$81+ Cheap flights from Boston (BOS) to Caribbean Islands
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 5/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
May 18 — May 251
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Caribbean Islands with Cheapflights
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Cheapest flights from Boston to Caribbean IslandsExplore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.
Explore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/56:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Wed 5/135:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/14![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/282:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Fri 5/155:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$175
This Frontier deal was found by Cheapflights users on 4/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:31 pm
BOS
- SJU
1 stop11h 12m
Frontier
Thu 5/145:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/13![Frontier logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Mon 5/1110:17 am
BOS
- SJU
1 stop7h 13m
Frontier
Fri 5/155:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/18![Frontier logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2310:40 am
BOS
- SJU
Nonstop3h 54m
Spirit Airlines
Wed 9/23:29 pm
SJU
- BOS
Nonstop4h 07m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$180
This Expedia deal was found by Cheapflights users on 4/17. 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.
Tue 8/2510:40 am
BOS
- SJU
Nonstop3h 54m
Spirit Airlines
Wed 9/23:29 pm
SJU
- BOS
Nonstop4h 07m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$181
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$184
This Priceline deal was found by Cheapflights users on 4/14. 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.
Sun 4/262:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Tue 5/58:30 am
SJU
- BOS
1 stop26h 36m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$185
This Super.com deal was found by Cheapflights users on 4/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:31 pm
BOS
- SJU
1 stop11h 12m
Frontier
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/14![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:06 am
BOS
- SJU
1 stop14h 55m
Frontier
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/13![Frontier logo]()
$188
This Booking.com deal was found by Cheapflights users on 4/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 4/262:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Thu 5/75:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$190
Best flights from Boston to Caribbean IslandsDiscover carefully curated flight deals from Boston to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 18, 2026.
Discover carefully curated flight deals from Boston to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 18, 2026.
This Delta deal was found by Cheapflights users on 4/15. 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.
Sun 5/35:35 am
BOS
- STT
1 stop9h 13m
Delta
Fri 5/154:27 pm
STT
- BOS
1 stop7h 10m
Delta
Deal found 4/15![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/25:45 am
BOS
- STT
1 stop6h 35m
United Airlines
Fri 5/82:10 pm
STT
- BOS
1 stop8h 04m
United Airlines
Deal found 4/15![United Airlines logo]()
$230
This American Airlines deal was found by Cheapflights users on 4/18. 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 6/46:00 am
BOS
- NAS
2 stops7h 17m
American Airlines
Mon 6/83:46 pm
NAS
- BOS
1 stop8h 03m
American Airlines
Deal found 4/18![American Airlines logo]()
$390
This Orbitz deal was found by Cheapflights users on 4/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:45 am
BOS
- MBJ
1 stop7h 46m
Multiple Airlines
Sun 6/712:30 pm
MBJ
- BOS
1 stop28h 29m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$398
This Travelocity deal was found by Cheapflights users on 4/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
BOS
- BGI
1 stop9h 25m
Air Canada
Sun 9/134:20 pm
BGI
- BOS
1 stop25h 44m
Air Canada
Deal found 4/14![Air Canada logo]()
$408
This JetBlue deal was found by Cheapflights users on 4/18. 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 4/2310:40 pm
BOS
- SJU
Nonstop3h 59m
JetBlue
Fri 5/223:30 am
SJU
- BOS
1 stop8h 06m
JetBlue
Deal found 4/18![JetBlue logo]()
$413
This Southwest deal was found by Cheapflights users on 4/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/610:15 pm
BOS
- SXM
2 stops15h 45m
Southwest
Fri 7/102:25 pm
SXM
- BOS
2 stops17h 40m
Southwest
Deal found 4/16![Southwest logo]()
$437
This Copa Airlines deal was found by Cheapflights users on 4/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/78:52 am
BOS
- AUA
1 stop13h 08m
Copa Airlines
Sun 6/147:10 am
AUA
- BOS
1 stop15h 58m
Copa Airlines
Deal found 4/17![Copa Airlines logo]()
$459
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:35 am
BOS
- STT
1 stop9h 13m
Delta
Tue 5/124:27 pm
STT
- BOS
1 stop7h 10m
Delta
Deal found 4/13![Delta logo]()
$230
This Arajet deal was found by Cheapflights users on 4/18. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:15 pm
BOS
- AUA
1 stop7h 15m
Arajet
Wed 9/308:15 pm
AUA
- BOS
2 stops24h 35m
Arajet
Deal found 4/18![Arajet logo]()
$466
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/128:00 am
BOS
- STT
1 stop7h 17m
Delta
Fri 5/154:27 pm
STT
- BOS
1 stop7h 10m
Delta
Deal found 4/13![Delta logo]()
$230
This United Airlines deal was found by Cheapflights users on 4/17. 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 6/27:27 pm
BOS
- SXM
1 stop17h 06m
United Airlines
Tue 6/93:50 pm
SXM
- BOS
1 stop8h 09m
United Airlines
Deal found 4/17![United Airlines logo]()
$310
This United Airlines deal was found by Cheapflights users on 4/13. 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.
