Cheap flights from Caribbean to Massachusetts from $124

In general, November is the cheapest month to fly from Caribbean to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $346. If you aren’t able to travel to Massachusetts during the month of November, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $353.

According to our data, Thursday is the cheapest day to fly to Massachusetts from Caribbean. The lowest ticket price found for a Thursday departure recently was $309. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $448.

Our data shows that the cheapest Caribbean to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $279. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $363 on average. Flights to Massachusetts from Caribbean at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

You are more likely to see cheaper flights to Massachusetts from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $294 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Caribbean for as low as $263 on momondo.

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

Southwest, Delta, and JetBlue are the most popular carriers operating from Caribbean to Massachusetts

JetBlue, Delta and Arajet are the top three most popular airlines that fly to Massachusetts from Caribbean 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 Massachusetts. Keep in mind that there are 6 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

The number of flights available between Caribbean and Massachusetts is 25 per day as of June 2026. The most frequent departure time is 6:00AM, with 67% of daily flights leaving at noon.

As of June 2026, there are 179 flights per week flying from Caribbean to Massachusetts. The most common day of the week flights depart is Thu, with 18% of flights taking off on this day.