$125+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Aug 20 — Aug 271
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 Islands 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 Islands
Cheapest
Best
Last-minute
One-way
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 July 21, 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 July 21, 2026.
This SmartFares deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/87:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Mon 10/126:12 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 7/21![JetBlue logo]()
$300
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/197:05 am
BOS
- SJU
2 stops13h 33m
United Airlines
Mon 9/211:00 am
SJU
- BOS
2 stops9h 18m
United Airlines
Deal found 7/21![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/118:55 am
BOS
- SJU
Nonstop4h 06m
Delta
Mon 10/121:06 pm
SJU
- BOS
1 stop10h 02m
Delta
Deal found 7/21![Delta logo]()
$302
This Cheapflightsfares deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/277:25 pm
BOS
- SJU
Nonstop4h 00m
JetBlue
Wed 11/118:45 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 7/21![JetBlue logo]()
$303
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/107:42 am
BOS
- SJU
1 stop7h 58m
American Airlines
Fri 9/112:58 pm
SJU
- BOS
1 stop6h 55m
American Airlines
Deal found 7/21![American Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:15 am
BOS
- SJU
1 stop8h 21m
Multiple Airlines
Fri 10/305:12 pm
SJU
- BOS
1 stop16h 17m
Multiple Airlines
Deal found 7/21![Multiple Airlines logo]()
$308
This Cheapflightsfares deal was found by Cheapflights users on 7/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Sun 10/116:12 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 7/18![JetBlue logo]()
$309
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/225:45 am
BOS
- SJU
1 stop6h 49m
United Airlines
Mon 10/267:25 am
SJU
- BOS
1 stop10h 08m
United Airlines
Deal found 7/20![United Airlines logo]()
$310
This Booking.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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
- CUR
2 stops8h 50m
Arajet
Sun 10/412:35 pm
CUR
- BOS
1 stop8h 15m
Arajet
Deal found 7/20![Arajet logo]()
$310
This American Airlines deal was found by Cheapflights users on 7/18. 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.
Mon 8/317:34 pm
BOS
- STT
2 stops17h 19m
American Airlines
Wed 9/21:49 pm
STT
- BOS
2 stops18h 57m
American Airlines
Deal found 7/18![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 10/298:55 am
BOS
- SJU
Nonstop4h 06m
Delta
Mon 11/22:06 pm
SJU
- BOS
1 stop9h 20m
Delta
Deal found 7/21![Delta logo]()
$311
This American Airlines deal was found by Cheapflights users on 7/17. 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.
Wed 10/286:00 am
BOS
- SJU
1 stop7h 19m
American Airlines
Wed 10/283:51 pm
SJU
- BOS
1 stop7h 08m
American Airlines
Deal found 7/17![American Airlines logo]()
$312
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 July 21, 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 July 21, 2026.
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/186:00 am
BOS
- SJU
1 stop7h 45m
United Airlines
Sat 9/191:00 am
SJU
- BOS
2 stops9h 18m
United Airlines
Deal found 7/21![United Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 7/18. 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 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
Sun 9/62:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 7/18![Delta logo]()
$335
This JetBlue deal was found by Cheapflights users on 7/18. 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.
Sat 9/126:55 am
BOS
- SJU
1 stop6h 39m
JetBlue
Fri 9/186:00 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 7/18![JetBlue logo]()
$349
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 10/152:35 pm
BOS
- SJU
2 stops9h 45m
Southwest
Thu 10/225:30 am
SJU
- BOS
1 stop10h 35m
Southwest
Deal found 7/19![Southwest logo]()
$354
This Arajet deal was found by Cheapflights users on 7/18. 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.
