$108+ Cheap flights from Boston (BOS) to Caribbean Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Oct 5 — Oct 121
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Boston to Caribbean Islands
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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 September 5, 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 September 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 10/276:00 am -
1 stop6h 50m
Tue 11/32:52 pm -
1 stop17h 51m
Deal found 9/2![United Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:52 pm -
2 stops13h 21m
Fri 10/27:15 am -
1 stop26h 14m
Deal found 9/2![Multiple Airlines logo]()
$286
This Cheapflightsfares deal was found by Cheapflights users on 8/31. 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.
Sat 10/177:42 pm -
Nonstop4h 07m
Sat 10/246:20 am -
Nonstop4h 04m
Deal found 8/31![JetBlue logo]()
$298
This FlightHub deal was found by Cheapflights users on 9/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:17 am -
1 stop11h 56m
Wed 9/306:42 pm -
1 stop15h 40m
Deal found 9/2![Frontier logo]()
$299
This CheapOair deal was found by Cheapflights users on 9/1. 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.
Tue 9/227:55 am -
Nonstop4h 07m
Wed 9/306:42 pm -
1 stop15h 40m
Deal found 9/1![Multiple Airlines logo]()
$301
This Priceline deal was found by Cheapflights users on 9/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:57 am -
1 stop10h 38m
Fri 12/258:20 am -
Nonstop4h 19m
Deal found 9/3![Frontier logo]()
$302
This United Airlines deal was found by Cheapflights users on 9/2. 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 12/126:00 am -
1 stop8h 57m
Sat 12/195:00 pm -
1 stop7h 59m
Deal found 9/2![United Airlines logo]()
$305
This Priceline deal was found by Cheapflights users on 9/2. 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.
Mon 12/72:21 pm -
Nonstop4h 06m
Fri 12/258:20 am -
Nonstop4h 19m
Deal found 9/2![Multiple Airlines logo]()
$305
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 10/278:05 pm -
1 stop16h 45m
Wed 11/42:52 pm -
1 stop17h 51m
Deal found 9/2![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 9/1. 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.
Fri 10/308:50 am -
Nonstop4h 02m
Fri 11/63:02 pm -
Nonstop4h 13m
Deal found 9/1![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 9/1. 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.
Fri 9/258:55 am -
Nonstop4h 02m
Thu 10/12:10 pm -
Nonstop4h 13m
Deal found 9/1![Delta logo]()
$309
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:55 am -
Nonstop4h 07m
Wed 9/306:42 pm -
1 stop15h 40m
Deal found 9/2![Multiple Airlines logo]()
$311
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 September 5, 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 September 5, 2026.
This Delta deal was found by Cheapflights users on 9/1. 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.
Wed 9/238:55 am -
Nonstop4h 02m
Tue 9/291:16 pm -
1 stop9h 54m
Deal found 9/1![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Wed 9/307:01 am -
2 stops13h 37m
Sat 10/31:00 am -
1 stop7h 47m
Deal found 9/1![United Airlines logo]()
$316
This Arajet deal was found by Cheapflights users on 8/31. 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.
Wed 10/1412:15 pm -
Nonstop4h 15m
Wed 10/286:24 am -
Nonstop4h 21m
Deal found 8/31![Arajet logo]()
$375
This JetBlue deal was found by Cheapflights users on 9/1. 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.
Thu 10/225:44 pm -
1 stop8h 20m
Fri 10/303:07 am -
Nonstop4h 12m
Deal found 9/1![JetBlue logo]()
$383
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 11/64:56 pm -
1 stop17h 20m
Tue 11/1011:16 am -
1 stop8h 19m
Deal found 9/1![American Airlines logo]()
$385
This Air Canada deal was found by Cheapflights users on 9/4. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:15 am -
1 stop25h 10m
Mon 11/21:05 pm -
2 stops25h 48m
Deal found 9/4![Air Canada logo]()
$394
This Copa Airlines deal was found by Cheapflights users on 9/5. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:50 pm -
1 stop19h 40m
Mon 11/912:25 pm -
1 stop10h 36m
Deal found 9/5![Copa Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 9/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:35 am -
1 stop6h 25m
Fri 10/2312:00 pm -
2 stops19h 15m
Deal found 9/5![Southwest logo]()
$467
This Delta deal was found by Cheapflights users on 9/1. 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.
Sat 10/178:50 am -
Nonstop4h 02m
Fri 10/236:45 am -
1 stop8h 04m
Deal found 9/1![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 8/31. 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 10/137:38 am -
1 stop6h 07m
Mon 10/191:00 am -
2 stops13h 07m
Deal found 8/31![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 9/1. 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.
Wed 10/148:50 am -
Nonstop4h 02m
Sun 10/181:15 pm -
1 stop9h 53m
Deal found 9/1![Delta logo]()
$312
This United Airlines deal was found by Cheapflights users on 9/4. 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 10/166:00 am -
1 stop7h 45m
Mon 10/193:56 pm -
1 stop8h 58m
Deal found 9/4![United Airlines logo]()
$336
This JetBlue deal was found by Cheapflights users on 9/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:53 am -
Nonstop4h 57m
Mon 11/26:00 pm -
Nonstop5h 03m
Deal found 9/5![JetBlue logo]()
$401
This Delta deal was found by Cheapflights users on 9/3. 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.
