$108+ Cheap flights from Boston (BOS) to Caribbean
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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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Find cheap flights from Boston to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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Cheapest flights from Boston to CaribbeanExplore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
Explore the most affordable flight options available from Boston to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:19 am -
1 stop27h 12m
Fri 10/237:00 am -
1 stop26h 29m
Deal found 9/9![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:19 am -
1 stop26h 06m
Fri 11/137:00 am -
1 stop27h 29m
Deal found 9/8![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:19 am -
1 stop27h 06m
Fri 11/67:00 am -
1 stop27h 29m
Deal found 9/8![Multiple Airlines logo]()
$303
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 12/68:33 pm -
1 stop16h 17m
Thu 12/102:52 pm -
1 stop8h 03m
Deal found 9/7![United Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:39 pm -
1 stop11h 20m
Wed 11/118:45 am -
1 stop27h 59m
Deal found 9/8![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:19 am -
1 stop11h 36m
Sat 10/313:47 pm -
1 stop20h 57m
Deal found 9/7![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:36 am -
1 stop9h 12m
Fri 10/27:15 am -
1 stop26h 14m
Deal found 9/8![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:19 am -
1 stop11h 36m
Wed 10/216:42 pm -
1 stop16h 20m
Deal found 9/8![Multiple Airlines logo]()
$314
This Priceline deal was found by Cheapflights users on 9/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:17 am -
1 stop22h 18m
Wed 9/3010:42 am -
1 stop23h 40m
Deal found 9/6![Frontier logo]()
$316
This Super.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/287:55 am -
Nonstop4h 07m
Sun 10/116:20 am -
Nonstop4h 04m
Deal found 9/7![JetBlue logo]()
$317
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/137:01 pm -
1 stop17h 49m
Sat 12/195:00 pm -
1 stop18h 20m
Deal found 9/6![United Airlines logo]()
$335
This Expedia deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Thu 12/35:30 am -
1 stop8h 15m
Thu 12/103:45 pm -
1 stop19h 03m
Deal found 9/8![Air Canada logo]()
$339
Best flights from Boston to CaribbeanDiscover carefully curated flight deals from Boston to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
Discover carefully curated flight deals from Boston to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 10, 2026.
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 12/68:33 pm -
1 stop16h 17m
Thu 12/102:52 pm -
1 stop8h 03m
Deal found 9/7![United Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 9/6. 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.
Sun 11/158:35 am -
Nonstop4h 03m
Wed 11/182:50 pm -
Nonstop4h 16m
Deal found 9/6![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/122:25 pm -
2 stops9h 30m
Tue 11/176:40 am -
1 stop8h 50m
Deal found 9/9![Southwest logo]()
$367
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:30 am -
2 stops33h 15m
Thu 12/33:45 pm -
1 stop19h 03m
Deal found 9/9![Air Canada logo]()
$369
This Expedia deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Mon 11/165:45 am -
1 stop9h 00m
Sun 11/2211:30 am -
1 stop9h 20m
Deal found 9/9![Multiple Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/66:04 pm -
1 stop16h 12m
Tue 11/103:14 pm -
1 stop7h 45m
Deal found 9/10![American Airlines logo]()
$405
This JetBlue deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 2/28:00 am -
Nonstop4h 05m
Tue 2/92:00 pm -
Nonstop5h 49m
Deal found 9/8![JetBlue logo]()
$421
This Copa Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 -
1 stop13h 24m
Sun 11/87:10 am -
1 stop15h 51m
Deal found 9/7![Copa Airlines logo]()
$424
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.
Sat 10/247:13 pm -
2 stops17h 37m
Wed 10/281:52 pm -
1 stop8h 07m
Deal found 9/5![United Airlines logo]()
$310
This Delta deal was found by Cheapflights users on 9/6. 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.
Sun 9/278:55 am -
Nonstop4h 02m
Sat 10/32:10 pm -
Nonstop4h 13m
Deal found 9/6![Delta logo]()
$327
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.
Sat 10/247:13 pm -
2 stops17h 37m
Sat 10/311:10 pm -
2 stops19h 33m
Deal found 9/5![United Airlines logo]()
$310
This Southwest deal was found by Cheapflights users on 9/6. 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.
Fri 11/132:25 pm -
2 stops9h 30m
Tue 11/175:40 am -
2 stops9h 50m
Deal found 9/6![Southwest logo]()
$369
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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
Sat 10/246:45 am -
1 stop8h 04m
Deal found 9/8![Delta logo]()
$342
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/306:00 am -
1 stop7h 40m
Fri 11/65:50 pm -
1 stop7h 09m
Deal found 9/7![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/168:35 am -
Nonstop4h 03m
Mon 11/237:00 am -
1 stop8h 33m
Deal found 9/7![Delta logo]()
$343
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 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.
