$93+ Cheap flights from Caribbean to Massachusetts
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Mar 15 — Mar 221
1 adult, Economy
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Find cheap flights from Caribbean to Massachusetts with Cheapflights
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Cheapest flights from Caribbean to MassachusettsExplore the most affordable flight options available from Caribbean to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.
Explore the most affordable flight options available from Caribbean to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.
This Orbitz deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Sat 2/288:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
SJU
- BOS
Nonstop4h 21m
Multiple Airlines
Mon 3/210:04 am
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Thu 3/58:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Sun 3/18:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$122
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$129
This Orbitz deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Sun 2/225:27 am
BOS
- SJU
1 stop9h 04m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$130
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Tue 2/245:27 am
BOS
- SJU
1 stop9h 04m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$132
This Expedia deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$133
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- BOS
Nonstop4h 19m
Frontier
Tue 3/36:00 am
BOS
- SJU
1 stop8h 06m
Frontier
Deal found 2/10![Frontier logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Mon 3/27:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/12![Frontier logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/283:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Mon 3/27:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/12![Frontier logo]()
$165
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Sun 3/811:10 am
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/10![Frontier logo]()
$166
Best flights from Caribbean to MassachusettsDiscover carefully curated flight deals from Caribbean to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 13, 2026.
Discover carefully curated flight deals from Caribbean to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/46:00 am
SJU
- BOS
1 stop6h 48m
Spirit Airlines
Tue 3/108:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Sun 3/811:10 am
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/13![Frontier logo]()
$188
This Flysmarter deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/263:20 pm
AUA
- BOS
Nonstop5h 04m
JetBlue
Fri 4/36:30 am
BOS
- AUA
Nonstop4h 40m
JetBlue
Deal found 2/11![JetBlue logo]()
$230
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/262:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Sun 3/298:40 am
BOS
- STT
Nonstop4h 03m
Delta
Deal found 2/12![Delta logo]()
$241
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/224:30 pm
AUA
- BOS
2 stops20h 59m
United Airlines
Mon 4/276:00 am
BOS
- AUA
1 stop8h 00m
United Airlines
Deal found 2/12![United Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:25 pm
STT
- BOS
2 stops10h 29m
American Airlines
Sun 4/266:00 am
BOS
- STT
2 stops10h 15m
American Airlines
Deal found 2/11![American Airlines logo]()
$250
This Vliegwinkel deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/263:40 pm
AUA
- BOS
1 stop8h 19m
Multiple Airlines
Fri 4/36:30 am
BOS
- AUA
Nonstop4h 40m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$253
This eDestinos deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:30 am
SDQ
- BOS
Nonstop4h 15m
Arajet
Sun 5/3110:20 pm
BOS
- SDQ
Nonstop4h 15m
Arajet
Deal found 2/13![Arajet logo]()
$301
This Spirit deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Sun 3/88:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$171
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/2311:59 pm
SJU
- BDL
Nonstop4h 06m
Frontier
Mon 4/278:08 pm
BDL
- SJU
1 stop13h 46m
Frontier
Deal found 2/10![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Wed 3/183:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/252:41 pm
STT
- BOS
1 stop5h 48m
JetBlue
Mon 3/309:00 am
BOS
- STT
Nonstop4h 04m
JetBlue
Deal found 2/12![JetBlue logo]()
$240
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:30 pm
SJU
- BOS
Nonstop4h 23m
Delta
Tue 5/198:20 am
BOS
- SJU
Nonstop4h 08m
Delta
Deal found 2/10![Delta logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/212:59 am
SJU
- BDL
Nonstop4h 06m
Frontier
Mon 4/66:00 am
BDL
- SJU
Nonstop3h 53m
Frontier
Deal found 2/13![Frontier logo]()
$221
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:30 pm
STT
- BOS
1 stop8h 37m
American Airlines
Wed 4/226:00 am
BOS
- STT
2 stops8h 49m
American Airlines
Deal found 2/12![American Airlines logo]()
$250
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:30 pm
AUA
- BOS
2 stops16h 55m
United Airlines
Sat 5/210:00 am
BOS
- AUA
2 stops26h 40m
United Airlines
Deal found 2/13![United Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:53 am
SJU
- BDL
1 stop7h 44m
Multiple Airlines
Mon 3/27:13 pm
BDL
- SJU
2 stops13h 41m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$264
This JetBlue deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/262:12 pm
STT
- BOS
1 stop5h 48m
JetBlue
Mon 3/309:00 am
BOS
- STT
Nonstop4h 04m
JetBlue
Deal found 2/12![JetBlue logo]()
$241
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:33 pm
SJU
- BOS
Nonstop4h 11m
Delta
Wed 8/128:10 am
BOS
- SJU
Nonstop4h 06m
Delta
Deal found 2/12![Delta logo]()
$243
This Priceline deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/53:16 am
SJU
- BDL
1 stop10h 37m
Frontier
Sun 4/122:55 pm
BDL
- SJU
1 stop9h 57m
Frontier
Deal found 2/13![Frontier logo]()
$234
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:00 am
