$107+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Jul 13 — Jul 201
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Boston to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Caribbean
Cheapest
Best
Last-minute
One-way
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 June 13, 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 June 13, 2026.
This SmartFares deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Wed 9/307:35 pm
SJU
- BOS
Nonstop4h 08m
JetBlue
Deal found 6/9![JetBlue logo]()
$298
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 7/142:53 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$306
This Faresmojo deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:50 pm
BOS
- SJU
Nonstop4h 04m
JetBlue
Mon 8/246:00 am
SJU
- BOS
1 stop9h 26m
JetBlue
Deal found 6/10![JetBlue logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Fri 9/257:35 pm
SJU
- BOS
Nonstop4h 08m
JetBlue
Deal found 6/9![JetBlue logo]()
$308
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/48:55 am
BOS
- STT
Nonstop4h 05m
JetBlue
Fri 7/102:49 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/8![JetBlue logo]()
$311
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/128:55 am
BOS
- SJU
Nonstop4h 06m
Delta
Sat 9/192:06 pm
SJU
- BOS
Nonstop4h 05m
Delta
Deal found 6/8![Delta logo]()
$313
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/910:30 am
BOS
- SJU
1 stop11h 53m
Delta
Fri 9/252:06 pm
SJU
- BOS
Nonstop4h 05m
Delta
Deal found 6/8![Delta logo]()
$318
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
BOS
- STT
2 stops9h 52m
American Airlines
Sat 8/292:20 pm
STT
- BOS
1 stop8h 30m
American Airlines
Deal found 6/10![American Airlines logo]()
$320
This Faresmojo deal was found by Cheapflights users on 6/13. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:59 am
BOS
- SJU
Nonstop4h 01m
JetBlue
Mon 8/245:01 am
SJU
- BOS
1 stop6h 20m
JetBlue
Deal found 6/13![JetBlue logo]()
$321
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2710:15 am
BOS
- SJU
Nonstop3h 58m
JetBlue
Tue 10/277:50 pm
SJU
- BOS
Nonstop4h 06m
JetBlue
Deal found 6/10![JetBlue logo]()
$323
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:22 pm
BOS
- STT
2 stops17h 31m
American Airlines
Wed 9/161:41 pm
STT
- BOS
2 stops18h 52m
American Airlines
Deal found 6/11![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:10 am
BOS
- SJU
2 stops12h 37m
American Airlines
Sat 9/122:58 pm
SJU
- BOS
2 stops8h 30m
American Airlines
Deal found 6/10![American Airlines logo]()
$327
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 June 13, 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 June 13, 2026.
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Mon 8/312:59 pm
SJU
- BOS
1 stop10h 26m
Delta
Deal found 6/9![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/142:15 pm
BOS
- SJU
1 stop8h 35m
Southwest
Tue 8/186:00 am
SJU
- BOS
1 stop8h 40m
Southwest
Deal found 6/10![Southwest logo]()
$342
This United Airlines deal was found by Cheapflights users on 6/12. 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 7/45:45 am
BOS
- SJU
1 stop6h 49m
United Airlines
Tue 7/71:00 am
SJU
- BOS
2 stops10h 52m
United Airlines
Deal found 6/12![United Airlines logo]()
$350
This JetBlue deal was found by Cheapflights users on 6/11. 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.
Sat 6/277:00 am
BOS
- BGI
Nonstop5h 02m
JetBlue
Sat 7/41:30 pm
BGI
- BOS
Nonstop5h 12m
JetBlue
Deal found 6/11![JetBlue logo]()
$398
This Copa Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/33:57 pm
BOS
- PUJ
1 stop19h 06m
Copa Airlines
Mon 7/611:46 am
PUJ
- BOS
1 stop11h 24m
Copa Airlines
Deal found 6/8![Copa Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/241:25 pm
BOS
- SJU
1 stop10h 19m
Delta
Mon 9/282:06 pm
SJU
- BOS
Nonstop4h 05m
Delta
Deal found 6/8![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 11/308:13 am
BOS
- SJU
Nonstop4h 07m
Delta
Mon 12/72:05 pm
SJU
- BOS
1 stop9h 21m
Delta
Deal found 6/11![Delta logo]()
$318
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/115:45 am
BOS
- SXM
1 stop6h 48m
United Airlines
Wed 7/153:50 pm
SXM
- BOS
1 stop8h 09m
United Airlines
Deal found 6/8![United Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 6/12. 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.
