$94+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
May 29 — Jun 51
Round-trip
1 adult, Economy
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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
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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 April 29, 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 April 29, 2026.
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:07 am
BOS
- SJU
1 stop12h 36m
Frontier
Wed 5/205:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/26![Frontier logo]()
$192
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sat 5/910:07 am
BOS
- SJU
1 stop12h 36m
Frontier
Sat 5/165:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/25![Frontier logo]()
$194
This Priceline deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Wed 5/135:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/26![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Sat 5/165:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/28![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/126:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Tue 5/195:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/27![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Fri 5/155:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/28![Frontier logo]()
$210
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:07 am
BOS
- SJU
1 stop21h 57m
Frontier
Tue 5/128:30 am
SJU
- BOS
1 stop26h 36m
Frontier
Deal found 4/26![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:07 am
BOS
- SJU
1 stop7h 07m
Frontier
Wed 5/205:15 pm
SJU
- BOS
1 stop14h 34m
Frontier
Deal found 4/28![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Fri 6/55:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/28![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/272:12 pm
BOS
- SJU
Nonstop3h 54m
Multiple Airlines
Wed 5/205:15 pm
SJU
- BOS
1 stop8h 09m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sat 5/306:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Sun 6/79:00 am
SJU
- BOS
1 stop26h 06m
Frontier
Deal found 4/28![Frontier logo]()
$219
This Trip.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Thu 5/1410:07 am
BOS
- SJU
1 stop12h 36m
Frontier
Tue 5/196:00 am
SJU
- BOS
1 stop27h 12m
Frontier
Deal found 4/25![Frontier logo]()
$220
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 April 29, 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 April 29, 2026.
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/306:00 am
BOS
- SXM
1 stop8h 06m
Delta
Sat 6/63:45 pm
SXM
- BOS
1 stop15h 39m
Delta
Deal found 4/27![Delta logo]()
$297
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/67:30 am
BOS
- BGI
1 stop7h 55m
United Airlines
Sat 6/133:05 pm
BGI
- BOS
1 stop8h 54m
United Airlines
Deal found 4/24![United Airlines logo]()
$304
This JetBlue deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:59 pm
BOS
- SJU
Nonstop4h 02m
JetBlue
Tue 5/127:11 pm
SJU
- BOS
Nonstop4h 09m
JetBlue
Deal found 4/25![JetBlue logo]()
$363
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/175:30 am
BOS
- SXM
1 stop7h 10m
Southwest
Wed 5/202:25 pm
SXM
- BOS
2 stops17h 40m
Southwest
Deal found 4/26![Southwest logo]()
$411
This Orbitz deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 5/175:45 am
BOS
- SDQ
1 stop9h 21m
Multiple Airlines
Sun 5/245:01 am
SDQ
- BOS
Nonstop4h 08m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$438
This Arajet deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2212:15 pm
BOS
- SDQ
Nonstop4h 15m
Arajet
Sun 6/144:35 pm
SDQ
- BOS
Nonstop4h 15m
Arajet
Deal found 4/27![Arajet logo]()
$446
This Copa Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/244:00 pm
BOS
- SDQ
1 stop18h 55m
Copa Airlines
Sun 5/316:04 am
SDQ
- BOS
1 stop17h 04m
Copa Airlines
Deal found 4/25![Copa Airlines logo]()
$486
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/275:35 am
BOS
- BGI
1 stop8h 45m
Delta
Tue 6/23:40 pm
BGI
- BOS
1 stop9h 48m
Delta
Deal found 4/28![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:45 am
BOS
- BGI
1 stop8h 05m
United Airlines
Sat 5/304:35 pm
BGI
- BOS
1 stop16h 37m
United Airlines
Deal found 4/24![United Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/295:35 am
BOS
- BGI
1 stop8h 45m
Delta
Tue 6/23:40 pm
BGI
- BOS
1 stop9h 48m
Delta
Deal found 4/28![Delta logo]()
$304
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:00 am
BOS
- BGI
1 stop9h 25m
United Airlines
Sat 5/164:35 pm
BGI
- BOS
1 stop15h 18m
United Airlines
Deal found 4/25![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 8/245:45 am
BOS
- SXM
1 stop8h 11m
Delta
Fri 8/283:21 pm
SXM
- BOS
1 stop9h 45m
Delta
Deal found 4/25![Delta logo]()
$305
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/155:45 am
BOS
- SXM
1 stop6h 48m
United Airlines
Thu 7/233:50 pm
SXM
- BOS
2 stops16h 27m
United Airlines
Deal found 4/28![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 7/215:30 am
BOS
- SJU
1 stop7h 41m
Delta
Tue 7/285:56 pm
SJU
- BOS
1 stop7h 24m
Delta
Deal found 4/25![Delta logo]()
$312
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2610:08 am
BOS
- SDQ
1 stop14h 14m
JetBlue
Mon 6/13:10 am
