$111+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Jul 4 — Jul 111
Round-trip
1 adult, Economy
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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
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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 June 4, 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 June 4, 2026.
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Sat 8/297:30 am
BOS
- STT
1 stop8h 13m
United Airlines
Sat 9/54:45 pm
STT
- BOS
1 stop7h 14m
United Airlines
Deal found 6/2![United Airlines logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 6/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 7/142:53 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/2![JetBlue logo]()
$296
This Super.com deal was found by Cheapflights users on 6/3. 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.
Thu 9/247:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Wed 9/307:35 pm
SJU
- BOS
Nonstop4h 08m
JetBlue
Deal found 6/3![JetBlue logo]()
$297
This Cheapflightsfares deal was found by Cheapflights users on 6/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:20 pm
BOS
- SJU
Nonstop4h 38m
JetBlue
Fri 9/257:35 pm
SJU
- BOS
Nonstop4h 08m
JetBlue
Deal found 6/3![JetBlue logo]()
$298
This JetBlue deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/1610:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 6/232:58 pm
STT
- BOS
1 stop5h 39m
JetBlue
Deal found 5/31![JetBlue logo]()
$301
This Super.com deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Mon 11/97:25 pm
BOS
- SJU
Nonstop4h 00m
JetBlue
Wed 11/188:45 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 5/31![JetBlue logo]()
$302
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:55 am
BOS
- STT
Nonstop4h 05m
JetBlue
Fri 7/102:49 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/2![JetBlue logo]()
$302
This Delta deal was found by Cheapflights users on 6/2. 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.
Tue 10/278:15 am
BOS
- SJU
Nonstop4h 06m
Delta
Wed 11/42:32 pm
SJU
- BOS
Nonstop4h 13m
Delta
Deal found 6/2![Delta logo]()
$303
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Sat 8/296:00 am
BOS
- SJU
2 stops8h 51m
American Airlines
Sat 8/297:20 pm
SJU
- BOS
1 stop14h 59m
American Airlines
Deal found 6/3![American Airlines logo]()
$307
This Delta deal was found by Cheapflights users on 6/2. 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.
Thu 9/38:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Sun 9/137:00 am
SJU
- BOS
1 stop8h 19m
Delta
Deal found 6/2![Delta logo]()
$308
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Thu 8/205:00 am
BOS
- STT
1 stop7h 53m
American Airlines
Sat 8/293:43 pm
STT
- BOS
1 stop17h 39m
American Airlines
Deal found 6/3![American Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 6/1. 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.
Tue 8/186:05 am
BOS
- SJU
1 stop10h 28m
Delta
Sat 8/295:49 pm
SJU
- BOS
1 stop7h 36m
Delta
Deal found 6/1![Delta 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 June 4, 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 June 4, 2026.
This JetBlue deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/1610:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 6/232:58 pm
STT
- BOS
1 stop5h 39m
JetBlue
Deal found 5/31![JetBlue logo]()
$301
This Delta deal was found by Cheapflights users on 6/2. 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.
Sat 7/46:06 am
BOS
- SXM
1 stop8h 09m
Delta
Sat 7/113:35 pm
SXM
- BOS
1 stop15h 51m
Delta
Deal found 6/2![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/237:19 am
BOS
- NAS
1 stop7h 38m
United Airlines
Sat 6/271:15 pm
NAS
- BOS
1 stop5h 57m
United Airlines
Deal found 5/31![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 6/3. 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.
Thu 8/1312:40 pm
BOS
- SJU
2 stops10h 25m
Southwest
Tue 8/186:00 am
SJU
- BOS
1 stop6h 40m
Southwest
Deal found 6/3![Southwest logo]()
$412
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Wed 7/86:00 am
BOS
- SXM
2 stops9h 44m
American Airlines
Mon 7/134:45 pm
SXM
- BOS
2 stops17h 10m
American Airlines
Deal found 6/3![American Airlines logo]()
$455
This Copa Airlines deal was found by Cheapflights users on 6/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:55 pm
BOS
- AUA
1 stop20h 15m
Copa Airlines
Sun 10/257:05 am
AUA
- BOS
1 stop15h 57m
Copa Airlines
Deal found 6/3![Copa Airlines logo]()
$463
This Arajet deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1810:20 pm
BOS
- SDQ
Nonstop4h 15m
Arajet
Thu 7/24:35 pm
SDQ
- BOS
Nonstop4h 15m
Arajet
Deal found 5/31![Arajet logo]()
$479
This Expedia deal was found by Cheapflights users on 6/3. 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.
