$110+ Cheap flights from Boston (BOS) to Caribbean
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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Aug 15 — Aug 221
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Caribbean with Cheapflights
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Cheapest flights from Boston to CaribbeanExplore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
Explore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2026.
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 9/82:58 pm
STT
- BOS
1 stop5h 39m
JetBlue
Deal found 7/15![JetBlue logo]()
$301
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Fri 8/282:49 pm
STT
- BOS
1 stop5h 43m
JetBlue
Deal found 7/15![JetBlue logo]()
$302
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Sun 9/206:00 am
BOS
- SJU
2 stops9h 07m
American Airlines
Mon 9/286:00 am
SJU
- BOS
1 stop17h 29m
American Airlines
Deal found 7/12![American Airlines logo]()
$306
This Priceline deal was found by Cheapflights users on 7/12. 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.
Wed 10/1411:05 am
BOS
- SJU
1 stop9h 39m
Multiple Airlines
Sun 10/186:12 am
SJU
- BOS
Nonstop4h 03m
Multiple Airlines
Deal found 7/12![Multiple Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 7/12. 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.
Mon 9/216:00 am
BOS
- SJU
2 stops8h 50m
American Airlines
Thu 9/242:58 pm
SJU
- BOS
1 stop10h 01m
American Airlines
Deal found 7/12![American Airlines logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Tue 10/2710:15 am
BOS
- SJU
Nonstop3h 58m
JetBlue
Tue 10/277:50 pm
SJU
- BOS
Nonstop4h 06m
JetBlue
Deal found 7/13![JetBlue logo]()
$309
This Delta deal was found by Cheapflights users on 7/13. 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.
Wed 9/28:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Tue 9/82:10 pm
SJU
- BOS
Nonstop4h 13m
Delta
Deal found 7/13![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 7/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:30 am
BOS
- STT
1 stop8h 13m
United Airlines
Sat 9/52:10 pm
STT
- BOS
2 stops9h 49m
United Airlines
Deal found 7/16![United Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Wed 9/96:00 am
BOS
- SJU
2 stops9h 40m
American Airlines
Sat 9/126:00 am
SJU
- BOS
1 stop17h 57m
American Airlines
Deal found 7/13![American Airlines logo]()
$311
This JetBlue deal was found by Cheapflights users on 7/12. 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.
Mon 9/217:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Tue 9/226:00 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 7/12![JetBlue logo]()
$312
This Super.com deal was found by Cheapflights users on 7/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Mon 10/196:12 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 7/16![JetBlue logo]()
$313
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:20 am
BOS
- SJU
Nonstop4h 09m
JetBlue
Sun 10/186:12 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 7/15![JetBlue logo]()
$314
Best flights from Boston to CaribbeanDiscover carefully curated flight deals from Boston to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
Discover carefully curated flight deals from Boston to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 16, 2026.
This Delta deal was found by Cheapflights users on 7/14. 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.
Wed 10/288:55 am
BOS
- SJU
Nonstop4h 06m
Delta
Sun 11/17:00 am
SJU
- BOS
1 stop7h 47m
Delta
Deal found 7/14![Delta logo]()
$315
This JetBlue deal was found by Cheapflights users on 7/14. 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.
Wed 8/512:50 pm
BOS
- SJU
Nonstop4h 01m
JetBlue
Wed 8/128:54 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 7/14![JetBlue logo]()
$343
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Mon 11/167:37 pm
BOS
- SXM
2 stops17h 13m
United Airlines
Sat 11/212:10 pm
SXM
- BOS
1 stop10h 12m
United Airlines
Deal found 7/12![United Airlines logo]()
$365
This Air Canada deal was found by Cheapflights users on 7/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2410:35 am
BOS
- NAS
1 stop26h 40m
Air Canada
Sun 11/292:05 pm
NAS
- BOS
1 stop7h 23m
Air Canada
Deal found 7/11![Air Canada logo]()
$378
This Southwest deal was found by Cheapflights users on 7/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:55 am
BOS
- SJU
2 stops11h 10m
Southwest
Fri 9/2510:00 am
SJU
- BOS
2 stops9h 40m
Southwest
Deal found 7/13![Southwest logo]()
$383
This Copa Airlines deal was found by Cheapflights users on 7/12. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:55 pm
BOS
- AUA
1 stop22h 49m
Copa Airlines
Sun 10/181:19 pm
AUA
- BOS
1 stop9h 43m
Copa Airlines
Deal found 7/12![Copa Airlines logo]()
$470
This Arajet deal was found by Cheapflights users on 7/12. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1612:15 pm
BOS
- AUA
1 stop7h 15m
Arajet
Sun 9/2011:00 am
AUA
- BOS
2 stops9h 50m
Arajet
Deal found 7/12![Arajet logo]()
$505
This Delta deal was found by Cheapflights users on 7/13. 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.