SDQ
- BOS
Nonstop3h 59m
JetBlue
Deal found 4/28![JetBlue logo]()
$441
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/96:00 am
BOS
- SXM
1 stop8h 06m
Delta
Sat 5/163:35 pm
SXM
- BOS
1 stop15h 47m
Delta
Deal found 4/26![Delta logo]()
$314
This Orbitz deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Fri 9/257:40 pm
BOS
- PUJ
2 stops20h 25m
Multiple Airlines
Sat 10/34:40 pm
PUJ
- BOS
Nonstop4h 12m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$460
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/136:00 am
BOS
- BGI
1 stop9h 25m
United Airlines
Sat 7/44:35 pm
BGI
- BOS
1 stop17h 16m
United Airlines
Deal found 4/28![United Airlines logo]()
$348
This Copa Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/163:57 pm
BOS
- SDQ
1 stop18h 58m
Copa Airlines
Fri 7/2412:43 pm
SDQ
- BOS
1 stop10h 27m
Copa Airlines
Deal found 4/27![Copa Airlines logo]()
$486
This JetBlue deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/116:00 am
BOS
- PUJ
1 stop11h 12m
JetBlue
Thu 5/144:02 pm
PUJ
- BOS
Nonstop4h 15m
JetBlue
Deal found 4/25![JetBlue logo]()
$456
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/95:45 am
BOS
- SXM
1 stop6h 48m
United Airlines
Sat 6/133:50 pm
SXM
- BOS
2 stops17h 49m
United Airlines
Deal found 4/27![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/158:50 am
BOS
- SJU
Nonstop4h 03m
Delta
Thu 7/232:03 pm
SJU
- BOS
Nonstop4h 07m
Delta
Deal found 4/26![Delta logo]()
$333
This JetBlue deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/268:30 pm
BOS
- AUA
1 stop14h 40m
JetBlue
Sat 5/3012:20 pm
AUA
- BOS
Nonstop4h 53m
JetBlue
Deal found 4/28![JetBlue logo]()
$464
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/66:00 am
BOS
- SJU
1 stop10h 29m
Delta
Sun 6/142:05 pm
SJU
- BOS
Nonstop4h 09m
Delta
Deal found 4/24![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/178:30 am
BOS
- SDQ
1 stop14h 16m
United Airlines
Thu 5/216:00 am
SDQ
- BOS
1 stop9h 16m
United Airlines
Deal found 4/28![United Airlines logo]()
$378
This JetBlue deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 9/218:55 pm
BOS
- STI
Nonstop4h 26m
JetBlue
Thu 9/246:30 am
STI
- BOS
Nonstop3h 55m
JetBlue
Deal found 4/27![JetBlue logo]()
$473
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/29:05 am
BOS
- SJU
1 stop7h 24m
Delta
Tue 6/92:05 pm
SJU
- BOS
Nonstop4h 09m
Delta
Deal found 4/27![Delta logo]()
$338
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/17:25 am
BOS
- NAS
1 stop8h 31m
United Airlines
Mon 7/63:59 pm
NAS
- BOS
1 stop9h 09m
United Airlines
Deal found 4/28![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/286:05 am
BOS
- SJU
1 stop10h 33m
Delta
Fri 7/312:03 pm
SJU
- BOS
Nonstop4h 07m
Delta
Deal found 4/28![Delta logo]()
$348
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:00 am
BOS
- NAS
1 stop5h 28m
United Airlines
Tue 6/212:35 pm
NAS
- BOS
1 stop6h 53m
United Airlines
Deal found 4/26![United Airlines logo]()
$386
Last-minute flights from Boston to CaribbeanDiscover last-minute flight deals from Boston to Caribbean. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean. Data last updated April 29, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:07 am
BOS
- SJU
1 stop21h 57m
Frontier
Tue 5/128:30 am
SJU
- BOS
1 stop26h 36m
Frontier
Deal found 4/26![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sat 5/910:07 am
BOS
- SJU
1 stop12h 36m
Frontier
Sat 5/165:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/25![Frontier logo]()
$194
This Priceline deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Wed 5/135:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/26![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:17 am
BOS
- SJU
1 stop7h 13m
Frontier
Mon 5/186:00 am
SJU
- BOS
1 stop27h 12m
Frontier
Deal found 4/24![Frontier logo]()
$215
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/126:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Tue 5/195:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/27![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Fri 5/155:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/28![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Sat 5/165:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/28![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:07 am
BOS
- SJU
1 stop7h 07m
Frontier
Wed 5/205:15 pm
SJU
- BOS
1 stop14h 34m
Frontier
Deal found 4/28![Frontier logo]()
$212
This Trip.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Thu 5/1410:07 am
BOS
- SJU
1 stop12h 36m
Frontier
Tue 5/196:00 am
SJU
- BOS
1 stop27h 12m
Frontier
Deal found 4/25![Frontier logo]()
$220
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:07 am
BOS
- SJU
1 stop12h 36m
Frontier
Wed 5/205:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/26![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2010:07 am
BOS
- SJU
1 stop16h 01m
Frontier
Fri 5/295:15 pm
SJU
- BOS
1 stop8h 09m
Frontier
Deal found 4/28![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sat 5/306:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Sun 6/79:00 am
SJU
- BOS
1 stop26h 06m
Frontier
Deal found 4/28![Frontier logo]()
$219
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 April 29, 2026.
