Cheap flights from Maryland to Caribbean Islands from $62

The month of July is, on average, the cheapest month to fly to Caribbean Islands from Maryland, with most prices found around $294. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Maryland averaging around $297.

The cheapest day to depart from Maryland to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $267. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $324. 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 afternoon. momondo users have found flights departing from Maryland to Caribbean Islands in the afternoon for as low as $283. 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 evening because they tend to be around $371. 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 Maryland - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Maryland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Maryland for as low as $339 on momondo.

There are 4 cabin classes available to choose from on Maryland 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, Spirit Airlines, and American Airlines are the most popular carriers operating from Maryland to Caribbean Islands

Spirit Airlines, Southwest and American Airlines are the top three most popular airlines that fly to Caribbean Islands from Maryland according to our data. Spirit Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 8 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 Maryland and Caribbean Islands is 25 per day as of February 2026. The most frequent departure time is 8:00AM, with 83% of daily flights leaving at noon.

181 flights are operational weekly from Maryland to Caribbean Islands as of February 2026. The most popular departure day for this route is Sat, with 20% of flights per week taking off on this day.