Thu 8/2012:40 pm
BOS
- SJU
2 stops10h 25m
Southwest
Wed 8/2611:50 am
SJU
- BOS
2 stops10h 20m
Southwest
Deal found 6/12![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:30 am
BOS
- SJU
1 stop7h 30m
Delta
Sat 10/242:06 pm
SJU
- BOS
Nonstop4h 05m
Delta
Deal found 6/10![Delta logo]()
$318
This Southwest deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:40 am
BOS
- SJU
2 stops9h 15m
Southwest
Mon 8/316:00 am
SJU
- BOS
2 stops8h 30m
Southwest
Deal found 6/10![Southwest logo]()
$362
This Delta deal was found by Cheapflights users on 6/11. 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 9/95:00 pm
BOS
- SJU
1 stop6h 59m
Delta
Wed 9/165:41 pm
SJU
- BOS
1 stop7h 36m
Delta
Deal found 6/11![Delta logo]()
$322
This JetBlue deal was found by Cheapflights users on 6/12. 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.
Sun 8/3011:05 am
BOS
- MBJ
Nonstop4h 19m
JetBlue
Wed 9/212:55 pm
MBJ
- BOS
1 stop10h 24m
JetBlue
Deal found 6/12![JetBlue logo]()
$432
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/76:00 am
BOS
- AUA
1 stop9h 35m
United Airlines
Tue 7/141:50 pm
AUA
- BOS
1 stop9h 31m
United Airlines
Deal found 6/12![United Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 6/12. 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 10/295:00 pm
BOS
- SJU
1 stop6h 56m
Delta
Mon 11/27:00 am
SJU
- BOS
1 stop7h 47m
Delta
Deal found 6/12![Delta logo]()
$322
This Copa Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/73:57 pm
BOS
- PUJ
1 stop10h 14m
Copa Airlines
Sun 7/121:32 pm
PUJ
- BOS
1 stop25h 02m
Copa Airlines
Deal found 6/9![Copa Airlines logo]()
$487
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:05 am
BOS
- SXM
1 stop8h 38m
United Airlines
Wed 8/53:50 pm
SXM
- BOS
2 stops18h 01m
United Airlines
Deal found 6/10![United Airlines logo]()
$404
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 11/1810:15 am
BOS
- STT
1 stop5h 29m
JetBlue
Sun 11/221:30 pm
STT
- BOS
1 stop7h 56m
JetBlue
Deal found 6/8![JetBlue logo]()
$460
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 11/89:00 pm
BOS
- SXM
2 stops17h 40m
Southwest
Fri 11/133:20 pm
SXM
- BOS
2 stops17h 50m
Southwest
Deal found 6/8![Southwest logo]()
$434
This United Airlines deal was found by Cheapflights users on 6/12. 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 9/76:00 am
BOS
- AUA
1 stop9h 20m
United Airlines
Fri 9/114:30 pm
AUA
- BOS
1 stop24h 18m
United Airlines
Deal found 6/12![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 6/11. 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.
Sun 8/305:30 am
BOS
- SXM
1 stop8h 23m
Delta
Wed 9/163:20 pm
SXM
- BOS
1 stop9h 57m
Delta
Deal found 6/11![Delta logo]()
$347
This Copa Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 8/123:57 pm
BOS
- PUJ
1 stop20h 52m
Copa Airlines
Sun 8/1611:46 am
PUJ
- BOS
1 stop11h 24m
Copa Airlines
Deal found 6/8![Copa Airlines logo]()
$512
This JetBlue deal was found by Cheapflights users on 6/12. 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.
