Cheap flights from Washington, D.C. to Caribbean from $133

In general, January 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 $476. If you don’t want to visit Caribbean in January, then you should wait until February to fly from Washington, D.C., when ticket prices are also cheap, with an average price of $494.

The cheapest day to depart from Washington, D.C. to Caribbean is on a Monday when prices can be found for as low as $407. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $525. 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 $301. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $505.

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 $444 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 $385 on momondo.

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

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

United Airlines, Frontier and JetBlue 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 37% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 9 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

Historically, on average around 19% of flights between Washington, D.C. and Caribbean have experienced a delay on any given week. The average delay length over the past 12 months has been 132 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights in the evening have, in the past, seen delays more frequently in comparison.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 16% of their flights experiencing any sort of delay.

As of November 2026, there are 9 flights per day flying from Washington, D.C. to Caribbean. The most common time of day flights depart is 8:00AM, with 62% of flights taking off at noon.

As of November 2026, there are 66 flights per week flying from Washington, D.C. to Caribbean. The most common day of the week flights depart is Wed, with 15% of flights taking off on this day.