$79+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
abr. 5 — abr. 121
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Caribbean Islands with Cheapflights
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Cheapest flights from Boston to Caribbean IslandsExplore the most affordable flight options available from Boston to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on marzo 6, 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 marzo 6, 2026.
This Expedia deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
mar. 3/243:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
mar. 3/3110:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
dom. 3/293:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
jue. 4/26:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$158
This Priceline deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mar. 4/711:18 am
BOS
- SJU
Nonstop3h 59m
Frontier
jue. 4/96:00 am
SJU
- BOS
Nonstop4h 16m
Frontier
Deal found 3/2![Frontier logo]()
$160
This CheapOair deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/183:47 pm
BOS
- SJU
Nonstop3h 54m
Spirit Airlines
sáb. 8/223:29 pm
SJU
- BOS
Nonstop4h 07m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mar. 4/711:18 am
BOS
- SJU
Nonstop3h 59m
Multiple Airlines
jue. 4/1610:25 am
SJU
- BOS
Nonstop4h 07m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
lun. 3/233:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
sáb. 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$163
This Gotogate deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/233:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
mié. 4/110:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$165
This CheapOair deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/293:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
sáb. 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$166
This CheapOair deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/303:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
sáb. 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mié. 8/1910:40 am
BOS
- SJU
Nonstop3h 54m
Spirit Airlines
vie. 8/283:29 pm
SJU
- BOS
Nonstop4h 07m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$169
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mié. 4/18:40 am
BOS
- STT
Nonstop4h 03m
Delta
mié. 4/82:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Deal found 3/2![Delta logo]()
$201
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mar. 3/175:35 am
BOS
- STT
1 stop9h 10m
Delta
mié. 3/252:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Deal found 3/2![Delta logo]()
$206
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 marzo 6, 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 marzo 6, 2026.
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mié. 3/258:40 am
BOS
- STT
Nonstop4h 03m
Delta
mié. 4/12:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Deal found 3/1![Delta logo]()
$201
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
sáb. 5/95:45 am
BOS
- STT
2 stops11h 15m
United Airlines
mar. 5/121:22 pm
STT
- BOS
1 stop10h 13m
United Airlines
Deal found 3/4![United Airlines logo]()
$230
This JetBlue deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
mar. 5/58:00 am
BOS
- SJU
Nonstop4h 00m
JetBlue
dom. 5/106:45 pm
SJU
- BOS
Nonstop4h 09m
JetBlue
Deal found 3/6![JetBlue logo]()
$283
This Southwest deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
sáb. 4/254:50 pm
BOS
- SJU
1 stop6h 25m
Southwest
mar. 5/125:35 am
SJU
- BOS
2 stops10h 20m
Southwest
Deal found 3/4![Southwest logo]()
$318
This Copa Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
dom. 5/38:52 am
BOS
- AUA
1 stop13h 05m
Copa Airlines
dom. 5/107:19 am
AUA
- BOS
1 stop15h 49m
Copa Airlines
Deal found 3/4![Copa Airlines logo]()
$325
This Arajet deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
jue. 8/2710:20 pm
BOS
- SDQ
Nonstop4h 15m
Arajet
dom. 8/304:35 pm
SDQ
- BOS
Nonstop4h 15m
Arajet
Deal found 3/4![Arajet logo]()
$365
This Avianca deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
jue. 4/308:45 am
BOS
- PUJ
1 stop32h 40m
Avianca
mié. 5/66:00 pm
PUJ
- BOS
1 stop13h 10m
Avianca
Deal found 3/4![Avianca logo]()
$402
This Priceline deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
jue. 4/95:30 am
BOS
- MBJ
1 stop9h 53m
Multiple Airlines