Fri 9/1812:15 pm
BOS
- SDQ
Nonstop4h 15m
Arajet
Sun 10/44:35 pm
SDQ
- BOS
Nonstop4h 15m
Arajet
Deal found 7/18![Arajet logo]()
$385
This Copa Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/233:55 pm
BOS
- CUR
1 stop20h 23m
Copa Airlines
Sun 9/277:31 pm
CUR
- BOS
1 stop27h 31m
Copa Airlines
Deal found 7/21![Copa Airlines logo]()
$454
This WorldTicket deal was found by Cheapflights users on 7/17. 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 WorldTicket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1811:15 am
BOS
- SDQ
Nonstop4h 15m
WorldTicket
Fri 1/86:30 am
SDQ
- BOS
Nonstop4h 15m
WorldTicket
Deal found 7/17![WorldTicket logo]()
$455
This Avianca deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:50 pm
BOS
- CUR
2 stops17h 30m
Avianca
Wed 9/26:15 pm
CUR
- BOS
1 stop12h 55m
Avianca
Deal found 7/19![Avianca logo]()
$495
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/248:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Mon 8/312:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 7/20![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/227:05 am
BOS
- SJU
2 stops13h 33m
United Airlines
Sat 8/294:55 pm
SJU
- BOS
1 stop7h 04m
United Airlines
Deal found 7/21![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/212:15 pm
BOS
- SJU
1 stop8h 35m
Southwest
Wed 8/268:20 am
SJU
- BOS
2 stops10h 15m
Southwest
Deal found 7/21![Southwest logo]()
$358
This Delta deal was found by Cheapflights users on 7/18. 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 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
Thu 9/31:19 pm
SJU
- BOS
1 stop9h 24m
Delta
Deal found 7/18![Delta logo]()
$340
This JetBlue deal was found by Cheapflights users on 7/17. 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 JetBlue 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
Sat 9/511:36 am
NAS
- BOS
Nonstop3h 24m
JetBlue
Deal found 7/17![JetBlue logo]()
$393
This Southwest deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/202:15 pm
BOS
- SJU
1 stop8h 35m
Southwest
Thu 8/275:00 am
SJU
- BOS
2 stops9h 30m
Southwest
Deal found 7/20![Southwest logo]()
$364
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/228:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Sat 8/292:31 pm
SJU
- BOS
1 stop9h 28m
Delta
Deal found 7/21![Delta logo]()
$340
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/56:00 am
BOS
- SXM
1 stop6h 33m
United Airlines
Sat 9/121:35 pm
SXM
- BOS
2 stops20h 43m
United Airlines
Deal found 7/19![United Airlines logo]()
$382
This WorldTicket deal was found by Cheapflights users on 7/17. 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 WorldTicket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/209:20 pm
BOS
- SDQ
Nonstop4h 15m
WorldTicket
Sun 1/34:35 pm
SDQ
- BOS
Nonstop4h 15m
WorldTicket
Deal found 7/17![WorldTicket logo]()
$455
This Delta deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/12:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 7/19![Delta logo]()
$349
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/38:50 am
BOS
- STT
Nonstop4h 25m
JetBlue
Mon 10/53:40 pm
STT
- BOS
1 stop8h 03m
JetBlue
Deal found 7/20![JetBlue logo]()
$425
This Copa Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 9/103:55 pm
BOS
- CUR
1 stop26h 36m
Copa Airlines
Wed 9/167:31 pm
CUR
- BOS
1 stop19h 08m
Copa Airlines
Deal found 7/20![Copa Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 12/86:00 am
BOS
- SXM
1 stop6h 50m
United Airlines
Tue 12/152:52 pm
SXM
- BOS
2 stops24h 31m
United Airlines
Deal found 7/20![United Airlines logo]()
$388
This Arajet deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 7/19![Arajet logo]()
$505
This Copa Airlines deal was found by Cheapflights users on 7/18. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/243:55 pm
BOS
- AUA
1 stop20h 14m
Copa Airlines
Thu 10/17:09 am
AUA
- BOS
1 stop15h 53m
Copa Airlines
Deal found 7/18![Copa Airlines logo]()
$470
This Delta deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/288:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Tue 9/17:30 am
SJU
- BOS
1 stop8h 43m
Delta
Deal found 7/20![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Sat 11/78:05 pm
BOS
- SXM
1 stop16h 45m
United Airlines
Sat 11/212:10 pm
SXM
- BOS
1 stop10h 12m
United Airlines
Deal found 7/17![United Airlines logo]()
$418
This JetBlue deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 10/38:50 am
BOS
- STT
Nonstop4h 25m
JetBlue
Wed 10/144:54 pm
STT
- BOS
1 stop6h 49m
JetBlue
Deal found 7/20![JetBlue logo]()
$465
This Arajet deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 7/20![Arajet logo]()
$515
This Copa Airlines deal was found by Cheapflights users on 7/17. 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.