Sat 5/95:45 am
BOS
- STT
2 stops11h 15m
United Airlines
Wed 5/204:45 pm
STT
- BOS
1 stop7h 14m
United Airlines
Deal found 4/13![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:35 am
BOS
- BGI
1 stop8h 45m
Delta
Mon 5/183:30 pm
BGI
- BOS
1 stop18h 16m
Delta
Deal found 4/16![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Mon 5/187:00 am
BOS
- SDQ
1 stop7h 10m
United Airlines
Fri 5/291:10 pm
SDQ
- BOS
1 stop8h 43m
United Airlines
Deal found 4/14![United Airlines logo]()
$322
This Orbitz deal was found by Cheapflights users on 4/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:12 am
BOS
- MBJ
Nonstop4h 22m
Multiple Airlines
Sat 6/2712:30 pm
MBJ
- BOS
1 stop9h 08m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$399
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:20 pm
BOS
- BGI
1 stop18h 00m
Delta
Mon 5/183:30 pm
BGI
- BOS
1 stop18h 16m
Delta
Deal found 4/16![Delta logo]()
$304
This American Airlines deal was found by Cheapflights users on 4/13. 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.
Sun 6/146:00 am
BOS
- STI
1 stop15h 13m
American Airlines
Sun 6/217:03 am
STI
- BOS
1 stop17h 56m
American Airlines
Deal found 4/13![American Airlines logo]()
$411
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/163:32 pm
BOS
- SDQ
1 stop7h 14m
United Airlines
Sat 5/236:00 am
SDQ
- BOS
1 stop7h 32m
United Airlines
Deal found 4/15![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:35 am
BOS
- BGI
1 stop8h 45m
Delta
Fri 5/83:30 pm
BGI
- BOS
1 stop9h 53m
Delta
Deal found 4/14![Delta logo]()
$304
This Air Canada deal was found by Cheapflights users on 4/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:40 pm
BOS
- MBJ
2 stops20h 40m
Air Canada
Sat 7/412:30 pm
MBJ
- BOS
2 stops20h 20m
Air Canada
Deal found 4/13![Air Canada logo]()
$450
This JetBlue deal was found by Cheapflights users on 4/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
BOS
- PUJ
Nonstop3h 57m
JetBlue
Wed 5/1312:30 pm
PUJ
- BOS
Nonstop4h 08m
JetBlue
Deal found 4/14![JetBlue logo]()
$455
This Copa Airlines deal was found by Cheapflights users on 4/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:47 am
BOS
- AUA
1 stop13h 12m
Copa Airlines
Sun 10/187:09 am
AUA
- BOS
1 stop15h 53m
Copa Airlines
Deal found 4/14![Copa Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Sat 5/235:45 am
BOS
- BGI
1 stop8h 05m
United Airlines
Sat 5/303:05 pm
BGI
- BOS
1 stop8h 54m
United Airlines
Deal found 4/15![United Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1110:15 pm
BOS
- SXM
2 stops15h 10m
Southwest
Mon 6/152:25 pm
SXM
- BOS
2 stops20h 30m
Southwest
Deal found 4/14![Southwest logo]()
$482
This JetBlue deal was found by Cheapflights users on 4/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/912:31 pm
BOS
- PUJ
Nonstop4h 08m
JetBlue
Sat 6/136:51 pm
PUJ
- BOS
Nonstop4h 08m
JetBlue
Deal found 4/16![JetBlue logo]()
$455
This Delta deal was found by Cheapflights users on 4/17. 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.