Sat 9/59:05 am
BOS
- SJU
1 stop7h 28m
Delta
Wed 9/92:10 pm
SJU
- BOS
Nonstop4h 13m
Delta
Deal found 7/13![Delta logo]()
$315
This Arajet deal was found by Cheapflights users on 7/16. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3010:20 pm
BOS
- PUJ
1 stop12h 30m
Multiple Airlines
Sun 8/211:50 am
PUJ
- BOS
1 stop9h 00m
Multiple Airlines
Deal found 7/16![Multiple Airlines logo]()
$649
This Delta deal was found by Cheapflights users on 7/14. 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.
Mon 10/268:55 am
BOS
- SJU
Nonstop4h 06m
Delta
Mon 11/22:06 pm
SJU
- BOS
1 stop9h 20m
Delta
Deal found 7/14![Delta logo]()
$315
This JetBlue deal was found by Cheapflights users on 7/11. 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.
Mon 8/246:00 am
BOS
- STT
1 stop8h 55m
JetBlue
Tue 9/11:53 pm
STT
- BOS
1 stop5h 46m
JetBlue
Deal found 7/11![JetBlue logo]()
$368
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Sat 12/56:00 am
BOS
- SXM
1 stop6h 50m
United Airlines
Thu 12/102:52 pm
SXM
- BOS
2 stops22h 55m
United Airlines
Deal found 7/12![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 7/16. 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.
Thu 10/293:34 pm
BOS
- SJU
1 stop8h 22m
Delta
Mon 11/27:00 am
SJU
- BOS
1 stop7h 47m
Delta
Deal found 7/16![Delta logo]()
$315
This Air Canada deal was found by Cheapflights users on 7/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:10 pm
BOS
- NAS
2 stops22h 05m
Air Canada
Mon 11/302:05 pm
NAS
- BOS
1 stop7h 23m
Air Canada
Deal found 7/11![Air Canada logo]()
$386
This JetBlue deal was found by Cheapflights users on 7/11. 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.
Fri 8/216:00 am
BOS
- STT
1 stop9h 09m
JetBlue
Tue 9/11:53 pm
STT
- BOS
1 stop5h 46m
JetBlue
Deal found 7/11![JetBlue logo]()
$368
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Mon 8/318:30 pm
BOS
- PLS
1 stop15h 09m
United Airlines
Thu 9/312:45 pm
PLS
- BOS
1 stop9h 14m
United Airlines
Deal found 7/15![United Airlines logo]()
$375
This Delta deal was found by Cheapflights users on 7/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Mon 8/312:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 7/11![Delta logo]()
$323
This Air Canada deal was found by Cheapflights users on 7/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:50 pm
BOS
- NAS
2 stops22h 40m
Air Canada
Sat 10/176:30 pm
NAS
- BOS
2 stops20h 11m
Air Canada
Deal found 7/11![Air Canada logo]()
$394
This JetBlue deal was found by Cheapflights users on 7/11. 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.
Fri 8/216:00 am
BOS
- STT
1 stop9h 09m
JetBlue
Fri 8/282:49 pm
STT
- BOS
1 stop5h 43m
JetBlue
Deal found 7/11![JetBlue logo]()
$368
This United Airlines deal was found by Cheapflights users on 7/15. 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.