Mon 11/92:50 pm
BOS
- CUR
1 stop26h 32m
Copa Airlines
Sun 11/157:21 pm
CUR
- BOS
1 stop27h 40m
Copa Airlines
Deal found 7/17![Copa Airlines logo]()
$472
This Avianca deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:45 am
BOS
- CUR
1 stop25h 35m
Avianca
Wed 9/166:15 pm
CUR
- BOS
2 stops44h 35m
Avianca
Deal found 7/20![Avianca logo]()
$572
This Southwest deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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.
Sat 8/225:50 am
BOS
- MBJ
1 stop7h 35m
Southwest
Sat 8/2911:40 am
MBJ
- BOS
1 stop9h 00m
Southwest
Deal found 7/19![Southwest logo]()
$497
Last-minute flights from Boston to Caribbean IslandsDiscover last-minute flight deals from Boston to Caribbean Islands. Data last updated July 21, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated July 21, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/117:50 pm
BOS
- SJU
Nonstop4h 04m
JetBlue
Thu 8/135:45 am
SJU
- BOS
Nonstop4h 00m
JetBlue
Deal found 7/20![JetBlue logo]()
$330
This Frontier deal was found by Cheapflights users on 7/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:04 am
BOS
- SJU
1 stop7h 27m
Frontier
Tue 8/118:37 pm
SJU
- BOS
1 stop12h 32m
Frontier
Deal found 7/18![Frontier logo]()
$331
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/157:50 pm
BOS
- SJU
Nonstop4h 04m
JetBlue
Wed 8/198:54 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 7/20![JetBlue logo]()
$327
This Super.com deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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
Fri 8/282:49 pm
STT
- BOS
Nonstop5h 43m
JetBlue
Deal found 7/20![JetBlue logo]()
$317
This SmartFares deal was found by Cheapflights users on 7/18. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/229:10 am
BOS
- SJU
Nonstop4h 01m
JetBlue
Wed 9/28:07 pm
SJU
- BOS
Nonstop4h 06m
JetBlue
Deal found 7/18![JetBlue logo]()
$320
This JetBlue deal was found by Cheapflights users on 7/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2410:10 am
BOS
- SJU
Nonstop4h 01m
JetBlue
Thu 8/275:45 am
SJU
- BOS
Nonstop4h 00m
JetBlue
Deal found 7/17![JetBlue logo]()
$335
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 Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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
Sun 9/132:10 pm
SJU
- BOS
Nonstop4h 13m
Delta
Deal found 7/21![Delta logo]()
$316
This Cheapflightsfares deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 8/277:50 pm
BOS
- SJU
Nonstop4h 04m
JetBlue
Thu 9/35:14 am
SJU
- BOS
Nonstop4h 00m
JetBlue
Deal found 7/19![JetBlue logo]()
$332
This United Airlines deal was found by Cheapflights users on 7/17. 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 8/286:00 am
BOS
- SJU
1 stop7h 45m
United Airlines
Tue 9/81:00 am
SJU
- BOS
1 stop8h 48m
United Airlines
Deal found 7/17![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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.
Sat 8/2911:09 am
BOS
- SJU
1 stop7h 21m
American Airlines
Tue 9/87:03 am
SJU
- BOS
1 stop15h 47m
American Airlines
Deal found 7/19![American Airlines logo]()
$325
This American Airlines deal was found by Cheapflights users on 7/18. 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.
Mon 8/317:34 pm
BOS
- STT
2 stops17h 19m
American Airlines
Wed 9/21:49 pm
STT
- BOS
2 stops18h 57m
American Airlines
Deal found 7/18![American Airlines logo]()
$310
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 July 21, 2026.
Search for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated July 21, 2026.