Sat 7/256:00 am
BOS
- SXM
1 stop11h 00m
Multiple Airlines
Sat 8/112:43 pm
SXM
- BOS
1 stop20h 26m
Multiple Airlines
Deal found 6/3![Multiple Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/32:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 5/31![Delta logo]()
$343
This JetBlue deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2311:45 am
BOS
- AUA
Nonstop4h 55m
JetBlue
Thu 8/276:00 pm
AUA
- BOS
Nonstop4h 54m
JetBlue
Deal found 5/30![JetBlue logo]()
$377
This Delta deal was found by Cheapflights users on 6/3. 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.
Sun 8/168:50 am
BOS
- SJU
Nonstop4h 07m
Delta
Thu 8/202:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 6/3![Delta logo]()
$343
This United Airlines deal was found by Cheapflights users on 6/4. 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.
Mon 8/36:00 am
BOS
- NAS
1 stop8h 57m
United Airlines
Fri 8/73:59 pm
NAS
- BOS
1 stop7h 22m
United Airlines
Deal found 6/4![United Airlines logo]()
$386
This JetBlue deal was found by Cheapflights users on 6/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:39 am
BOS
- AUA
Nonstop4h 56m
JetBlue
Fri 9/185:00 pm
AUA
- BOS
Nonstop4h 52m
JetBlue
Deal found 6/2![JetBlue logo]()
$377
This Southwest deal was found by Cheapflights users on 6/3. 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.
Fri 7/310:15 pm
BOS
- SXM
2 stops16h 50m
Southwest
Fri 7/102:25 pm
SXM
- BOS
2 stops17h 40m
Southwest
Deal found 6/3![Southwest logo]()
$416
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/136:05 am
BOS
- SJU
1 stop10h 28m
Delta
Mon 8/172:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 5/30![Delta logo]()
$348
This United Airlines deal was found by Cheapflights users on 6/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:05 am
BOS
- NAS
1 stop7h 24m
United Airlines
Sun 7/193:59 pm
NAS
- BOS
1 stop9h 15m
United Airlines
Deal found 6/3![United Airlines logo]()
$386
This JetBlue deal was found by Cheapflights users on 6/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:36 am
BOS
- AUA
Nonstop4h 54m
JetBlue
Wed 8/262:25 pm
AUA
- BOS
Nonstop4h 56m
JetBlue
Deal found 6/2![JetBlue logo]()
$377
This Copa Airlines deal was found by Cheapflights users on 6/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:41 am
BOS
- AUA
1 stop13h 24m
Copa Airlines
Sun 11/87:10 am
AUA
- BOS
1 stop15h 51m
Copa Airlines
Deal found 6/3![Copa Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/141:34 pm
BOS
- SJU
1 stop10h 18m
Delta
Mon 8/172:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 5/30![Delta logo]()
$348
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Sun 7/195:45 am
BOS
- PLS
1 stop10h 20m
United Airlines
Thu 7/235:15 pm
PLS
- BOS
2 stops15h 02m
United Airlines
Deal found 6/2![United Airlines logo]()
$396
This Southwest deal was found by Cheapflights users on 6/3. 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.
Fri 7/1010:25 pm
BOS
- SXM
2 stops16h 40m
Southwest
Tue 7/143:00 pm
SXM
- BOS
2 stops18h 50m
Southwest
Deal found 6/3![Southwest logo]()
$444
This JetBlue deal was found by Cheapflights users on 6/3. 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.
Mon 8/2410:36 am
BOS
- AUA
Nonstop4h 54m
JetBlue
Thu 9/31:55 pm
AUA
- BOS
Nonstop4h 57m
JetBlue
Deal found 6/3![JetBlue logo]()
$377
This Copa Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/174:00 pm
BOS
- PUJ
1 stop22h 04m
Copa Airlines
Mon 6/2211:46 am
PUJ
- BOS
1 stop11h 22m
Copa Airlines
Deal found 5/30![Copa Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 6/2. 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.
Sat 8/86:05 am
BOS
- SJU
1 stop10h 28m
Delta
Sat 8/155:49 pm
SJU
- BOS
1 stop7h 36m
Delta
Deal found 6/2![Delta logo]()
$352
This United Airlines deal was found by Cheapflights users on 6/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/239:30 am
BOS
- PLS
1 stop6h 35m
United Airlines
Sun 6/283:30 pm
PLS
- BOS
2 stops17h 59m
United Airlines
Deal found 6/3![United Airlines logo]()
$400
This JetBlue deal was found by Cheapflights users on 6/1. 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.
Mon 8/3110:36 am
BOS
- AUA
Nonstop4h 54m
JetBlue
Fri 9/46:00 pm
AUA
- BOS
Nonstop4h 54m
JetBlue
Deal found 6/1![JetBlue logo]()
$377
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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
2 stops8h 00m
Southwest
Mon 8/3112:15 pm
MBJ
- BOS
2 stops20h 40m
Southwest
Deal found 5/30![Southwest logo]()
$457
This Copa Airlines deal was found by Cheapflights users on 6/3. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/23:57 pm
BOS
- PUJ
1 stop22h 59m
Copa Airlines
Fri 7/1011:46 am
PUJ
- BOS
1 stop26h 48m
Copa Airlines
Deal found 6/3![Copa Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 6/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:00 am
BOS
- SJU
2 stops14h 38m
United Airlines
Tue 8/257:00 am
SJU
- BOS
2 stops16h 35m
United Airlines
Deal found 6/3![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 6/2. 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.
