Cheap flights from District of Columbia to Caribbean from $136

In general, October is the cheapest month to fly from District of Columbia to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $455. If you don’t want to visit Caribbean in October, then you should wait until August to fly from District of Columbia, when ticket prices are also cheap, with an average price of $476.

The cheapest day to depart from District of Columbia to Caribbean is on a Sunday when prices can be found for as low as $372. 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 District of Columbia 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 $465.

Fly from Baltimore/Washington to San Juan Luis Munoz Marin Intl for the best District of Columbia - Caribbean flight prices

You are more likely to see cheaper flights to Caribbean from District of Columbia when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $406 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from District of Columbia for as low as $316 on momondo.

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

Southwest, United Airlines, and JetBlue are the most popular carriers operating from District of Columbia to Caribbean

United Airlines, Frontier and American Airlines are the top three most popular airlines that fly to Caribbean from District of Columbia according to our data. United Airlines is the first choice among our users, with 35% 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.

As of June 2026, 9 flights take off from District of Columbia and land in Caribbean each day. The most common flight departure time for this route is 8:00AM, with 59% of daily flights taking off at noon.

69 flights are operational weekly from District of Columbia to Caribbean as of June 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.