jue. 4/168:41 am
MBJ
- BOS
1 stop13h 05m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
dom. 3/298:40 am
BOS
- STT
Nonstop4h 03m
Delta
vie. 4/32:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Deal found 3/6![Delta logo]()
$221
This United Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
mié. 6/35:45 am
BOS
- AUA
2 stops10h 55m
United Airlines
mié. 6/104:30 pm
AUA
- BOS
1 stop7h 29m
United Airlines
Deal found 3/4![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
sáb. 5/98:50 am
BOS
- SJU
Nonstop3h 59m
Delta
sáb. 5/162:00 pm
SJU
- BOS
Nonstop4h 18m
Delta
Deal found 3/3![Delta logo]()
$283
This Southwest deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
dom. 4/265:30 am
BOS
- SXM
1 stop7h 10m
Southwest
vie. 5/12:25 pm
SXM
- BOS
2 stops17h 40m
Southwest
Deal found 3/3![Southwest logo]()
$347
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
jue. 5/79:05 am
BOS
- SDQ
1 stop8h 56m
Delta
jue. 5/147:35 pm
SDQ
- BOS
1 stop11h 47m
Delta
Deal found 3/1![Delta logo]()
$291
This JetBlue deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
dom. 5/36:35 am
BOS
- SDQ
1 stop7h 16m
JetBlue
mié. 5/63:01 pm
SDQ
- BOS
1 stop9h 13m
JetBlue
Deal found 3/3![JetBlue logo]()
$361
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mié. 4/155:45 am
BOS
- SXM
1 stop6h 48m
United Airlines
mié. 4/223:50 pm
SXM
- BOS
2 stops17h 35m
United Airlines
Deal found 3/1![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mar. 5/56:00 am
BOS
- SDQ
1 stop12h 34m
Delta
jue. 5/147:35 pm
SDQ
- BOS
1 stop11h 47m
Delta
Deal found 3/1![Delta logo]()
$291
This Copa Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
jue. 5/284:00 pm
BOS
- PUJ
1 stop18h 39m
Copa Airlines
lun. 6/111:46 am
PUJ
- BOS
1 stop11h 22m
Copa Airlines
Deal found 3/2![Copa Airlines logo]()
$392
This FlightHub deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/83:42 pm
BOS
- STI
1 stop16h 20m
JetBlue
mié. 4/159:12 am
STI
- BOS
1 stop15h 02m
JetBlue
Deal found 3/1![JetBlue logo]()
$365
This Southwest deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
lun. 5/257:20 am
BOS
- NAS
2 stops11h 10m
Southwest
vie. 5/298:45 am
NAS
- BOS
2 stops11h 20m
Southwest
Deal found 3/1![Southwest logo]()
$370
This United Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mié. 3/255:45 am
BOS
- SXM
1 stop7h 05m
United Airlines
mar. 3/313:50 pm
SXM
- BOS
2 stops20h 56m
United Airlines
Deal found 3/2![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
sáb. 4/188:00 pm
BOS
- SDQ
1 stop16h 31m
Delta
jue. 4/237:59 pm
SDQ
- BOS
1 stop11h 26m
Delta
Deal found 3/2![Delta logo]()
$301
This Copa Airlines deal was found by Cheapflights users on 3/4. Clicking the “Pick Dates” 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.
sáb. 5/28:52 am
BOS
- PUJ
1 stop17h 15m
Copa Airlines
dom. 5/1011:44 am
PUJ
- BOS
1 stop11h 24m
Copa Airlines
Deal found 3/4![Copa Airlines logo]()
$402
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mar. 5/125:40 pm
BOS
- STI
1 stop14h 23m
JetBlue
dom. 5/173:34 am
STI
- BOS
Nonstop3h 51m
JetBlue
Deal found 3/1![JetBlue logo]()
$366
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
sáb. 5/26:00 am
BOS
- NAS
1 stop8h 08m
United Airlines
mar. 5/52:53 pm
NAS
- BOS
1 stop8h 42m
United Airlines
Deal found 3/1![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
jue. 5/79:05 am
BOS
- SDQ
1 stop8h 56m
Delta
sáb. 5/166:05 am
SDQ
- BOS
1 stop16h 56m
Delta
Deal found 3/6![Delta logo]()
$301
This JetBlue deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
jue. 5/75:40 pm
BOS
- STI
1 stop14h 23m
JetBlue
jue. 5/141:57 pm
STI
- BOS
Nonstop3h 59m
JetBlue
Deal found 3/1![JetBlue logo]()
$366
This Arajet deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
dom. 6/2810:20 pm
BOS
- PUJ
1 stop13h 05m
Multiple Airlines
jue. 7/22:05 am
PUJ
- BOS
1 stop8h 40m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$490
This Copa Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
vie. 5/158:52 am
BOS
- PUJ
1 stop17h 15m
Copa Airlines
mar. 5/1912:05 pm
PUJ
- BOS
1 stop11h 03m
Copa Airlines
Deal found 3/6![Copa Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
lun. 5/256:00 am
BOS
- NAS
1 stop7h 33m
United Airlines
vie. 5/293:59 pm
NAS
- BOS
1 stop9h 00m
United Airlines
Deal found 3/1![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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.
