Cheap flights from Massachusetts to Caribbean

Travel > Caribbean

The place to head for complete relaxation for your next vacation is none other than Montego Bay, Jamaica. Montego Bay is a hot tourist spot, and has been such since 1924. And as proof of this increased tourism in Montego Bay, you find a bustling community here at all times.... (read more in our Montego Bay Sightseeing)

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Cheapest flights found for the next 6 months

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Check our newest flight offers to Caribbean:

  • $238Multiple Airlines flight Multiple Airlines 
    Boston, MA (BOS)San Juan, PR (SJU)02/01/201709:25 pm
    San Juan, PR (SJU)Boston, MA (BOS)02/16/201703:10 pm check price
  • $275American Airlines flight American Airlines 
    Boston, MA (BOS)Hamilton, BM (BDA)04/03/201705:00 pm
    Hamilton, BM (BDA)Boston, MA (BOS)04/09/201703:15 pm check price
  • $293Jetblue Airways flight Jetblue Airways 
    Boston, MA (BOS)Ponce, PR (PSE)02/01/201708:25 am
    Ponce, PR (PSE)Boston, MA (BOS)02/16/201705:50 am check price
  • $351Spirit Airlines flight Spirit Airlines 
    Boston, MA (BOS)St. Thomas Island, VI (STT)01/24/201705:00 am
    St. Thomas Island, VI (STT)Boston, MA (BOS)01/31/201705:17 pm check price
  • $358Spirit Airlines flight Spirit Airlines 
    Boston, MA (BOS)Saint Maarten, AN (SXM)01/21/201705:00 am
    Saint Maarten, AN (SXM)Boston, MA (BOS)01/28/201703:51 pm check price
cheap domestic and international flights

Recently found cheap flight deals

American AirlinesNewark To Toronto American Airlines airfares from Newark in January
$234 Depart: 01/25/2017
Return: 02/01/2017

provided by FareDepot

Multiple AirlinesHouston To Lahore Multiple Airlines airfares from Houston in January
$1210 Depart: 01/18/2017
Return: 01/25/2017

provided by

Multiple AirlinesFort Lauderdale To Cozumel Multiple Airlines airfares from Fort Lauderdale in February
$1791 Depart: 02/06/2017
Return: 02/16/2017

provided by FareDepot

Southwest AirlinesProvidence To Fort Myers Southwest Airlines airfares from Providence in February
$648 Depart: 02/18/2017
Return: 02/25/2017

provided by Flightnetwork

Jetblue AirwaysFort Lauderdale To Quito Jetblue Airways airfares from Fort Lauderdale in February
$375 Depart: 02/21/2017
Return: 03/08/2017

provided by FlightHub

Multiple AirlinesRochester To Baltimore Multiple Airlines airfares from Rochester in May
$325 Depart: 05/16/2017
Return: 06/07/2017

provided by FareDepot

Multiple AirlinesDetroit To Maui Multiple Airlines airfares from Detroit in March
$1478 Depart: 03/28/2017
Return: 04/03/2017

provided by Flightnetwork

Multiple AirlinesHouston To Caracas Multiple Airlines airfares from Houston in December
$3897 Depart: 12/13/2016
Return: 12/27/2016

provided by FareDepot

LufthansaOttawa To Zagreb Lufthansa airfares from Ottawa in February
$763 Depart: 02/23/2017
Return: 03/02/2017

provided by FlyFar


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

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