Wed 6/177:00 am
BOS
- SDQ
1 stop11h 04m
Delta
Fri 6/267:35 pm
SDQ
- BOS
1 stop12h 47m
Delta
Deal found 6/2![Delta logo]()
$369
Last-minute flights from Boston to Caribbean IslandsDiscover last-minute flight deals from Boston to Caribbean Islands. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated June 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/138:50 am
BOS
- SJU
Nonstop4h 04m
Delta
Fri 6/192:05 pm
SJU
- BOS
Nonstop4h 09m
Delta
Deal found 5/30![Delta logo]()
$303
This Cheapflightsfares deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
Mon 6/159:44 pm
BOS
- SJU
Nonstop4h 00m
JetBlue
Fri 6/199:15 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 5/30![JetBlue logo]()
$298
This Cheapflightsfares deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Mon 6/159:44 pm
BOS
- SJU
Nonstop4h 00m
JetBlue
Wed 6/178:30 am
SJU
- BOS
Nonstop4h 03m
JetBlue
Deal found 5/31![JetBlue logo]()
$318
This JetBlue deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 6/1610:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Fri 6/193:18 pm
STT
- BOS
1 stop5h 39m
JetBlue
Deal found 5/31![JetBlue logo]()
$301
This Expedia deal was found by Cheapflights users on 6/2. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:55 am
BOS
- STT
Nonstop4h 05m
JetBlue
Fri 7/102:49 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/2![JetBlue logo]()
$302
This Cheapflightsfares deal was found by Cheapflights users on 6/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:55 am
BOS
- STT
Nonstop4h 05m
JetBlue
Tue 8/182:58 pm
STT
- BOS
1 stop5h 39m
JetBlue
Deal found 6/3![JetBlue logo]()
$316
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:06 am
BOS
- SXM
1 stop8h 09m
Delta
Sat 7/113:35 pm
SXM
- BOS
1 stop16h 48m
Delta
Deal found 5/31![Delta logo]()
$329
This Cheapflightsfares deal was found by Cheapflights users on 6/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:00 am
BOS
- STT
Nonstop4h 03m
JetBlue
Tue 7/142:53 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 6/2![JetBlue logo]()
$296
This JetBlue deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:56 am
BOS
- STT
Nonstop4h 03m
JetBlue
Fri 7/172:49 pm
STT
- BOS
1 stop5h 38m
JetBlue
Deal found 5/30![JetBlue logo]()
$321
This SmartFares deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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.
Wed 7/224:31 pm
BOS
- SJU
1 stop6h 25m
JetBlue
Tue 7/287:59 pm
SJU
- BOS
Nonstop4h 05m
JetBlue
Deal found 5/31![JetBlue logo]()
$327
This Delta deal was found by Cheapflights users on 6/2. 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.
Tue 7/289:05 am
BOS
- SJU
1 stop7h 33m
Delta
Thu 8/62:10 pm
SJU
- BOS
Nonstop4h 11m
Delta
Deal found 6/2![Delta logo]()
$308
This Delta deal was found by Cheapflights users on 6/2. 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.
Tue 7/289:05 am
BOS
- SJU
1 stop7h 33m
Delta
Sat 8/15:50 pm
SJU
- BOS
1 stop7h 30m
Delta
Deal found 6/2![Delta logo]()
$312
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 June 4, 2026.
Search for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 4, 2026.
This Super.com deal was found by Cheapflights users on 6/1. 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.
Wed 6/1711:45 am
BOS
- PLS
Nonstop3h 55m
JetBlue
Deal found 6/1![JetBlue logo]()
$111
This United Airlines deal was found by Cheapflights users on 6/2. 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.
Sat 7/116:00 am
BOS
- STT
2 stops11h 00m
United Airlines
Deal found 6/2![United Airlines logo]()
$113
This JetBlue deal was found by Cheapflights users on 6/1. 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.
Wed 7/111:45 am
BOS
- PLS
Nonstop3h 55m
JetBlue
Deal found 6/1![JetBlue logo]()
$114
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Tue 6/306:00 am
BOS
- PLS
1 stop8h 12m
American Airlines
Deal found 6/3![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Wed 7/156:00 am
BOS
- PLS
2 stops8h 15m
American Airlines
Deal found 6/3![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Mon 7/137:27 pm
BOS
- PLS
2 stops15h 13m
American Airlines
Deal found 6/3![American Airlines logo]()
$124
This Delta deal was found by Cheapflights users on 6/2. 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.
