$94+ Cheap flights from Caribbean Islands 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — BOS
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Caribbean Islands to Massachusetts with Cheapflights
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Cheapest flights from Caribbean Islands to MassachusettsExplore the most affordable flight options available from Caribbean Islands to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
Explore the most affordable flight options available from Caribbean Islands to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 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.
Thu 2/263:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 2/276:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Mon 3/28:01 pm
BOS
- SJU
Nonstop4h 07m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$124
This Expedia deal was found by Cheapflights users on 2/15. 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.
Thu 3/511:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Wed 3/118:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$133
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Tue 3/38:01 pm
BOS
- SJU
Nonstop4h 07m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$135
This Priceline deal was found by Cheapflights users on 2/14. 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.
Fri 2/276:00 am
SJU
- BOS
Nonstop4h 19m
Frontier
Mon 3/210:04 am
BOS
- SJU
Nonstop3h 56m
Frontier
Deal found 2/14![Frontier logo]()
$136
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- BOS
1 stop13h 07m
Spirit Airlines
Tue 3/38:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$140
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 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 2/193:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Thu 2/266:00 pm
BDL
- SJU
1 stop7h 53m
Frontier
Deal found 2/12![Frontier logo]()
$168
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Wed 2/183:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Tue 2/247:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/15![Frontier logo]()
$171
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Thu 2/263:53 am
SJU
- BDL
1 stop6h 55m
Frontier
Sun 3/17:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/15![Frontier logo]()
$172
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.
Wed 5/63:19 pm
SJU
- BDL
1 stop27h 58m
Frontier
Fri 5/158:08 pm
BDL
- SJU
1 stop19h 29m
Frontier
Deal found 2/13![Frontier logo]()
$174
Best flights from Caribbean Islands to MassachusettsDiscover carefully curated flight deals from Caribbean Islands to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
Discover carefully curated flight deals from Caribbean Islands to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
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 eDestinos deal was found by Cheapflights users on 2/15. 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.
Thu 2/263:53 am
SJU
- BDL
1 stop6h 55m
Frontier
Sun 3/17:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/15![Frontier logo]()
$172
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:22 am
SJU
- BOS
Nonstop4h 21m
Multiple Airlines
Mon 2/2310:04 am
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$174
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 2/15. 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.
Tue 3/102:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Tue 3/178:40 am
BOS
- STT
Nonstop4h 03m
Delta
Deal found 2/15![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 2/14. 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
1 stop7h 35m
American Airlines
Deal found 2/14![American Airlines logo]()
$250
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:35 am
SJU
- BDL
1 stop10h 35m
Southwest
Tue 5/512:50 pm
BDL
- SJU
1 stop9h 50m
Southwest
Deal found 2/12![Southwest logo]()
$262
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/34:35 pm
SDQ
- BOS
Nonstop4h 15m
Arajet
Sun 5/3110:20 pm
BOS
- SDQ
Nonstop4h 15m
Arajet
Deal found 2/12![Arajet logo]()
$311
This Spirit deal was found by Cheapflights users on 2/15. 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 4/1010:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Tue 4/143:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$171
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2610:35 pm
PUJ
- BOS
1 stop18h 22m
Air Canada
Sun 3/226:40 pm
BOS
- PUJ
1 stop22h 50m
Air Canada
Deal found 2/12![Air Canada logo]()
$383
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:08 am
SJU
- BOS
1 stop7h 13m
Frontier
Sun 5/106:00 am
BOS
- SJU
1 stop8h 08m
Frontier
Deal found 2/12![Frontier logo]()
$192
This Spirit deal was found by Cheapflights users on 2/15. 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 2/253:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$175
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:16 pm
SJU
- BOS
1 stop9h 57m
Multiple Airlines
Mon 3/24:22 pm
BOS
- SJU
1 stop16h 55m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$195
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 3/2610:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Mon 3/306:01 am
BOS
- SJU
1 stop17h 57m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$183
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Wed 3/412:43 pm
BOS
- SJU
1 stop9h 26m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$206
This Frontier 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 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 2/12![Frontier logo]()
$207
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.
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 2/14. 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.
Tue 3/311:50 pm
AUA
- BOS
2 stops34h 09m
United Airlines
Tue 4/71:30 pm
BOS
- AUA
2 stops25h 50m
United Airlines
Deal found 2/14![United Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 2/15. 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 3/56:00 am
SJU
- BDL
1 stop15h 13m
American Airlines
Tue 3/1011:33 am
BDL
- SJU
2 stops11h 25m
American Airlines
Deal found 2/15![American Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 2/15. 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 4/221:00 am
SJU
- ALB
2 stops14h 12m
United Airlines
Sat 4/2511:30 am
ALB
- SJU
1 stop9h 04m
United Airlines
Deal found 2/15![United Airlines logo]()
$242
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.