SJU
- BDL
2 stops8h 37m
United Airlines
Mon 4/276:00 am
BDL
- SJU
1 stop8h 44m
United Airlines
Deal found 2/13![United Airlines logo]()
$262
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:44 pm
SJU
- BDL
1 stop9h 33m
American Airlines
Sun 3/88:25 am
BDL
- SJU
1 stop15h 27m
American Airlines
Deal found 2/13![American Airlines logo]()
$262
This Expedia deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/183:55 am
SDQ
- BOS
Nonstop4h 05m
Multiple Airlines
Sun 4/1910:20 pm
BOS
- SDQ
Nonstop4h 15m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$265
This JetBlue deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:56 pm
STT
- BOS
1 stop5h 47m
JetBlue
Mon 4/2710:01 am
BOS
- STT
Nonstop4h 00m
JetBlue
Deal found 2/11![JetBlue logo]()
$241
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:36 pm
STT
- BOS
1 stop8h 42m
Spirit Airlines
Wed 4/225:40 am
BOS
- STT
1 stop9h 50m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$244
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/253:55 pm
STT
- BOS
1 stop6h 59m
Delta
Sun 3/298:40 am
BOS
- STT
Nonstop4h 03m
Delta
Deal found 2/12![Delta logo]()
$246
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:25 pm
SJU
- BOS
Nonstop4h 00m
JetBlue
Sun 5/106:10 pm
BOS
- SJU
Nonstop4h 02m
JetBlue
Deal found 2/11![JetBlue logo]()
$242
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:30 pm
SJU
- BOS
Nonstop4h 23m
Delta
Sun 5/105:40 am
BOS
- SJU
1 stop7h 39m
Delta
Deal found 2/10![Delta logo]()
$248
This Priceline deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/123:40 pm
AUA
- BOS
1 stop8h 19m
Multiple Airlines
Tue 3/2410:58 am
BOS
- AUA
Nonstop4h 52m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$278
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/2612:35 pm
AUA
- BOS
1 stop10h 05m
American Airlines
Wed 4/16:30 am
BOS
- AUA
1 stop9h 10m
American Airlines
Deal found 2/13![American Airlines logo]()
$278
Last-minute flights from Caribbean to MassachusettsDiscover last-minute flight deals from Caribbean to Massachusetts. Data last updated February 13, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Massachusetts. Data last updated February 13, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Tue 2/245:27 am
BOS
- SJU
1 stop9h 04m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$132
This Orbitz deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Sun 2/225:27 am
BOS
- SJU
1 stop9h 04m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$130
This Orbitz deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Sat 2/288:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$119
This Expedia deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
SJU
- BOS
Nonstop4h 21m
Multiple Airlines
Mon 3/210:04 am
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Tue 3/38:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$121
This iWofly deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure iWofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Sun 3/18:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$122
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$129
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- BOS
Nonstop4h 19m
Frontier
Tue 3/36:00 am
BOS
- SJU
1 stop8h 06m
Frontier
Deal found 2/10![Frontier logo]()
$137
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/263:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Mon 3/27:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/12![Frontier logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/283:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Mon 3/27:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/12![Frontier logo]()
$165
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/53:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Sun 3/811:10 am
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/10![Frontier logo]()
$166
One-way flights from Caribbean to MassachusettsSearch for one-way flight options from Caribbean to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
Search for one-way flight options from Caribbean to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 13, 2026.
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/244:11 pm
SJU
- BOS
1 stop10h 02m
Frontier
Deal found 2/10![Frontier logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:36 pm
SJU
- BOS
1 stop8h 23m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$94
This Frontier deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Frontier
Deal found 2/10![Frontier logo]()
$95
This Spirit deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$96
This FlightHub deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:25 pm
SJU
- BOS
1 stop16h 41m
Frontier
Deal found 2/10![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/87:00 am
SJU
- BOS
1 stop9h 54m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:52 am
SJU
- BOS
1 stop13h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1010:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:35 pm
STT
- BOS
1 stop7h 24m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:52 am
SJU
- BOS
1 stop13h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/104:40 pm
STT
- BOS
1 stop7h 04m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/103:08 am
SJU
- BOS
1 stop7h 13m
Frontier
Deal found 2/11![Frontier logo]()
$104
Find flight deals from Caribbean to Massachusetts
Keep the following information in mind while searching for Caribbean to Massachusetts flight deals. Data was last updated February 13, 2026.
Round-trip from | $119 (Orbitz) |
|---|---|
One-way from | $93 (Super.com) |
Popular in | July |
Cheapest in | February |
Average price | $205 |
Good round-trip deal | $140 or less |
Good one-way deal | $179 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Caribbean to Massachusetts that are best for you.