jue. 4/95:05 pm
BOS
- SXM
2 stops20h 25m
Southwest
mar. 4/142:25 pm
SXM
- BOS
2 stops17h 50m
Southwest
Deal found 3/6![Southwest logo]()
$429
Last-minute flights from Boston to Caribbean IslandsDiscover last-minute flight deals from Boston to Caribbean Islands. Data last updated marzo 6, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated marzo 6, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
lun. 3/165:40 am
BOS
- STT
1 stop6h 43m
American Airlines
mié. 3/252:03 pm
STT
- BOS
1 stop9h 20m
American Airlines
Deal found 3/2![American Airlines logo]()
$212
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mar. 3/175:35 am
BOS
- STT
1 stop9h 10m
Delta
mié. 3/252:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Deal found 3/2![Delta logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
lun. 3/233:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
sáb. 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$163
This Gotogate deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/233:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
mié. 4/110:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$165
This Expedia deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
mar. 3/243:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
mar. 3/3110:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
dom. 3/293:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
jue. 4/26:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/3![Multiple Airlines logo]()
$158
This CheapOair deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/293:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
sáb. 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$166
This CheapOair deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/303:23 pm
BOS
- SJU
Nonstop3h 56m
Multiple Airlines
sáb. 4/46:00 am
SJU
- BOS
Nonstop4h 16m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$167
This Super.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
mar. 3/313:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
mar. 4/710:00 am
SJU
- BOS
Nonstop4h 18m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$161
This Delta deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mié. 4/18:40 am
BOS
- STT
Nonstop4h 03m
Delta
mié. 4/82:45 pm
STT
- BOS
Nonstop4h 19m
Delta
Deal found 3/2![Delta logo]()
$201
This Priceline deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
mar. 4/711:18 am
BOS
- SJU
Nonstop3h 59m
Frontier
jue. 4/96:00 am
SJU
- BOS
Nonstop4h 16m
Frontier
Deal found 3/2![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mar. 4/711:18 am
BOS
- SJU
Nonstop3h 59m
Multiple Airlines
jue. 4/1610:25 am
SJU
- BOS
Nonstop4h 07m
Multiple Airlines
Deal found 3/1![Multiple Airlines logo]()
$162
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 marzo 6, 2026.
Search for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated marzo 6, 2026.
This American Airlines deal was found by Cheapflights users on 3/2. Clicking the “Pick Dates” 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.
lun. 6/16:00 am
BOS
- SXM
1 stop6h 40m
American Airlines
Deal found 3/2![American Airlines logo]()
$79
This Super.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mié. 3/183:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
vie. 4/242:12 pm
BOS
- SJU
Nonstop3h 54m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$80
This Expedia deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
dom. 3/223:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$81
This Expedia deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mar. 3/103:00 pm
BOS
- SJU
Nonstop4h 06m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$82
This American Airlines deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mar. 4/146:00 am
BOS
- SXM
2 stops9h 22m
American Airlines
Deal found 3/1![American Airlines logo]()
$84
This American Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
mar. 4/75:00 am
BOS
- SXM
1 stop10h 22m
American Airlines
Deal found 3/5![American Airlines logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
lun. 3/233:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 3/3![Spirit Airlines logo]()
$86
This CheapOair deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/13:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$87
This Booking.com deal was found by Cheapflights users on 3/1. Clicking the “Pick Dates” 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.
mié. 4/83:23 pm
BOS
- SJU
Nonstop3h 56m
Spirit Airlines
Deal found 3/1![Spirit Airlines logo]()
$88
This American Airlines deal was found by Cheapflights users on 3/3. Clicking the “Pick Dates” 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.
sáb. 5/96:22 pm
BOS
- SXM
1 stop17h 15m
American Airlines
Deal found 3/3![American Airlines logo]()
$89
This American Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
vie. 4/105:40 pm
BOS
- SXM
2 stops17h 57m
American Airlines
Deal found 3/5![American Airlines logo]()
$91
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 marzo 6, 2026.
