Cheap flights from Massachusetts to Caribbean

Travel > Caribbean

Looking for cheap flights to Caribbean? We have several useful tools to help you find the flight offer you are looking for. You can enter your search details into the box on the left and compare the current prices of our providers. You can also browse the table below containing the cheapest flights to Caribbean found by Travelgrove users for the next 6 months. Scrolling down you will find one more handy info box with the most recently found Caribbean flight offers. Check the page from top to bottom and pick the flight that suits you best!

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Cheapest flights found for the next 6 months

(click city name to see more / use right arrow to view later months)

Check our newest flight offers to Caribbean:

  • $208American Airlines flight American Airlines 
    Boston, MA (BOS)San Juan, PR (SJU)12/12/201604:55 pm
    San Juan, PR (SJU)Boston, MA (BOS)12/19/201609:00 am check price
  • $288Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)Aguadilla, PR (BQN)04/03/201707:30 pm
    Aguadilla, PR (BQN)Boston, MA (BOS)04/09/201702:00 am check price
  • $312Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)Ponce, PR (PSE)04/03/201707:10 pm
    Ponce, PR (PSE)Boston, MA (BOS)04/09/201702:00 am check price
  • $347Multiple Airlines flight Multiple Airlines 
    Boston, MA (BOS)Santo Domingo, DO (SDQ)01/30/201705:35 am
    Santo Domingo, DO (SDQ)Boston, MA (BOS)02/09/201707:25 am check price
  • $349Spirit Airlines flight Spirit Airlines 
    Boston, MA (BOS)Port Au Prince, HT (PAP)04/04/201708:04 pm
    Port Au Prince, HT (PAP)Boston, MA (BOS)04/12/201710:15 am check price
cheap domestic and international flights

Recently found cheap flight deals

Alaska AirlinesLos Angeles To Albuquerque Alaska Airlines airfares from Los Angeles in March
$261 Depart: 03/21/2017
Return: 04/05/2017

provided by FareDepot

Multiple AirlinesPhiladelphia To Tucson Multiple Airlines airfares from Philadelphia in October
$518 Depart: 10/08/2016
Return: 10/23/2016

provided by FareDepot

Jetblue AirwaysNew York City To Hartford Jetblue Airways airfares from New York City in January
$515 Depart: 01/04/2017
Return: 01/17/2017

provided by FlightHub

LufthansaGreenville/Spartanburg To Bombay Lufthansa airfares from Greenville/Spartanburg in December
$2290 Depart: 12/12/2016
Return: 12/30/2016

provided by FlightHub

Multiple AirlinesBoston To Delhi Multiple Airlines airfares from Boston in December
$1242 Depart: 12/25/2016
Return: 01/18/2017

provided by

Southwest AirlinesSeattle To Harlingen Southwest Airlines airfares from Seattle in December
$636 Depart: 12/16/2016
Return: 12/26/2016

provided by Flightnetwork

Multiple AirlinesNew York City To West Palm Beach Multiple Airlines airfares from New York City in February
$254 Depart: 02/28/2017
Return: 03/08/2017

provided by FareDepot

Alaska AirlinesBaltimore To Miami Alaska Airlines airfares from Baltimore in December
$2475 Depart: 12/18/2016
Return: 12/29/2016

provided by FareDepot

Qatar AirwaysBaltimore To Chennai Qatar Airways airfares from Baltimore in December
$2032 Depart: 12/12/2016
Return: 12/19/2016

provided by


Specify your search details. Browse the cheapest flights from Massachusetts to Caribbean, Caribbean hotel rooms and Massachusetts to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.

San Juan Pictures
  • El Morro - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • San Juan, Puerto Rico - San Juanview
  • El Morro - San Juanview

more Caribbean travel deals

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