Mon 10/197:38 am
BOS
- SJU
1 stop6h 07m
United Airlines
Tue 10/201:00 am
SJU
- BOS
2 stops9h 32m
United Airlines
Deal found 7/15![United Airlines logo]()
$376
This Copa Airlines deal was found by Cheapflights users on 7/11. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/123:55 pm
BOS
- AUA
1 stop20h 15m
Copa Airlines
Mon 10/197:09 am
AUA
- BOS
1 stop15h 53m
Copa Airlines
Deal found 7/11![Copa Airlines logo]()
$473
This Delta deal was found by Cheapflights users on 7/12. 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.
Mon 11/308:13 am
BOS
- SJU
Nonstop4h 07m
Delta
Mon 12/72:05 pm
SJU
- BOS
1 stop9h 21m
Delta
Deal found 7/12![Delta logo]()
$328
This JetBlue deal was found by Cheapflights users on 7/11. 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.
Mon 8/246:00 am
BOS
- STT
1 stop8h 55m
JetBlue
Tue 8/251:53 pm
STT
- BOS
1 stop5h 45m
JetBlue
Deal found 7/11![JetBlue logo]()
$382
This United Airlines deal was found by Cheapflights users on 7/13. 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 9/237:30 am
BOS
- NAS
1 stop6h 03m
United Airlines
Mon 9/282:53 pm
NAS
- BOS
2 stops18h 40m
United Airlines
Deal found 7/13![United Airlines logo]()
$390
This JetBlue deal was found by Cheapflights users on 7/11. 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.
Sun 8/236:00 am
BOS
- STT
1 stop8h 55m
JetBlue
Tue 8/251:53 pm
STT
- BOS
1 stop5h 45m
JetBlue
Deal found 7/11![JetBlue logo]()
$386
This Southwest deal was found by Cheapflights users on 7/12. 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.
Tue 8/185:25 am
BOS
- MBJ
1 stop8h 30m
Southwest
Fri 8/212:15 pm
MBJ
- BOS
2 stops16h 45m
Southwest
Deal found 7/12![Southwest logo]()
$568
This Delta deal was found by Cheapflights users on 7/16. 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.
Sat 11/143:34 pm
BOS
- SJU
1 stop7h 21m
Delta
Sun 11/227:15 am
SJU
- BOS
1 stop9h 07m
Delta
Deal found 7/16![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 7/13. 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 7/306:00 am
BOS
- NAS
1 stop8h 57m
United Airlines
Mon 8/32:53 pm
NAS
- BOS
1 stop8h 37m
United Airlines
Deal found 7/13![United Airlines logo]()
$401
This Copa Airlines deal was found by Cheapflights users on 7/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:47 am
BOS
- AUA
1 stop9h 50m
Copa Airlines
Tue 10/133:46 pm
AUA
- BOS
1 stop22h 53m
Copa Airlines
Deal found 7/15![Copa Airlines logo]()
$534
This Southwest deal was found by Cheapflights users on 7/12. 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.
Sun 8/307:20 am
BOS
- MBJ
1 stop8h 05m
Southwest
Sun 9/62:00 pm
MBJ
- BOS
2 stops18h 00m
Southwest
Deal found 7/12![Southwest logo]()
$570
Last-minute flights from Boston to CaribbeanDiscover last-minute flight deals from Boston to Caribbean. Data last updated July 16, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean. Data last updated July 16, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 7/12. 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.
Wed 7/2910:04 am
BOS
- SJU
1 stop24h 39m
Frontier
Wed 8/196:09 pm
SJU
- BOS
1 stop15h 00m
Frontier
Deal found 7/12![Frontier logo]()
$322
This JetBlue deal was found by Cheapflights users on 7/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Fri 8/282:49 pm
STT
- BOS
1 stop5h 43m
JetBlue
Deal found 7/15![JetBlue logo]()
$302
This Super.com deal was found by Cheapflights users on 7/15. 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.
Fri 8/219:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 8/251:53 pm
STT
- BOS
Nonstop5h 45m
JetBlue
Deal found 7/15![JetBlue logo]()
$318
This Cheapflightsfares deal was found by Cheapflights users on 7/13. 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.