Mon 3/211:22 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]()
$201
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 Southwest deal was found by Cheapflights users on 2/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/154:25 pm
SJU
- ALB
1 stop6h 50m
Southwest
Mon 5/182:55 pm
ALB
- SJU
1 stop8h 45m
Southwest
Deal found 2/15![Southwest logo]()
$280
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Thu 5/146:30 am
SJU
- BDL
1 stop12h 47m
Frontier
Tue 6/26:15 am
BDL
- SJU
Nonstop4h 06m
Frontier
Deal found 2/15![Frontier logo]()
$233
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 3/263:55 pm
STT
- BOS
1 stop6h 59m
Delta
Mon 3/306:00 am
BOS
- STT
1 stop7h 00m
Delta
Deal found 2/12![Delta logo]()
$250
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 3/56:01 am
SJU
- BDL
Nonstop4h 04m
JetBlue
Mon 3/97:49 pm
BDL
- SJU
Nonstop3h 51m
JetBlue
Deal found 2/12![JetBlue logo]()
$276
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
This Southwest deal was found by Cheapflights users on 2/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:45 pm
SJU
- ALB
1 stop6h 35m
Southwest
Sat 4/255:05 pm
ALB
- SJU
1 stop6h 10m
Southwest
Deal found 2/15![Southwest logo]()
$280
Last-minute flights from Caribbean Islands to MassachusettsDiscover last-minute flight deals from Caribbean Islands to Massachusetts. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean Islands to Massachusetts. Data last updated February 16, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Wed 2/183:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Tue 2/247:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/15![Frontier logo]()
$171
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 2/193:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Thu 2/266:00 pm
BDL
- SJU
1 stop7h 53m
Frontier
Deal found 2/12![Frontier logo]()
$168
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 2/263:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Sun 3/13:00 pm
BOS
- SJU
Nonstop4h 06m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$122
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- BOS
1 stop13h 07m
Spirit Airlines
Tue 3/38:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$140
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 eDestinos deal was found by Cheapflights users on 2/15. 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.
Thu 2/263:53 am
SJU
- BDL
1 stop6h 55m
Frontier
Sun 3/17:55 pm
BDL
- SJU
Nonstop3h 51m
Frontier
Deal found 2/15![Frontier logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 2/276:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Mon 3/28:01 pm
BOS
- SJU
Nonstop4h 07m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$124
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
SJU
- BOS
Nonstop4h 19m
Multiple Airlines
Tue 3/38:01 pm
BOS
- SJU
Nonstop4h 07m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$135
This Priceline deal was found by Cheapflights users on 2/14. 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.
Fri 2/276:00 am
SJU
- BOS
Nonstop4h 19m
Frontier
Mon 3/210:04 am
BOS
- SJU
Nonstop3h 56m
Frontier
Deal found 2/14![Frontier logo]()
$136
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 Expedia deal was found by Cheapflights users on 2/15. 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.
Thu 3/511:22 am
SJU
- BOS
Nonstop4h 21m
Spirit Airlines
Wed 3/118:01 pm
BOS
- SJU
Nonstop4h 07m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$133
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.
Thu 3/53:55 pm
SJU
- BDL
Nonstop4h 15m
Frontier
Mon 3/98:08 pm
BDL
- SJU
1 stop14h 04m
Frontier
Deal found 2/13![Frontier logo]()
$175
One-way flights from Caribbean Islands to MassachusettsSearch for one-way flight options from Caribbean Islands to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
Search for one-way flight options from Caribbean Islands to Massachusetts. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- BOS
1 stop13h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$94
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
SJU
- BOS
Nonstop4h 16m
Frontier
Deal found 2/12![Frontier logo]()
$95
This CheapOair deal was found by Cheapflights users on 2/16. 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.
Wed 5/63:08 am
SJU
- BOS
1 stop7h 13m
Frontier
Deal found 2/16![Frontier logo]()
$96
This Expedia deal was found by Cheapflights users on 2/14. 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 2/253:30 pm
SJU
- BOS
Nonstop4h 26m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/1110:52 am
SJU
- BOS
1 stop13h 07m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 2/14![Spirit Airlines logo]()
$101
This CheapOair deal was found by Cheapflights users on 2/16. 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.
Wed 4/86:30 am
SJU
- BOS
1 stop28h 01m
Frontier
Deal found 2/16![Frontier 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.
