Cheap flights from Massachusetts to Jamaica from $142

The cheapest month to fly to Jamaica from Massachusetts is in February. Flight prices, which tend to average around $468, are often lower during this time because this is during the off-season. If you aren’t able to travel to Jamaica during the month of February, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $469.

The cheapest day to depart on your flight to Jamaica is on a Wednesday when prices can be found for as low as $447. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $570.

Fly from Boston Logan Intl to Montego Bay Sangster Intl for the best Massachusetts - Jamaica flight prices

You are more likely to see cheaper flights to Jamaica from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Jamaica for around $515 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Jamaica from Massachusetts for as low as $470 on momondo.

There are 3 cabin classes available to choose from on Massachusetts to Jamaica flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 4% on your flight if you consider stops on a Massachusetts to Jamaica flight.

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

JetBlue, American Airlines and Delta are the top three most popular airlines that fly to Jamaica from Massachusetts according to our data. JetBlue is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Jamaica. Keep in mind that there are 7 different airlines that fly to Jamaica on a routine basis, so you have a few additional options to choose from.

3 flights are operational weekly from Massachusetts to Jamaica as of August 2026. The most popular departure day for this route is Thu, with 33% of flights per week taking off on this day.

Flight times from Massachusetts to Jamaica vary, but if you’re flying out of Boston and flying into Montego Bay (one of the most popular routes), then the duration is 4h 15m on average. Another popular route from Massachusetts to Jamaica is flying from Worcester to Montego Bay, which will take roughly 18h 55m. Keep in mind that layovers or delays could extend your travel time.