Sat 9/265:40 am -
1 stop7h 36m
Fri 10/21:16 pm -
1 stop9h 54m
Deal found 9/3![Delta logo]()
$336
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Tue 10/272:40 pm -
1 stop6h 42m
Sat 10/317:05 am -
2 stops10h 40m
Deal found 9/4![United Airlines logo]()
$336
This Arajet deal was found by Cheapflights users on 9/3. 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.
Wed 11/1111:15 am -
Nonstop4h 22m
Sun 11/154:29 pm -
Nonstop4h 21m
Deal found 9/3![Arajet logo]()
$425
This Delta deal was found by Cheapflights users on 9/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:35 pm -
1 stop10h 09m
Tue 10/276:45 am -
1 stop8h 04m
Deal found 9/4![Delta logo]()
$336
This JetBlue deal was found by Cheapflights users on 9/1. 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 10/126:55 am -
1 stop5h 55m
Sun 10/181:00 pm -
1 stop11h 07m
Deal found 9/1![JetBlue logo]()
$408
This Copa Airlines deal was found by Cheapflights users on 9/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/142:43 pm -
1 stop19h 38m
Tue 1/1912:25 pm -
1 stop25h 57m
Deal found 9/1![Copa Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Fri 11/139:12 am -
1 stop10h 48m
Tue 11/171:00 pm -
1 stop6h 34m
Deal found 8/31![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 9/3. 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.
Wed 12/25:30 am -
2 stops8h 15m
Sun 12/62:40 pm -
2 stops17h 40m
Deal found 9/3![Southwest logo]()
$480
This American Airlines deal was found by Cheapflights users on 8/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/136:00 am -
1 stop9h 33m
Tue 1/191:01 pm -
2 stops11h 42m
Deal found 8/31![American Airlines logo]()
$481
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 10/238:50 am -
Nonstop4h 02m
Tue 11/33:59 pm -
1 stop10h 21m
Deal found 9/3![Delta logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/3. 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.
Sun 11/85:30 am -
1 stop7h 26m
Wed 11/111:07 pm -
2 stops9h 52m
Deal found 9/3![United Airlines logo]()
$360
This JetBlue deal was found by Cheapflights users on 8/31. 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 9/297:55 am -
1 stop6h 06m
Mon 10/53:00 pm -
1 stop8h 03m
Deal found 8/31![JetBlue logo]()
$436
This Southwest deal was found by Cheapflights users on 9/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:00 pm -
2 stops16h 05m
Mon 11/23:45 pm -
1 stop7h 45m
Deal found 9/2![Southwest logo]()
$526
This Delta deal was found by Cheapflights users on 9/3. 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.
Sat 9/198:55 am -
Nonstop4h 02m
Sat 9/262:10 pm -
Nonstop4h 13m
Deal found 9/3![Delta logo]()
$370
This American Airlines deal was found by Cheapflights users on 8/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/305:40 am -
1 stop7h 43m
Wed 10/72:23 pm -
1 stop10h 36m
Deal found 8/31![American Airlines logo]()
$543
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 10/296:00 am -
2 stops10h 00m
Mon 11/22:30 pm -
1 stop7h 29m
Deal found 9/2![United Airlines logo]()
$385
This Copa Airlines deal was found by Cheapflights users on 9/2. 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.
Sun 10/183:55 pm -
1 stop22h 45m
Fri 10/231:19 pm -
1 stop9h 43m
Deal found 9/2![Copa Airlines logo]()
$590
Last-minute flights from Boston to Caribbean IslandsDiscover last-minute flight deals from Boston to Caribbean Islands. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean Islands. Data last updated September 5, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 9/1. 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.
Tue 9/227:55 am -
Nonstop4h 07m
Wed 9/306:42 pm -
1 stop15h 40m
Deal found 9/1![Multiple Airlines logo]()
$301
This FlightHub deal was found by Cheapflights users on 9/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:17 am -
1 stop11h 56m
Wed 9/306:42 pm -
1 stop15h 40m
Deal found 9/2![Frontier logo]()
$299
This Delta deal was found by Cheapflights users on 9/1. 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.
Fri 9/258:55 am -
Nonstop4h 02m
Thu 10/12:10 pm -
Nonstop4h 13m
Deal found 9/1![Delta logo]()
$309
This CheapOair deal was found by Cheapflights users on 9/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:55 am -
Nonstop4h 07m
Wed 9/306:42 pm -
1 stop15h 40m
Deal found 9/2![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:52 pm -
2 stops13h 21m
Fri 10/27:15 am -
1 stop26h 14m
Deal found 9/2![Multiple Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 8/31. 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.