Sun 8/236:00 am
BOS
- SJU
Nonstop4h 00m
JetBlue
Wed 9/25:15 am
SJU
- BOS
Nonstop4h 00m
JetBlue
Deal found 7/13![JetBlue logo]()
$320
This Justfly.com deal was found by Cheapflights users on 7/15. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Sat 8/292:00 pm
STT
- BOS
1 stop5h 39m
JetBlue
Deal found 7/15![JetBlue logo]()
$301
This Super.com deal was found by Cheapflights users on 7/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/259:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 9/11:53 pm
STT
- BOS
Nonstop5h 46m
JetBlue
Deal found 7/16![JetBlue logo]()
$321
This United Airlines deal was found by Cheapflights users on 7/14. 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.
Wed 8/267:30 am
BOS
- SJU
2 stops13h 08m
United Airlines
Wed 9/93:56 pm
SJU
- BOS
1 stop9h 14m
United Airlines
Deal found 7/14![United Airlines logo]()
$319
This JetBlue deal was found by Cheapflights users on 7/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
BOS
- SJU
Nonstop4h 00m
JetBlue
Wed 9/26:11 pm
SJU
- BOS
Nonstop4h 07m
JetBlue
Deal found 7/13![JetBlue logo]()
$323
This American Airlines deal was found by Cheapflights users on 7/12. 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 8/285:27 am
BOS
- STT
1 stop9h 32m
American Airlines
Thu 9/34:42 pm
STT
- BOS
1 stop8h 16m
American Airlines
Deal found 7/12![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 7/13. 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.
Sat 8/298:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Tue 9/82:10 pm
SJU
- BOS
Nonstop4h 13m
Delta
Deal found 7/13![Delta logo]()
$310
This United Airlines deal was found by Cheapflights users on 7/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:45 am
BOS
- STT
1 stop7h 13m
United Airlines
Sat 9/54:45 pm
STT
- BOS
1 stop7h 14m
United Airlines
Deal found 7/16![United Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 7/13. 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.
Mon 8/316:26 pm
BOS
- STT
2 stops18h 27m
American Airlines
Mon 9/281:41 pm
STT
- BOS
2 stops18h 52m
American Airlines
Deal found 7/13![American Airlines logo]()
$326
One-way flights from Boston to CaribbeanSearch for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
Search for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 16, 2026.
This Booking.com deal was found by Cheapflights users on 7/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:15 pm
BOS
- AUA
1 stop7h 15m
Arajet
Deal found 7/11![Arajet logo]()
$110
This Kissandfly.com deal was found by Cheapflights users on 7/12. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:56 pm
BOS
- SXM
1 stop16h 57m
KLM
Deal found 7/12![KLM logo]()
$125
This Air Canada deal was found by Cheapflights users on 7/13. 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 8/2910:40 am
BOS
- NAS
1 stop26h 55m
Air Canada
Deal found 7/13![Air Canada logo]()
$132
This Delta deal was found by Cheapflights users on 7/12. 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.
Fri 8/148:45 pm
BOS
- SXM
1 stop17h 08m
Delta
Deal found 7/12![Delta logo]()
$134
This Expedia deal was found by Cheapflights users on 7/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/910:50 am
BOS
- NAS
1 stop6h 40m
Air Canada
Deal found 7/16![Air Canada logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 7/11. 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.
Sat 8/297:15 am
BOS
- PLS
Nonstop3h 55m
JetBlue
Deal found 7/11![JetBlue logo]()
$137
This United Airlines deal was found by Cheapflights users on 7/13. 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 9/126:00 am
BOS
- SXM
1 stop6h 33m
United Airlines
Deal found 7/13![United Airlines logo]()
$138
This Flightnetwork deal was found by Cheapflights users on 7/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2710:50 am
BOS
- NAS
1 stop6h 40m
Air Canada
Deal found 7/16![Air Canada logo]()
$138
This Air Canada deal was found by Cheapflights users on 7/12. 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 8/275:45 am
BOS
- NAS
2 stops11h 45m
Air Canada
Deal found 7/12![Air Canada logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 7/12. 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 8/297:00 am
BOS
- NAS
Nonstop3h 35m
JetBlue
Deal found 7/12![JetBlue logo]()
$143
This Delta deal was found by Cheapflights users on 7/13. 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.