Search for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
- SXM
1 stop9h 42m
American Airlines
Deal found 4/28![American Airlines logo]()
$94
This eDestinos deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1410:07 am
BOS
- SJU
1 stop7h 07m
Frontier
Deal found 4/24![Frontier logo]()
$96
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:35 am
BOS
- BGI
1 stop8h 45m
Delta
Deal found 4/28![Delta logo]()
$96
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/126:00 am
BOS
- SJU
1 stop8h 07m
Frontier
Deal found 4/27![Frontier logo]()
$98
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/36:00 am
BOS
- SXM
1 stop6h 40m
American Airlines
Deal found 4/28![American Airlines logo]()
$99
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:26 pm
BOS
- SXM
2 stops16h 07m
United Airlines
Deal found 4/28![United Airlines logo]()
$100
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:26 pm
BOS
- SXM
2 stops17h 07m
United Airlines
Deal found 4/28![United Airlines logo]()
$101
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:00 am
BOS
- BGI
2 stops14h 36m
American Airlines
Deal found 4/27![American Airlines logo]()
$101
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/105:35 am
BOS
- BGI
1 stop8h 45m
Delta
Deal found 4/24![Delta logo]()
$103
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/1910:07 am
BOS
- SJU
1 stop7h 03m
Frontier
Deal found 4/26![Frontier logo]()
$106
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/246:57 pm
BOS
- SXM
1 stop18h 53m
American Airlines
Deal found 4/27![American Airlines logo]()
$107
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/266:00 am
BOS
- MBJ
1 stop7h 11m
Frontier
Deal found 4/28![Frontier logo]()
$108
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 April 29, 2026.
Round-trip from | $192 (eDestinos) |
|---|---|
One-way from | $94 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $345 |
Good round-trip deal | $330 or less |
Good one-way deal | $124 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 April 29, 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
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Sat 5/30
6:00 am-2:06 pm
1 stop8h 06m
Simpson Bay Princess Juliana
Sat 6/6
3:45 pm-7:24 am
1 stop15h 39m
$297
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Sat 6/6
7:30 am-3:25 pm
1 stop7h 55m
Bridgetown Grantley Adams Intl
Sat 6/13
3:05 pm-11:59 pm
1 stop8h 54m
$304
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Wed 5/27
5:35 am-2:20 pm
1 stop8h 45m
Bridgetown Grantley Adams Intl
Tue 6/2
3:40 pm-1:28 am
1 stop9h 48m
$304
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Sat 5/23
5:45 am-1:50 pm
1 stop8h 05m
Bridgetown Grantley Adams Intl
Sat 5/30
4:35 pm-9:12 am
1 stop16h 37m
$304
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Fri 5/29
5:35 am-2:20 pm
1 stop8h 45m
Bridgetown Grantley Adams Intl
Tue 6/2
3:40 pm-1:28 am
1 stop9h 48m
$304
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Mon 8/24
5:45 am-1:56 pm
1 stop8h 11m
Simpson Bay Princess Juliana
Fri 8/28
3:21 pm-1:06 am
1 stop9h 45m
$305
BostonBridgetown
BOS - BGI
BOSBGI
Boston Logan Intl
Sat 5/9
6:00 am-3:25 pm
1 stop9h 25m
Bridgetown Grantley Adams Intl
Sat 5/16
4:35 pm-7:53 am
1 stop15h 18m
$311
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Tue 7/21
5:30 am-1:11 pm
1 stop7h 41m
San Juan Luis Munoz Marin Intl
Tue 7/28
5:56 pm-1:20 am
1 stop7h 24m
$312
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Sat 5/9
6:00 am-2:06 pm
1 stop8h 06m
Simpson Bay Princess Juliana
Sat 5/16
3:35 pm-7:22 am
1 stop15h 47m
$314
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Wed 7/15
5:45 am-12:33 pm
1 stop6h 48m
Simpson Bay Princess Juliana
Thu 7/23
3:50 pm-8:17 am
2 stops16h 27m
$316
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-SXM
BOS-SJU
BOS-BGI
BOS-MBJ
BOS-NAS
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-SXM
BOS-SJU
BOS-BGI
BOS-MBJ
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 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 $411). Flying from Boston to Caribbean in December is currently the most expensive (average of $576). 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 April 29, 2026.
It’s typically best to fly out from Boston to Caribbean in the afternoon. Doing so could potentially save you 26% on the flight price compared to flying at noon, which is usually more expensive.
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 April 25, 2026.
Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Boston to Caribbean
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 April 29, 2026.
The most flights from BOS to 0CB are scheduled on a Monday (14 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
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 April 29, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue 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
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for 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 April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$477 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$93 | Average$360 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$129 | Average$601 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$145 | Average$470 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$152 | Average$513 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$342 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$178 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$242 | Average$578 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$570 | FlexibilityNo cancel fee | On-time63% |