Sat 7/117:00 am
BOS
- BGI
Nonstop5h 02m
JetBlue
Sat 7/183:05 pm
BGI
- BOS
1 stop8h 54m
JetBlue
Deal found 6/12![JetBlue logo]()
$513
This United Airlines deal was found by Cheapflights users on 6/12. 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 7/16:05 am
BOS
- PLS
2 stops10h 00m
United Airlines
Sat 7/252:35 pm
PLS
- BOS
1 stop8h 46m
United Airlines
Deal found 6/12![United Airlines logo]()
$428
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/55:30 am
BOS
- SXM
2 stops10h 00m
Southwest
Thu 7/92:25 pm
SXM
- BOS
2 stops17h 45m
Southwest
Deal found 6/8![Southwest logo]()
$474
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Tue 8/185:49 pm
SJU
- BOS
1 stop7h 36m
Delta
Deal found 6/9![Delta logo]()
$358
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/205:01 am
BOS
- BGI
1 stop11h 08m
JetBlue
Sat 7/251:30 pm
BGI
- BOS
Nonstop5h 11m
JetBlue
Deal found 6/9![JetBlue logo]()
$514
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/247:30 am
BOS
- PLS
2 stops8h 35m
United Airlines
Mon 6/295:15 pm
PLS
- BOS
2 stops16h 14m
United Airlines
Deal found 6/9![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 6/12. 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.
Tue 12/15:30 am
BOS
- SJU
1 stop7h 30m
Delta
Thu 12/244:35 pm
SJU
- BOS
Nonstop4h 26m
Delta
Deal found 6/12![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
BOS
- PLS
2 stops10h 05m
United Airlines
Wed 7/2912:35 pm
PLS
- BOS
2 stops11h 24m
United Airlines
Deal found 6/11![United Airlines logo]()
$433
Last-minute flights from Boston to CaribbeanDiscover last-minute flight deals from Boston to Caribbean. Data last updated June 13, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean. Data last updated June 13, 2026 and is based on user searches.
This SmartFares deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/209:44 pm
BOS
- SJU
Nonstop4h 00m
JetBlue
Fri 6/269:15 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 6/8![JetBlue logo]()
$338
This United Airlines deal was found by Cheapflights users on 6/12. 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 6/272:15 pm
BOS
- SJU
1 stop7h 09m
United Airlines
Tue 6/301:00 am
SJU
- BOS
1 stop7h 17m
United Airlines
Deal found 6/12![United Airlines logo]()
$322
This JetBlue deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/48:55 am
BOS
- STT
Nonstop4h 05m
JetBlue
Fri 7/102:49 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/8![JetBlue logo]()
$311
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:45 am
BOS
- SJU
1 stop6h 49m
United Airlines
Tue 7/71:00 am
SJU
- BOS
2 stops10h 52m
United Airlines
Deal found 6/11![United Airlines logo]()
$342
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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 7/43:19 pm
BOS
- SJU
1 stop9h 40m
JetBlue
Wed 7/86:30 am
SJU
- BOS
Nonstop4h 02m
JetBlue
Deal found 6/11![JetBlue logo]()
$347
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 7/142:53 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$306
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/125:45 am
BOS
- SJU
1 stop6h 49m
United Airlines
Thu 7/161:00 am
SJU
- BOS
1 stop7h 17m
United Airlines
Deal found 6/11![United Airlines logo]()
$327
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:35 pm
BOS
- SJU
1 stop11h 54m
United Airlines
Wed 7/221:00 am
SJU
- BOS
1 stop7h 17m
United Airlines
Deal found 6/11![United Airlines logo]()
$343
This JetBlue deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:55 am
BOS
- STT
Nonstop4h 04m
JetBlue
Tue 7/282:53 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/10![JetBlue logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/218:00 am
BOS
- SJU
1 stop13h 59m
American Airlines
Wed 8/510:33 am
SJU
- BOS
1 stop12h 53m
American Airlines
Deal found 6/12![American Airlines logo]()
$329
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:05 am
BOS
- SXM
1 stop8h 05m
Delta
Wed 7/293:20 pm
SXM
- BOS
1 stop10h 00m
Delta
Deal found 6/10![Delta logo]()
$347
This American Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:00 am
BOS
- SJU
1 stop13h 59m
American Airlines
Wed 8/57:24 pm
SJU
- BOS
1 stop14h 55m
American Airlines
Deal found 6/11![American Airlines logo]()
$332
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 June 13, 2026.
Search for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 13, 2026.
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:15 pm
BOS
- AUA
1 stop7h 15m
Arajet
Deal found 6/10![Arajet logo]()
$107
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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.