Tue 10/138:50 am -
Nonstop4h 02m
Wed 10/216:45 am -
1 stop8h 04m
Deal found 8/31![Delta logo]()
$312
This Cheapflightsfares deal was found by Cheapflights users on 8/31. 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.
Sat 10/177:42 pm -
Nonstop4h 07m
Sat 10/246:20 am -
Nonstop4h 04m
Deal found 8/31![JetBlue logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:57 pm -
2 stops21h 22m
Fri 10/306:15 am -
1 stop27h 14m
Deal found 9/2![Multiple Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 10/277:41 pm -
2 stops17h 09m
Tue 11/32:52 pm -
1 stop17h 51m
Deal found 9/2![United Airlines logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 10/277:41 pm -
2 stops17h 09m
Wed 11/42:52 pm -
1 stop17h 51m
Deal found 9/2![United Airlines logo]()
$305
This Cheapflightsfares deal was found by Cheapflights users on 9/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2711:00 am -
Nonstop4h 05m
Tue 10/277:40 pm -
Nonstop4h 18m
Deal found 9/1![JetBlue logo]()
$313
This Delta deal was found by Cheapflights users on 9/1. 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.
Fri 10/308:50 am -
Nonstop4h 02m
Fri 11/63:02 pm -
Nonstop4h 13m
Deal found 9/1![Delta logo]()
$307
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 September 5, 2026.
Search for one-way flight options from Boston to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated September 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/2. 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 12/126:00 am -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$108
This United Airlines deal was found by Cheapflights users on 9/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/48:33 pm -
2 stops18h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![United Airlines logo]()
$114
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Thu 12/317:49 pm -
1 stop17h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 9/3. 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 11/38:16 am -
2 stops9h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Tue 10/66:59 am -
2 stops10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![American Airlines logo]()
$131
This Air Canada deal was found by Cheapflights users on 9/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/265:30 am -
1 stop8h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Air Canada logo]()
$134
This Expedia deal was found by Cheapflights users on 9/3. 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.
Wed 9/167:40 pm -
2 stops17h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Air Canada logo]()
$134
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/146:00 am -
2 stops7h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 8/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:00 am -
2 stops10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![American Airlines logo]()
$136
This United Airlines deal was found by Cheapflights users on 9/2. 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.
Tue 11/176:00 am -
1 stop6h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$138
This Air Canada deal was found by Cheapflights users on 9/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:45 pm -
2 stops23h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Air Canada logo]()
$139
This Air Canada deal was found by Cheapflights users on 9/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1810:50 am -
1 stop6h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Air Canada logo]()
$139
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 September 5, 2026.
Round-trip from | $285 (United Airlines) |
|---|---|
One-way from | $108 (United Airlines) |
Popular in | July |
Cheapest in | January |
Average price | $316 |
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 7,457,451 searches. Data last updated September 5, 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
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sat 12/12
6:00 am-3:57 pm
1 stop8h 57m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Sat 10/24
6:30 pm-9:27 am
1 stop14h 57m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$130
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Tue 1/5
7:41 pm-1:50 pm
1 stop17h 09m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sat 1/9
7:41 pm-1:50 pm
1 stop17h 09m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$134
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Fri 12/11
8:25 pm-3:57 pm
1 stop18h 32m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Wed 10/28
6:00 am-12:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Tue 11/17
6:00 am-1:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$138
BostonProvidenciales
BOS Boston Logan Intl - PLS Providenciales
BOSPLS
Boston Logan Intl
Mon 11/30
10:40 am-1:25 pm
1 stop26h 45m
Providenciales
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
BostonProvidenciales
BOS Boston Logan Intl - PLS Providenciales
BOSPLS
Boston Logan Intl
Mon 11/30
5:25 am-1:45 pm
2 stops8h 20m
Providenciales
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$148
BostonProvidenciales
BOS Boston Logan Intl - PLS Providenciales
BOSPLS
Boston Logan Intl
Thu 11/26
11:15 am-12:25 pm
1 stop25h 10m
Providenciales
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$149
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Boston with our price prediction graph.
BOS-SXM
BOS-NAS
BOS-PLS
BOS-AUA
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-SXM
BOS-NAS
BOS-PLS
BOS-AUA
What is the cheapest month to book a flight from Boston to Caribbean Islands?
Currently, May is the cheapest month in which you can book a flight from Boston to Caribbean Islands (average of $471). Flying from Boston to Caribbean Islands in December is currently the most expensive (average of $676). 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 September 5, 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 21% on your trip compared to booking a flight at noon.
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 30 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 August 29, 2026.
Travelers seeking maximum savings on their Boston to Caribbean Islands flight should consider departing on Tuesday at noon when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Caribbean 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 September 5, 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.
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Overall
7.8
Boarding
8.1
Comfort
7.8
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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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 September 5, 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 9 airlines flying from Boston to Caribbean Islands
Discover the top 9 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 7,457,451 searches. Data last updated September 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$451 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$618 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$161 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$166 | Average$470 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$173 | Average$538 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$183 | Average$386 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$186 | Average$409 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$586 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$537 | FlexibilityNo cancel fee | On-timeN/A |