If you don’t want to visit Caribbean in October, then you should wait until August to fly from Washington, D.C., when ticket prices are also cheap, with an average price of $486.

The cheapest day to depart from Washington, D.C. to Caribbean is on a Sunday when prices can be found for as low as $361. If your travel schedule is flexible, try to avoid departing on a Wednesday because tickets tend to average around $488. 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 Washington, D.C. to Caribbean when you can find flight prices for as low as $344. 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 $455.

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

You are more likely to see cheaper flights to Caribbean from Washington, D.C. when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $394 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Washington, D.C. for as low as $335 on momondo.

JetBlue, American Airlines, and Southwest are the most popular carriers operating from Washington, D.C. to Caribbean

United Airlines, Frontier and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Washington, D.C. according to our data. United Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 10 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

As of May 2026, there are 13 flights per day flying from Washington, D.C. to Caribbean. The most common time of day flights depart is 8:00AM, with 69% of flights taking off at noon.

As of May 2026, there are 96 flights per week flying from Washington, D.C. to Caribbean. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.