Cheap flights from Massachusetts to Caribbean from $107

In general, September is the cheapest month to fly from Massachusetts to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $403. If you don’t want to visit Caribbean in September, then you should wait until January to fly from Massachusetts, when ticket prices are also cheap, with an average price of $423.

The cheapest day to depart from Massachusetts to Caribbean is on a Monday when prices can be found 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.

In the afternoon is the cheapest time of day to fly from Massachusetts to Caribbean when you can find flight prices for as low as $348. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $387.

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

You are more likely to see cheaper flights to Caribbean from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean 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 from Massachusetts for as low as $285 on momondo.

There are 4 cabin classes available to choose from on Massachusetts to Caribbean 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 JetBlue are the most popular carriers operating from Massachusetts to Caribbean

JetBlue, Delta and American Airlines are the top three most popular airlines that fly to Caribbean 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. Keep in mind that there are 11 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

The number of flights available between Massachusetts and Caribbean is 21 per day as of June 2026. The most frequent departure time is 9:00PM, with 47% of daily flights leaving at noon.

As of June 2026, there are 148 flights per week flying from Massachusetts to Caribbean. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.