Cheap flights from Caribbean to Boston from $100

In general, February is the cheapest month to fly from Caribbean to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $203. If you aren’t able to travel during the month of February, then book flights to Boston from Caribbean during April instead. Flights to Boston in April, while not as cheap as those in February, still average around $232.

The cheapest day to depart from Caribbean to Boston is on a Friday when prices can be found for as low as $273. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $347.

According to our data, the cheapest time of day to fly to Boston is in the afternoon. momondo users have found flights departing from Caribbean to Boston in the afternoon for as low as $255. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Boston, so prices are often more expensive at around $296 per ticket.

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

You are more likely to see cheaper flights to Boston from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $267 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Caribbean for as low as $243 on momondo.

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

Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Caribbean to Boston Logan Intl

JetBlue, Delta and Spirit Airlines are the top three most popular airlines that fly to Boston from Caribbean according to our data. JetBlue is the first choice among our users, with 72% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 7 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

As of March 2026, there are 43 flights per day flying from Caribbean to Boston. The most common time of day flights depart is 2:00PM, with 61% of flights taking off in the afternoon.

304 flights are operational weekly from Caribbean to Boston as of March 2026. The most popular departure day for this route is Sun, with 16% of flights per week taking off on this day.