This Air Canada deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 7/19![Air Canada logo]()
$125
This Air Canada deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 11/155:30 am
BOS
- NAS
1 stop7h 45m
Air Canada
Deal found 7/19![Air Canada logo]()
$131
This Expedia deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/1810:50 am
BOS
- NAS
1 stop6h 40m
Air Canada
Deal found 7/19![Air Canada logo]()
$136
This Trip.com deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:50 pm
BOS
- NAS
1 stop18h 45m
Air Canada
Deal found 7/19![Air Canada logo]()
$142
This Delta deal was found by Cheapflights users on 7/17. 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 1/38:45 pm
BOS
- SXM
1 stop14h 30m
Delta
Deal found 7/17![Delta logo]()
$144
This Expedia deal was found by Cheapflights users on 7/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:40 am
BOS
- NAS
1 stop26h 55m
Air Canada
Deal found 7/18![Air Canada logo]()
$144
This Travelocity deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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.
Tue 10/202:45 pm
BOS
- NAS
2 stops22h 50m
Air Canada
Deal found 7/21![Air Canada logo]()
$145
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 9/186:50 pm
BOS
- SXM
2 stops17h 43m
United Airlines
Deal found 7/19![United Airlines logo]()
$147
This United Airlines deal was found by Cheapflights users on 7/19. Clicking the “Pick Dates” 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 12/126:00 am
BOS
- SXM
1 stop8h 57m
United Airlines
Deal found 7/19![United Airlines logo]()
$148
This Orbitz deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:45 am
BOS
- NAS
1 stop7h 50m
Air Canada
Deal found 7/20![Air Canada logo]()
$148
This United Airlines deal was found by Cheapflights users on 7/20. Clicking the “Pick Dates” 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 8/37:27 pm
BOS
- SXM
1 stop17h 06m
United Airlines
Deal found 7/20![United Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/208:20 pm
BOS
- SXM
2 stops17h 45m
Southwest
Deal found 7/21![Southwest logo]()
$150
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 July 21, 2026.
Round-trip from | $307 (American Airlines) |
|---|---|
One-way from | $125 (Air Canada) |
Popular in | July |
Cheapest in | January |
Average price | $447 |
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 July 21, 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
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Fri 9/18
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Sat 9/19
1:00 am-10:18 am
2 stops9h 18m
$315
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Wed 9/2
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Sun 9/6
2:10 pm-6:21 pm
Nonstop4h 11m
$335
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Mon 8/24
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
$335
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
Thu 9/3
1:19 pm-10:43 pm
1 stop9h 24m
$340
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 8/22
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Sat 8/29
2:31 pm-11:59 pm
1 stop9h 28m
$340
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 8/22
7:05 am-8:38 pm
2 stops13h 33m
San Juan Luis Munoz Marin Intl
Sat 8/29
4:55 pm-11:59 pm
1 stop7h 04m
$344
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 9/12
6:55 am-1:34 pm
1 stop6h 39m
San Juan Luis Munoz Marin Intl
Fri 9/18
6:00 am-10:03 am
Nonstop4h 03m
$349
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 8/29
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Tue 9/1
2:10 pm-6:21 pm
Nonstop4h 11m
$349
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Thu 10/15
2:35 pm-12:20 am
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Thu 10/22
5:30 am-4:05 pm
1 stop10h 35m
$354
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Fri 8/28
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Tue 9/1
7:30 am-4:13 pm
1 stop8h 43m
$354
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-SXM
BOS-NAS
BOS-STT
BOS-PUJ
BOS-CUR
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-SXM
BOS-NAS
BOS-STT
BOS-PUJ
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 $467). Flying from Boston to Caribbean Islands in December is currently the most expensive (average of $674). 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 July 21, 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 23% on your trip compared to booking a flight at noon.
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 July 21, 2026.
The most flights from BOS to zzEPX are scheduled on a Monday (11 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 Islands?
The price you pay for your flight from Boston to Caribbean Islands may vary depending on when you book. For the best chance of a lower fare, look to book 36 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 July 18, 2026.
Travelers seeking maximum savings on their Boston to Caribbean Islands 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 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 July 21, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines 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
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Crew
8.5
Overall
7.8
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 Islands. 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 destinations
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 July 21, 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 July 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$456 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$569 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$148 | Average$463 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$164 | Average$519 | 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$397 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$242 | Average$581 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$570 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$317 | Average$576 | FlexibilityNo cancel fee | On-timeN/A |