Fly from
Caribbean
Fly to
Massachusetts
Route
Depart
Return
Price
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Wed 3/4
6:00 am-11:48 am
1 stop6h 48m
Boston Logan Intl
Tue 3/10
8:01 pm-12:08 am
Nonstop4h 07m
$167
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Wed 3/4
11:22 am-2:43 pm
Nonstop4h 21m
Boston Logan Intl
Sun 3/8
8:01 pm-12:08 am
Nonstop4h 07m
$171
San JuanHartford
SJU - BDL
SJUBDL
San Juan Luis Munoz Marin Intl
Thu 3/5
3:55 pm-7:10 pm
Nonstop4h 15m
Hartford Bradley Intl
Sun 3/8
11:10 am-3:01 pm
Nonstop3h 51m
$188
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Wed 3/11
10:22 am-2:43 pm
Nonstop4h 21m
Boston Logan Intl
Wed 3/18
3:23 pm-7:19 pm
Nonstop3h 56m
$188
San JuanHartford
SJU - BDL
SJUBDL
San Juan Luis Munoz Marin Intl
Thu 4/23
11:59 pm-4:05 am
Nonstop4h 06m
Hartford Bradley Intl
Mon 4/27
8:08 pm-9:54 am
1 stop13h 46m
$202
San JuanHartford
SJU - BDL
SJUBDL
San Juan Luis Munoz Marin Intl
Thu 4/2
12:59 am-5:05 am
Nonstop4h 06m
Hartford Bradley Intl
Mon 4/6
6:00 am-9:53 am
Nonstop3h 53m
$221
OranjestadBoston
AUA - BOS
AUABOS
Oranjestad Reina Beatrix
Thu 3/26
3:20 pm-8:24 pm
Nonstop5h 04m
Boston Logan Intl
Fri 4/3
6:30 am-11:10 am
Nonstop4h 40m
$230
San JuanHartford
SJU - BDL
SJUBDL
San Juan Luis Munoz Marin Intl
Sun 4/5
3:16 am-1:53 pm
1 stop10h 37m
Hartford Bradley Intl
Sun 4/12
2:55 pm-12:52 am
1 stop9h 57m
$234
Saint Thomas IslandBoston
STT - BOS
STTBOS
Saint Thomas Island Cyril E King
Wed 3/25
2:41 pm-8:29 pm
1 stop5h 48m
Boston Logan Intl
Mon 3/30
9:00 am-1:04 pm
Nonstop4h 04m
$240
Saint Thomas IslandBoston
STT - BOS
STTBOS
Saint Thomas Island Cyril E King
Thu 3/26
2:45 pm-7:04 pm
Nonstop4h 19m
Boston Logan Intl
Sun 3/29
8:40 am-12:43 pm
Nonstop4h 03m
$241
Showing 1-10 of 60 results
Best time to book a flight from Caribbean to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Caribbean with our price prediction graph.
SJU-BOS
SJU-BDL
SDQ-BOS
STT-BOS
POS-BOS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Massachusetts
0CB-USMA
SJU-BOS
SJU-BDL
SDQ-BOS
STT-BOS
What is the cheapest month to book a flight from Caribbean to Massachusetts?
Currently, April is the cheapest month in which you can book a flight from Caribbean to Massachusetts (average of $63). Flying from Caribbean to Massachusetts in November is currently the most expensive (average of $141). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CB to MA?
Find hourly flight availability from Caribbean to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 13, 2026.
It’s typically best to fly out from Caribbean to Massachusetts at noon. Doing so could potentially save you 21% on the flight price compared to flying in the evening, which is usually more expensive.
What is the cheapest day to fly from Caribbean to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Caribbean to Massachusetts. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Caribbean to Massachusetts flight should consider departing on Thursday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Caribbean to Massachusetts
Explore weekly flight availability from Caribbean to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 13, 2026.
The most flights from 0CB to USMA are scheduled on a Friday (28 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 on average).
Reviews of airlines servicing Massachusetts
Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated February 13, 2026.
Read through reviews of airlines operating flights from Caribbean to Massachusetts, such as Delta, United Airlines, and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Caribbean to Massachusetts
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Massachusetts by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Massachusetts by cabin class
Find flights from Caribbean to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Massachusetts flights
Browse other Caribbean and Massachusetts flight options. Last updated on February 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Massachusetts
Find the right flight back to Caribbean after your stay in Massachusetts
Caribbean to Massachusetts flights
Consider these flights traveling from Caribbean to Massachusetts.
Top 7 airlines flying from Caribbean to Massachusetts
Discover the top 7 airlines that operate flights from Caribbean to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$75 | Average$289 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$86 | Average$286 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$110 | Average$410 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$136 | Average$459 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$169 | Average$389 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$208 | Average$455 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$449 | FlexibilityNo cancel fee | On-time71% |