Round-trip from | $155 (Expedia) |
|---|---|
One-way from | $79 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $269 |
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 marzo 6, 2026.
Use the filters below to find and compare flights from Boston to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
mié. 3/25
8:40 am-12:43 pm
Nonstop4h 03m
Saint Thomas Island Cyril E King
mié. 4/1
2:45 pm-7:04 pm
Nonstop4h 19m
$201
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
dom. 3/29
8:40 am-12:43 pm
Nonstop4h 03m
Saint Thomas Island Cyril E King
vie. 4/3
2:45 pm-7:04 pm
Nonstop4h 19m
$221
BostonSaint Thomas Island
BOS - STT
BOSSTT
Boston Logan Intl
sáb. 5/9
5:45 am-5:00 pm
2 stops11h 15m
Saint Thomas Island Cyril E King
mar. 5/12
1:22 pm-11:35 pm
1 stop10h 13m
$230
Quickest round-trip
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
mar. 5/5
8:00 am-12:00 pm
Nonstop4h 00m
San Juan Luis Munoz Marin Intl
dom. 5/10
6:45 pm-10:54 pm
Nonstop4h 09m
$283
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
sáb. 5/9
8:50 am-12:49 pm
Nonstop3h 59m
San Juan Luis Munoz Marin Intl
sáb. 5/16
2:00 pm-6:18 pm
Nonstop4h 18m
$283
BostonSanto Domingo
BOS - SDQ
BOSSDQ
Boston Logan Intl
jue. 5/7
9:05 am-6:01 pm
1 stop8h 56m
Santo Domingo Las Americas
jue. 5/14
7:35 pm-7:22 am
1 stop11h 47m
$291
BostonSanto Domingo
BOS - SDQ
BOSSDQ
Boston Logan Intl
mar. 5/5
6:00 am-6:34 pm
1 stop12h 34m
Santo Domingo Las Americas
jue. 5/14
7:35 pm-7:22 am
1 stop11h 47m
$291
BostonOranjestad
BOS - AUA
BOSAUA
Boston Logan Intl
mié. 6/3
5:45 am-4:40 pm
2 stops10h 55m
Oranjestad Reina Beatrix
mié. 6/10
4:30 pm-11:59 pm
1 stop7h 29m
$301
BostonSanto Domingo
BOS - SDQ
BOSSDQ
Boston Logan Intl
sáb. 4/18
8:00 pm-12:31 pm
1 stop16h 31m
Santo Domingo Las Americas
jue. 4/23
7:59 pm-7:25 am
1 stop11h 26m
$301
BostonSanto Domingo
BOS - SDQ
BOSSDQ
Boston Logan Intl
jue. 5/7
9:05 am-6:01 pm
1 stop8h 56m
Santo Domingo Las Americas
sáb. 5/16
6:05 am-11:01 pm
1 stop16h 56m
$301
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Boston with our price prediction graph.
BOS-SJU
BOS-STT
BOS-AUA
BOS-SDQ
BOS-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Boston to Caribbean Islands
BOS-zzEPX
BOS-SJU
BOS-STT
BOS-AUA
BOS-SDQ
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 $93). Flying from Boston to Caribbean Islands in November is currently the most expensive (average of $177). 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 marzo 6, 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.
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 February 21, 2026.
Travelers seeking maximum savings on their Boston to Caribbean Islands flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 marzo 6, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and JetBlue 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
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Comfort
7.9
Food
7.2
Overall
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 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 marzo 6, 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 marzo 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$430 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$88 | Average$337 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$130 | Average$621 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$141 | Average$449 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$502 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$466 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$366 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$184 | Average$371 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$242 | Average$577 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$348 | Average$645 | FlexibilityNo cancel fee | On-time63% |