Sun 4/268:59 pm
BOS
- SXM
1 stop15h 11m
Delta
Thu 4/303:30 pm
SXM
- BOS
1 stop15h 59m
Delta
Deal found 4/17![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 4/18. 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 5/67:00 am
BOS
- SDQ
1 stop7h 10m
United Airlines
Tue 5/126:00 am
SDQ
- BOS
1 stop7h 51m
United Airlines
Deal found 4/18![United Airlines logo]()
$329
This Copa Airlines deal was found by Cheapflights users on 4/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:47 am
BOS
- AUA
1 stop13h 11m
Copa Airlines
Sun 9/207:10 am
AUA
- BOS
1 stop15h 52m
Copa Airlines
Deal found 4/14![Copa Airlines logo]()
$484
This Air Canada deal was found by Cheapflights users on 4/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/2610:50 am
BOS
- MBJ
1 stop25h 30m
Air Canada
Sun 8/912:30 pm
MBJ
- BOS
2 stops25h 11m
Air Canada
Deal found 4/13![Air Canada logo]()
$491
Last-minute flights from Boston to Caribbean IslandsDiscover last-minute flight deals from Boston to Caribbean Islands. Data last updated April 18, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated April 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 4/262:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Sat 5/95:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$180
This Priceline deal was found by Cheapflights users on 4/14. 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.
Sun 4/262:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Tue 5/58:30 am
SJU
- BOS
1 stop26h 36m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 4/262:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Thu 5/75:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$190
This Booking.com deal was found by Cheapflights users on 4/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/282:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Fri 5/155:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$175
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:06 am
BOS
- SJU
1 stop14h 55m
Frontier
Wed 5/65:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/13![Frontier logo]()
$188
This Frontier deal was found by Cheapflights users on 4/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:31 pm
BOS
- SJU
1 stop11h 12m
Frontier
Thu 5/145:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/13![Frontier logo]()
$176
This Priceline deal was found by Cheapflights users on 4/14. 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.
Mon 5/412:31 pm
BOS
- SJU
1 stop11h 12m
Frontier
Tue 5/125:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/14![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/56:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Wed 5/135:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/14![Frontier logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Wed 5/66:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Thu 5/145:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/14![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Mon 5/1110:17 am
BOS
- SJU
1 stop7h 13m
Frontier
Fri 5/155:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/18![Frontier logo]()
$178
One-way flights from Boston to Caribbean IslandsSearch for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
Search for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 18, 2026.
This Travelocity deal was found by Cheapflights users on 4/17. 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.
Sun 5/175:45 am
BOS
- SXM
1 stop7h 45m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$81
This United Airlines deal was found by Cheapflights users on 4/17. 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 6/35:45 am
BOS
- SXM
1 stop6h 48m
United Airlines
Deal found 4/17![United Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 4/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:25 am
BOS
- SJU
1 stop12h 59m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 4/13. 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.
Mon 4/275:55 am
BOS
- AUA
1 stop8h 41m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$95
This eDestinos deal was found by Cheapflights users on 4/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Deal found 4/16![Frontier logo]()
$96
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:20 pm
BOS
- BGI
1 stop18h 00m
Delta
Deal found 4/16![Delta logo]()
$96
This Super.com deal was found by Cheapflights users on 4/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/510:07 am
BOS
- SJU
1 stop16h 01m
Frontier
Deal found 4/15![Frontier logo]()
$97
This Priceline deal was found by Cheapflights users on 4/13. 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.
Tue 5/1910:07 am
BOS
- SJU
1 stop16h 01m
Frontier
Deal found 4/13![Frontier logo]()
$98
This American Airlines deal was found by Cheapflights users on 4/14. 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.
Wed 5/136:00 am
BOS
- SXM
2 stops9h 22m
American Airlines
Deal found 4/14![American Airlines logo]()
$99
This American Airlines deal was found by Cheapflights users on 4/17. 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 6/28:30 pm
BOS
- SXM
2 stops17h 20m
American Airlines
Deal found 4/17![American Airlines logo]()
$100
This eDestinos deal was found by Cheapflights users on 4/15. 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.