Fri 8/285:30 am
BOS
- SXM
1 stop8h 23m
Delta
Deal found 6/2![Delta logo]()
$124
This Delta deal was found by Cheapflights users on 6/2. 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.
Fri 6/199:29 pm
BOS
- SXM
1 stop16h 46m
Delta
Deal found 6/2![Delta logo]()
$131
This JetBlue deal was found by Cheapflights users on 6/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2611:45 am
BOS
- PLS
Nonstop3h 55m
JetBlue
Deal found 6/2![JetBlue logo]()
$134
This American Airlines deal was found by Cheapflights users on 6/3. 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.
Thu 7/306:00 am
BOS
- PLS
2 stops8h 15m
American Airlines
Deal found 6/3![American Airlines logo]()
$138
This United Airlines deal was found by Cheapflights users on 6/4. 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.
Fri 8/75:45 am
BOS
- STT
1 stop6h 35m
United Airlines
Deal found 6/4![United Airlines logo]()
$138
This FlipMilhas deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlipMilhas is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:00 am
BOS
- NAS
1 stop11h 55m
GOL
Deal found 5/30![GOL logo]()
$141
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 June 4, 2026.
Round-trip from | $230 (United Airlines) |
|---|---|
One-way from | $111 (Super.com) |
Popular in | December |
Cheapest in | January |
Average price | $364 |
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 June 4, 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
Tue 6/16
10:00 am-2:03 pm
Nonstop4h 03m
Saint Thomas Island Cyril E King
Tue 6/23
2:58 pm-8:37 pm
1 stop5h 39m
$301
BostonSimpson Bay
BOS - SXM
BOSSXM
Boston Logan Intl
Sat 7/4
6:06 am-2:15 pm
1 stop8h 09m
Simpson Bay Princess Juliana
Sat 7/11
3:35 pm-7:26 am
1 stop15h 51m
$337
Quickest round-trip
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Thu 8/27
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Thu 9/3
2:10 pm-6:21 pm
Nonstop4h 11m
$343
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sun 8/16
8:50 am-12:57 pm
Nonstop4h 07m
San Juan Luis Munoz Marin Intl
Thu 8/20
2:10 pm-6:21 pm
Nonstop4h 11m
$343
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Thu 8/13
6:05 am-4:33 pm
1 stop10h 28m
San Juan Luis Munoz Marin Intl
Mon 8/17
2:10 pm-6:21 pm
Nonstop4h 11m
$348
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Fri 8/14
1:34 pm-11:52 pm
1 stop10h 18m
San Juan Luis Munoz Marin Intl
Mon 8/17
2:10 pm-6:21 pm
Nonstop4h 11m
$348
BostonSan Juan
BOS - SJU
BOSSJU
Boston Logan Intl
Sat 8/8
6:05 am-4:33 pm
1 stop10h 28m
San Juan Luis Munoz Marin Intl
Sat 8/15
5:49 pm-1:25 am
1 stop7h 36m
$352
BostonSanto Domingo
BOS - SDQ
BOSSDQ
Boston Logan Intl
Wed 6/17
7:00 am-6:04 pm
1 stop11h 04m
Santo Domingo Las Americas
Fri 6/26
7:35 pm-8:22 am
1 stop12h 47m
$369
BostonOranjestad
BOS - AUA
BOSAUA
Boston Logan Intl
Sun 8/23
11:45 am-4:40 pm
Nonstop4h 55m
Oranjestad Reina Beatrix
Thu 8/27
6:00 pm-10:54 pm
Nonstop4h 54m
$377
BostonOranjestad
BOS - AUA
BOSAUA
Boston Logan Intl
Mon 9/7
7:39 am-12:35 pm
Nonstop4h 56m
Oranjestad Reina Beatrix
Fri 9/18
5:00 pm-9:52 pm
Nonstop4h 52m
$377
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-STT
BOS-SJU
BOS-SXM
BOS-NAS
BOS-AUA
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-STT
BOS-SJU
BOS-SXM
BOS-NAS
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 $453). Flying from Boston to Caribbean Islands in December is currently the most expensive (average of $695). 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 June 4, 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 22% 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 June 4, 2026.
The most flights from BOS to zzEPX are scheduled on a Wednesday (10 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 41 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 May 30, 2026.
Travelers seeking maximum savings on their Boston to Caribbean Islands flight should consider departing on Friday 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 June 4, 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.
Crew
8.5
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Overall
7.9
Entertainment
7.8
Food
7.2
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean 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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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 June 4, 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 June 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$86 | Average$442 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$506 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$146 | Average$468 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$516 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$166 | Average$462 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$176 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$382 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$242 | Average$577 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$313 | Average$569 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$317 | Average$537 | FlexibilityNo cancel fee | On-timeN/A |