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:

  • $305Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)Hamilton, BM (BDA)04/03/201803:01 pm
    Hamilton, BM (BDA)Boston, MA (BOS)04/13/201803:07 pm check price
  • $343Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)St. Thomas Island, VI (STT)04/07/201810:28 pm
    St. Thomas Island, VI (STT)Boston, MA (BOS)04/12/201802:04 pm check price
  • $353Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)San Juan, PR (SJU)04/15/201808:54 pm
    San Juan, PR (SJU)Boston, MA (BOS)04/24/201803:21 am check price
  • $359Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)St. Croix Island, VI (STX)04/07/201810:28 pm
    St. Croix Island, VI (STX)Boston, MA (BOS)04/12/201801:14 pm check price
  • $382Copa Air flight Copa Air 
    Boston, MA (BOS)Santo Domingo, DO (SDQ)04/16/201803:24 pm
    Santo Domingo, DO (SDQ)Boston, MA (BOS)04/28/201806:04 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesHouston To Bologna Multiple Airlines airfares from Houston in February
$6754 Depart: 02/13/2018
Return: 02/27/2018

provided by Travelgrove

Multiple AirlinesDallas To Brownsville Multiple Airlines airfares from Dallas in November
$872 Depart: 11/16/2017
Return: 11/24/2017

provided by FlyFar

United AirlinesDurham To Rome United Airlines airfares from Durham in June
$1555 Depart: 06/29/2018
Return: 07/15/2018

provided by Travelgrove

Multiple AirlinesDenver To Bellingham Multiple Airlines airfares from Denver in March
$511 Depart: 03/29/2018
Return: 04/05/2018

provided by Flightnetwork

Multiple AirlinesTulsa To Chicago Multiple Airlines airfares from Tulsa in March
$1493 Depart: 03/24/2018
Return: 04/01/2018

provided by FlyFar

United AirlinesTampa To Frankfurt United Airlines airfares from Tampa in July
$1148 Depart: 07/06/2018
Return: 07/31/2018

provided by Travelgrove

Multiple AirlinesBaltimore To Johannesburg Multiple Airlines airfares from Baltimore in July
$2353 Depart: 07/18/2018
Return: 07/31/2018

provided by

Multiple AirlinesLas Vegas To Monterey Multiple Airlines airfares from Las Vegas in March
$580 Depart: 03/24/2018
Return: 03/30/2018

provided by Flightnetwork

Copa AirHartford To Port Au Prince Copa Air airfares from Hartford in March
$3335 Depart: 03/28/2018
Return: 04/11/2018

provided by FlyFar


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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