Sat 4/252:12 pm
BOS
- SJU
Nonstop3h 54m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$100
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Fri 5/17:26 pm
BOS
- SXM
2 stops17h 07m
United Airlines
Deal found 4/17![United Airlines logo]()
$101
Find flight deals from Boston to Caribbean Islands
Keep the following information in mind while searching for Boston to Caribbean Islands flight deals. Data was last updated April 18, 2026.
Round-trip from | $174 (Kiwi.com) |
|---|---|
One-way from | $81 (Travelocity) |
Popular in | December |
Cheapest in | January |
Average price | $336 |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Caribbean Islands 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 April 18, 2026.
Use the filters below to find and compare flights from Boston to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
Sun 5/3
5:35 am-2:48 pm
1 stop9h 13m
Saint Thomas Island Cyril E King
Fri 5/15
4:27 pm-11:37 pm
1 stop7h 10m
$230
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
Sat 5/2
5:45 am-12:20 pm
1 stop6h 35m
Saint Thomas Island Cyril E King
Fri 5/8
2:10 pm-10:14 pm
1 stop8h 04m
$230
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
Tue 5/5
5:35 am-2:48 pm
1 stop9h 13m
Saint Thomas Island Cyril E King
Tue 5/12
4:27 pm-11:37 pm
1 stop7h 10m
$230
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
Tue 5/12
8:00 am-3:17 pm
1 stop7h 17m
Saint Thomas Island Cyril E King
Fri 5/15
4:27 pm-11:37 pm
1 stop7h 10m
$230
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Tue 5/12
5:35 am-2:20 pm
1 stop8h 45m
Bridgetown Grantley Adams Intl
Mon 5/18
3:30 pm-9:46 am
1 stop18h 16m
$304
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Fri 5/15
8:20 pm-2:20 pm
1 stop18h 00m
Bridgetown Grantley Adams Intl
Mon 5/18
3:30 pm-9:46 am
1 stop18h 16m
$304
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Tue 5/5
5:35 am-2:20 pm
1 stop8h 45m
Bridgetown Grantley Adams Intl
Fri 5/8
3:30 pm-1:23 am
1 stop9h 53m
$304
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Tue 6/2
7:27 pm-12:33 pm
1 stop17h 06m
Simpson Bay Princess Juliana
Tue 6/9
3:50 pm-11:59 pm
1 stop8h 09m
$310
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Sun 4/26
8:59 pm-12:10 pm
1 stop15h 11m
Simpson Bay Princess Juliana
Thu 4/30
3:30 pm-7:29 am
1 stop15h 59m
$313
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
Sat 5/9
5:45 am-5:00 pm
2 stops11h 15m
Saint Thomas Island Cyril E King
Wed 5/20
4:45 pm-11:59 pm
1 stop7h 14m
$320
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Boston with our price prediction graph.
BOS-SJU
BOS-SXM
BOS-AUA
BOS-BGI
BOS-MBJ
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 Boston to Caribbean Islands
BOS-zzEPX
BOS-SJU
BOS-SXM
BOS-AUA
BOS-BGI
What is the cheapest month to book a flight from Boston to Caribbean Islands?
Currently, January is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $448). Flying from Boston to Caribbean Islands in December is currently the most expensive (average of $689). 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 BOS to EPX?
Find hourly flight availability from Boston to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 18, 2026.
A simple way to save on the total cost of your ticket is to fly from Boston to Caribbean Islands in the afternoon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Boston to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean Islands. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their Boston to Caribbean Islands flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Boston to Caribbean Islands
Explore weekly flight availability from Boston to Caribbean Islands. 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 April 18, 2026.
The most flights from BOS to zzEPX are scheduled on a Friday (16 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Caribbean Islands. Reviews last updated April 18, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andJetBlue from Boston to Caribbean Islands. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Boston to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Caribbean Islands by cabin class
Find flights from Boston to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Caribbean Islands flights
Browse other Boston and Caribbean Islands flight options. Last updated on April 18, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Boston to Caribbean Islands flights
Consider these flights traveling from Boston to Caribbean Islands.
Top 10 airlines flying from Boston to Caribbean Islands
Discover the top 10 airlines that operate flights from Boston to Caribbean Islands. 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 April 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$90 | Average$475 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$359 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$129 | Average$602 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$144 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$153 | Average$513 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$369 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$342 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$242 | Average$567 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$570 | FlexibilityNo cancel fee | On-time63% |