Wed 8/511:45 am
BOS
- PLS
Nonstop3h 55m
JetBlue
Deal found 6/8![JetBlue logo]()
$116
This Kissandfly.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:20 pm
BOS
- SXM
1 stop16h 54m
KLM
Deal found 6/10![KLM logo]()
$119
This United Airlines deal was found by Cheapflights users on 6/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:44 pm
BOS
- PLS
2 stops17h 55m
United Airlines
Deal found 6/11![United Airlines logo]()
$123
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:15 pm
BOS
- BGI
1 stop18h 05m
Delta
Deal found 6/10![Delta logo]()
$126
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 7/296:00 am
BOS
- PLS
2 stops8h 15m
American Airlines
Deal found 6/8![American Airlines logo]()
$128
This United Airlines deal was found by Cheapflights users on 6/12. 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.
Thu 7/98:15 pm
BOS
- PLS
2 stops18h 10m
United Airlines
Deal found 6/12![United Airlines logo]()
$129
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/75:30 am
BOS
- SXM
1 stop8h 23m
Delta
Deal found 6/8![Delta logo]()
$129
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:43 pm
BOS
- SXM
2 stops17h 50m
United Airlines
Deal found 6/10![United Airlines logo]()
$133
This Arajet deal was found by Cheapflights users on 6/12. 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 9/912:15 pm
BOS
- PUJ
1 stop7h 40m
Multiple Airlines
Deal found 6/12![Multiple Airlines logo]()
$134
This Super.com deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/57:15 am
BOS
- PLS
Nonstop3h 55m
JetBlue
Deal found 6/8![JetBlue logo]()
$135
This United Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:43 pm
BOS
- SXM
2 stops17h 50m
United Airlines
Deal found 6/10![United Airlines logo]()
$136
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 June 13, 2026.
Round-trip from | $298 (SmartFares) |
|---|---|
One-way from | $107 (Mytrip) |
Popular in | June |
Cheapest in | January |
Average price | $409 |
Good round-trip deal | $301 or less |
Good one-way deal | $158 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 June 13, 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
Thu 8/27
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Mon 8/31
2:59 pm-1:25 am
1 stop10h 26m
$318
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Thu 9/24
1:25 pm-11:44 pm
1 stop10h 19m
San Juan Luis Munoz Marin Intl
Mon 9/28
2:06 pm-6:11 pm
Nonstop4h 05m
$318
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
$318
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 10/17
5:30 am-1:00 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Sat 10/24
2:06 pm-6:11 pm
Nonstop4h 05m
$318
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Wed 9/9
5:00 pm-11:59 pm
1 stop6h 59m
San Juan Luis Munoz Marin Intl
Wed 9/16
5:41 pm-1:17 am
1 stop7h 36m
$322
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Thu 10/29
5:00 pm-11:56 pm
1 stop6h 56m
San Juan Luis Munoz Marin Intl
Mon 11/2
7:00 am-1:47 pm
1 stop7h 47m
$322
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Fri 8/14
2:15 pm-10:50 pm
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Tue 8/18
6:00 am-2:40 pm
1 stop8h 40m
$342
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Sun 8/30
5:30 am-1:53 pm
1 stop8h 23m
Simpson Bay Princess Juliana
Wed 9/16
3:20 pm-1:17 am
1 stop9h 57m
$347
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 7/4
5:45 am-12:34 pm
1 stop6h 49m
San Juan Luis Munoz Marin Intl
Tue 7/7
1:00 am-11:52 am
2 stops10h 52m
$350
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Sat 7/11
5:45 am-12:33 pm
1 stop6h 48m
Simpson Bay Princess Juliana
Wed 7/15
3:50 pm-11:59 pm
1 stop8h 09m
$355
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-PLS
BOS-BGI
BOS-PUJ
BOS-SJU
BOS-SXM
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-PLS
BOS-BGI
BOS-PUJ
BOS-SJU
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 $580). 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 June 13, 2026.
It’s typically best to fly out from Boston to Caribbean in the afternoon. Doing so could potentially save you 22% on the flight price compared to flying at noon, which is usually more expensive.
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 June 13, 2026.
Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Sunday at noon 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 June 13, 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.
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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.
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
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 June 13, 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 June 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$442 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$504 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$147 | Average$466 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$517 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$463 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$397 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$242 | Average$575 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$569 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$317 | Average$537 | FlexibilityNo cancel fee | On-timeN/A |