Sun 5/103:08 am
SJU
- BOS
1 stop7h 13m
Frontier
Deal found 2/12![Frontier logo]()
$104
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:27 pm
SJU
- BOS
2 stops30h 17m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$105
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:00 am
SJU
- BOS
Nonstop4h 16m
Frontier
Deal found 2/12![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 2/14. 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 4/2810:53 am
SJU
- BOS
1 stop29h 35m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$109
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.
Tue 4/214:40 pm
STT
- BOS
1 stop7h 19m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$111
Find flight deals from Caribbean Islands to Massachusetts
Keep the following information in mind while searching for Caribbean Islands to Massachusetts flight deals. Data was last updated February 16, 2026.
Round-trip from | $122 (Cheapflightsfares) |
|---|---|
One-way from | $94 (eDestinos) |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean Islands 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 16, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Massachusetts that are best for you.
Fly from
Caribbean Islands
Fly to
Massachusetts
Route
Depart
Return
Price
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 JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Fri 4/10
10:00 am-2:18 pm
Nonstop4h 18m
Boston Logan Intl
Tue 4/14
3:23 pm-7:19 pm
Nonstop3h 56m
$171
San JuanHartford
SJU - BDL
SJUBDL
San Juan Luis Munoz Marin Intl
Thu 2/26
3:53 am-9:48 am
1 stop6h 55m
Hartford Bradley Intl
Sun 3/1
7:55 pm-12:46 am
Nonstop3h 51m
$172
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Thu 2/19
11:22 am-2:43 pm
Nonstop4h 21m
Boston Logan Intl
Mon 2/23
10:04 am-3:00 pm
Nonstop3h 56m
$174
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Wed 2/25
3:30 pm-6:56 pm
Nonstop4h 26m
Boston Logan Intl
Sun 3/1
3:00 pm-8:06 pm
Nonstop4h 06m
$175
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Thu 3/26
10:00 am-2:18 pm
Nonstop4h 18m
Boston Logan Intl
Mon 3/30
6:01 am-11:58 pm
1 stop17h 57m
$183
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Wed 5/6
3:08 am-10:21 am
1 stop7h 13m
Boston Logan Intl
Sun 5/10
6:00 am-2:08 pm
1 stop8h 08m
$192
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Fri 2/27
4:16 pm-1:13 am
1 stop9h 57m
Boston Logan Intl
Mon 3/2
4:22 pm-10:17 am
1 stop16h 55m
$195
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Mon 3/2
11:22 am-2:43 pm
Nonstop4h 21m
Boston Logan Intl
Sun 3/8
8:01 pm-12:08 am
Nonstop4h 07m
$201
San JuanBoston
SJU - BOS
SJUBOS
San Juan Luis Munoz Marin Intl
Sat 2/28
6:00 am-9:19 am
Nonstop4h 19m
Boston Logan Intl
Wed 3/4
12:43 pm-11:09 pm
1 stop9h 26m
$206
Showing 1-10 of 60 results
Best time to book a flight from Caribbean Islands to Massachusetts
Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Caribbean Islands with our price prediction graph.
SJU-BDL
SJU-ALB
SJU-BOS
STT-BOS
SDQ-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 Islands to Massachusetts
zzEPX-USMA
SJU-BDL
SJU-ALB
SJU-BOS
STT-BOS
What is the cheapest month to book a flight from Caribbean Islands to Massachusetts?
Currently, April is the cheapest month in which you can book a flight from Caribbean Islands to Massachusetts (average of $64). Flying from Caribbean Islands 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 EPX to MA?
Find hourly flight availability from Caribbean Islands 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 16, 2026.
It’s typically best to fly out from Caribbean Islands 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 Islands to Massachusetts?
Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Massachusetts. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Caribbean Islands 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 Islands to Massachusetts
Explore weekly flight availability from Caribbean Islands 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 16, 2026.
The most flights from zzEPX to USMA are scheduled on a Friday (30 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (23 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 16, 2026.
See what other customers who have flown with Delta, United Airlines, and American Airlines from Caribbean Islands to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Overall
7.9
Food
7.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Food
7.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Food
7.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Food
7.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Food
7.2
Boarding
8.1
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Overall
7.9
Food
7.2
Boarding
8.1
Comfort
7.9
Crew
8.5
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 Islands 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 Islands 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 Islands to Massachusetts by cabin class
Find flights from Caribbean Islands to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean Islands and Massachusetts flights
Browse other Caribbean Islands and Massachusetts flight options. Last updated on February 16, 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 Islands after your stay in Massachusetts
Caribbean Islands to Massachusetts flights
Consider these flights traveling from Caribbean Islands to Massachusetts.
Top 7 airlines flying from Caribbean Islands to Massachusetts
Discover the top 7 airlines that operate flights from Caribbean Islands 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 16, 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% |