Cheap flights from Caribbean to Massachusetts from $96

In general, February 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 $208. If you aren’t able to travel to Massachusetts during the month of February, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $233.

According to our data, Friday is the cheapest day to fly to Massachusetts from Caribbean. The lowest ticket price found for a Friday departure recently was $273. 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, Monday 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 $347.

Our data shows that the cheapest Caribbean to Massachusetts flights are usually those with departure times in the afternoon. Our users have found flights to Massachusetts in the afternoon for as low as $255. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $296 on average. Flights to Massachusetts from Caribbean in the morning 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 $267 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 $240 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.

Frontier, Spirit Airlines, and JetBlue are the most popular carriers operating from Caribbean to Massachusetts

JetBlue, Delta and Spirit Airlines 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 7 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 39 per day as of February 2026. The most frequent departure time is 6:00AM, with 46% of daily flights leaving in the afternoon.

As of February 2026, there are 278 flights per week flying from Caribbean to Massachusetts. The most common day of the week flights depart is Thu, with 19% of flights taking off on this day.