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:

  • $120Spirit Airlines flight Spirit Airlines 
    Boston, MA (BOS)St. Thomas Island, VI (STT)10/20/202106:53 pm
    St. Thomas Island, VI (STT)Boston, MA (BOS)11/01/202103:50 pm check price
  • $201Spirit Airlines flight Spirit Airlines 
    Boston, MA (BOS)St. Croix Island, VI (STX)11/29/202105:20 am
    St. Croix Island, VI (STX)Boston, MA (BOS)12/05/202106:36 pm check price
  • $752Air Canada flight Air Canada 
    Boston, MA (BOS)Trinidad, TT (POS)12/01/202106:45 pm
    Trinidad, TT (POS)Boston, MA (BOS)12/21/202105:05 pm check price
  • $763Air Canada flight Air Canada 
    Boston, MA (BOS)Hamilton, BM (BDA)06/18/202203:55 pm
    Hamilton, BM (BDA)Boston, MA (BOS)06/25/202202:30 pm check price
  • $819Multiple Airlines flight Multiple Airlines 
    Boston, MA (BOS)Aruba, AW (AUA)01/26/202208:40 pm
    Aruba, AW (AUA)Boston, MA (BOS)02/15/202204:30 pm check price
cheap domestic and international flights

Recently found cheap flight deals

Multiple AirlinesLas Vegas To Saint Petersburg Multiple Airlines airfares from Las Vegas in August
$1070 Depart: 08/24/2021
Return: 09/08/2021

provided by

Thy Turkish AirlinesSan Francisco To Marseille Thy Turkish Airlines airfares from San Francisco in September
$959 Depart: 09/18/2021
Return: 09/30/2021

provided by

Multiple AirlinesLouisville To Paris Multiple Airlines airfares from Louisville in October
$896 Depart: 10/12/2021
Return: 10/20/2021

provided by

Frontier AirlinesDetroit To Tulsa Frontier Airlines airfares from Detroit in August
$620 Depart: 08/04/2021
Return: 08/19/2021

provided by

Multiple AirlinesToronto To Bermuda Multiple Airlines airfares from Toronto in September
$1901 Depart: 09/12/2021
Return: 09/24/2021

provided by

Multiple AirlinesTampa To Washington DC Multiple Airlines airfares from Tampa in December
$616 Depart: 12/28/2021
Return: 01/05/2022

provided by

Spirit AirlinesCharleston To Las Vegas Spirit Airlines airfares from Charleston in January
$588 Depart: 01/11/2022
Return: 01/18/2022

provided by

Multiple AirlinesOrange County To Bombay Multiple Airlines airfares from Orange County in September
$784 Depart: 09/10/2021
Return: 09/18/2021

provided by

British AirwaysSan Antonio To Tirana British Airways airfares from San Antonio in December
$1651 Depart: 12/21/2021
Return: 01/04/2022

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.

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