Cheap flights from Boston to Caribbean Islands from $113

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Boston, with most prices found around $453. The month of May is another great option to travel to Caribbean Islands, with average flight prices from Boston averaging around $457.

The cheapest day to depart from Boston to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $359. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $394. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Boston to Caribbean Islands in the afternoon for as low as $342. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $382. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Boston Logan Intl to Santo Domingo Las Americas for the best Boston Logan Intl - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $334 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Boston for as low as $285 on momondo.

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

United Airlines, JetBlue, and Delta are the most popular carriers operating from Boston Logan Intl to Caribbean Islands

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

The number of flights available between Boston and Caribbean Islands is 12 per day as of June 2026. The most frequent departure time is 5:00PM, with 45% of daily flights leaving at noon.

As of June 2026, 84 flights take off from Boston and land in Caribbean Islands each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.