Cheap flights from Massachusetts to Caribbean Islands from $107

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Massachusetts, with most prices found around $453. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Massachusetts averaging around $456.

The cheapest day to depart from Massachusetts 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 $362. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $397. 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 Massachusetts to Caribbean Islands in the afternoon for as low as $348. 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 $387. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Boston Logan Intl to San Juan Luis Munoz Marin Intl for the best Massachusetts - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $342 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Massachusetts for as low as $285 on momondo.

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

United Airlines, Delta, and Southwest are the most popular carriers operating from Massachusetts to Caribbean Islands

JetBlue, Delta and American Airlines are the top three most popular airlines that fly to Caribbean Islands from Massachusetts according to our data. JetBlue is the first choice among our users, with 70% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 11 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

As of June 2026, there are 21 flights per day flying from Massachusetts to Caribbean Islands. The most common time of day flights depart is 9:00PM, with 47% of flights taking off at noon.

The number of flights available between Massachusetts and Caribbean Islands is 148 per week as of June 2026. The most frequent departure day is Mon, with 19% of weekly flights leaving on this day.