Sun 1/38:45 pm
BOS
- SXM
1 stop14h 30m
Delta
Deal found 7/13![Delta logo]()
$144
This Expedia deal was found by Cheapflights users on 7/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:40 am
BOS
- NAS
1 stop26h 55m
Air Canada
Deal found 7/16![Air Canada logo]()
$145
Find flight deals from Boston to Caribbean
Keep the following information in mind while searching for Boston to Caribbean flight deals. Data was last updated July 16, 2026.
Round-trip from | $301 (JetBlue) |
|---|---|
One-way from | $110 (Booking.com) |
Popular in | July |
Cheapest in | January |
Average price | $438 |
Good round-trip deal | $321 or less |
Good one-way deal | $168 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Caribbean 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 July 16, 2026.
Use the filters below to find and compare flights from Boston to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Wed 10/28
8:55 am-1:01 pm
Nonstop4h 06m
San Juan Luis Munoz Marin Intl
Sun 11/1
7:00 am-1:47 pm
1 stop7h 47m
$315
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 9/5
9:05 am-4:33 pm
1 stop7h 28m
San Juan Luis Munoz Marin Intl
Wed 9/9
2:10 pm-6:23 pm
Nonstop4h 13m
$315
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Mon 10/26
8:55 am-1:01 pm
Nonstop4h 06m
San Juan Luis Munoz Marin Intl
Mon 11/2
2:06 pm-10:26 pm
1 stop9h 20m
$315
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Thu 10/29
3:34 pm-11:56 pm
1 stop8h 22m
San Juan Luis Munoz Marin Intl
Mon 11/2
7:00 am-1:47 pm
1 stop7h 47m
$315
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Wed 8/26
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Mon 8/31
2:10 pm-6:21 pm
Nonstop4h 11m
$323
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Mon 11/30
8:13 am-1:20 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Mon 12/7
2:05 pm-10:26 pm
1 stop9h 21m
$328
Quickest round-trip
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Wed 8/5
12:50 pm-4:51 pm
Nonstop4h 01m
San Juan Luis Munoz Marin Intl
Wed 8/12
8:54 pm-12:59 am
Nonstop4h 05m
$343
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 11/14
3:34 pm-11:55 pm
1 stop7h 21m
San Juan Luis Munoz Marin Intl
Sun 11/22
7:15 am-3:22 pm
1 stop9h 07m
$358
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Mon 11/16
7:37 pm-1:50 pm
2 stops17h 13m
Simpson Bay Princess Juliana
Sat 11/21
2:10 pm-11:22 pm
1 stop10h 12m
$365
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
Mon 8/24
6:00 am-2:55 pm
1 stop8h 55m
Saint Thomas Island Cyril E King
Tue 9/1
1:53 pm-7:39 pm
1 stop5h 46m
$368
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Boston with our price prediction graph.
BOS-SJU
BOS-SXM
BOS-NAS
BOS-AUA
BOS-PUJ
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
BOS-0CB
BOS-SJU
BOS-SXM
BOS-NAS
BOS-AUA
What is the cheapest month to book a flight from Boston to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Boston to Caribbean (average of $403). Flying from Boston to Caribbean in December is currently the most expensive (average of $579). 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 CB?
Find hourly flight availability from Boston to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 16, 2026.
It’s typically best to fly out from Boston to Caribbean in the afternoon. Doing so could potentially save you 23% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Boston to Caribbean
Explore weekly flight availability from Boston to Caribbean. 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 July 16, 2026.
The most flights from BOS to 0CB are scheduled on a Thursday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Boston to Caribbean?
The best time to book flights from Boston to Caribbean is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Boston to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean. Price data was last updated on July 11, 2026.
Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Wednesday evenings 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.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated July 16, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Boston to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Comfort
7.8
Food
7.2
Boarding
8.1
Entertainment
7.8
Overall
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean. 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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Caribbean by cabin class
Find flights from Boston to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Caribbean flights
Browse other Boston and Caribbean flight options. Last updated on July 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Boston to Caribbean flights
Consider these flights traveling from Boston to Caribbean.
Top 10 airlines flying from Boston to Caribbean
Discover the top 10 airlines that operate flights from Boston to Caribbean. 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 July 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$434 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$583 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$147 | Average$462 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$161 | Average$518 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$460 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$345 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$183 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$242 | Average$583 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$570 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$317 | Average$537 | FlexibilityNo cancel fee | On-timeN/A |