Mon 11/96:00 am -
1 stop6h 15m
Fri 11/138:25 am -
2 stops11h 09m
Deal found 9/5![United Airlines logo]()
$336
This JetBlue deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/255:30 am -
1 stop7h 13m
Thu 10/292:13 pm -
Nonstop4h 46m
Deal found 9/9![JetBlue logo]()
$462
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:37 pm -
1 stop9h 17m
Tue 11/242:50 pm -
Nonstop4h 16m
Deal found 9/8![Delta logo]()
$353
This Copa Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/122:50 pm -
1 stop19h 40m
Mon 11/1612:25 pm -
1 stop10h 36m
Deal found 9/9![Copa Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/69:51 am -
1 stop12h 55m
Tue 10/136:00 am -
1 stop8h 35m
Deal found 9/8![United Airlines logo]()
$350
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 JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/247:30 am -
1 stop6h 35m
Thu 1/282:00 pm -
1 stop5h 49m
Deal found 9/4![JetBlue logo]()
$480
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:55 am -
Nonstop4h 02m
Sat 9/262:10 pm -
Nonstop4h 13m
Deal found 9/5![Delta logo]()
$370
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/136:00 am -
1 stop7h 45m
Mon 10/193:56 pm -
1 stop8h 58m
Deal found 9/8![United Airlines logo]()
$356
This JetBlue deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/2511:04 am -
Nonstop4h 56m
Sun 11/15:00 pm -
Nonstop5h 09m
Deal found 9/9![JetBlue logo]()
$492
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/316:25 am -
Nonstop4h 55m
Sun 2/146:00 pm -
Nonstop5h 10m
Deal found 9/8![Delta logo]()
$393
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.
Wed 1/2710:41 am -
1 stop7h 26m
Wed 2/34:45 pm -
1 stop8h 12m
Deal found 9/5![JetBlue logo]()
$497
This United Airlines deal was found by Cheapflights users on 9/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:13 pm -
2 stops17h 37m
Tue 10/271:52 pm -
1 stop17h 51m
Deal found 9/6![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 2/410:45 am -
Nonstop5h 00m
Mon 2/86:00 pm -
Nonstop5h 10m
Deal found 9/7![Delta logo]()
$393
Last-minute flights from Boston to CaribbeanDiscover last-minute flight deals from Boston to Caribbean. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean. Data last updated September 10, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2411:17 am -
1 stop22h 18m
Wed 9/3010:42 am -
1 stop23h 40m
Deal found 9/6![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2611:36 am -
1 stop9h 12m
Fri 10/27:15 am -
1 stop26h 14m
Deal found 9/8![Multiple Airlines logo]()
$311
This Super.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/287:55 am -
Nonstop4h 07m
Sun 10/116:20 am -
Nonstop4h 04m
Deal found 9/7![JetBlue logo]()
$317
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1411:10 am -
Nonstop4h 04m
Fri 10/163:00 am -
1 stop8h 02m
Deal found 9/5![Multiple Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:19 am -
1 stop27h 12m
Fri 10/237:00 am -
1 stop26h 29m
Deal found 9/9![Multiple Airlines logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:19 am -
1 stop11h 36m
Sat 10/313:47 pm -
1 stop20h 57m
Deal found 9/7![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:19 am -
1 stop11h 36m
Wed 10/216:42 pm -
1 stop16h 20m
Deal found 9/8![Multiple Airlines logo]()
$314
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:42 pm -
Nonstop4h 07m
Fri 10/237:35 pm -
Nonstop4h 08m
Deal found 9/5![JetBlue logo]()
$318
This Booking.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Thu 10/2210:20 pm -
Nonstop4h 15m
Thu 10/294:29 pm -
Nonstop4h 21m
Deal found 9/7![Arajet logo]()
$339
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.
Sat 10/247:13 pm -
2 stops17h 37m
Sat 10/314:00 pm -
1 stop7h 59m
Deal found 9/5![United Airlines logo]()
$305
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.
Sat 10/247:13 pm -
2 stops17h 37m
Wed 10/281:52 pm -
2 stops19h 31m
Deal found 9/5![United Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:19 am -
1 stop27h 06m
Fri 11/67:00 am -
1 stop27h 29m
Deal found 9/8![Multiple Airlines logo]()
$303
One-way flights from Boston to CaribbeanSearch for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
Search for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This JetBlue deal was found by Cheapflights users on 9/6. 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.
Sun 12/67:10 am -
1 stop7h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![JetBlue logo]()
$108
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:04 pm -
1 stop18h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Delta logo]()
$113
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 American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:30 am -
1 stop13h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![American Airlines logo]()
$123
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/303:30 pm -
1 stop22h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Air Canada logo]()
$128
This Orbitz deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:40 pm -
2 stops17h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Air Canada logo]()
$128
This Gotogate deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Thu 10/15:50 am -
2 stops11h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Air Canada logo]()
$130
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.
Sun 11/155:00 am -
1 stop16h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$130
This JetBlue deal was found by Cheapflights users on 9/6. 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.
Sat 10/37:11 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![JetBlue logo]()
$131
This Air Canada deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/10![Air Canada logo]()
$133
This Flysmarter deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2511:04 am -
Nonstop4h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![JetBlue logo]()
$134
This Travelocity deal was found by Cheapflights users on 9/6. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:40 pm -
2 stops41h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Air Canada logo]()
$134
Find flight deals from Boston to Caribbean
Keep the following information in mind while searching for Boston to Caribbean flight deals. Data was last updated September 10, 2026.
Round-trip from | $278 (Kiwi.com) |
|---|---|
One-way from | $108 (JetBlue) |
Popular in | July |
Cheapest in | January |
Average price | $316 |
Good round-trip deal | $326 or less |
Good one-way deal | $187 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 10, 2026.
Use the filters below to find and compare flights from Boston to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sun 12/6
8:33 pm-1:50 pm
1 stop16h 17m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sun 12/6
7:10 am-3:11 pm
1 stop7h 01m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sat 12/5
6:00 am-3:57 pm
1 stop8h 57m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Tue 12/8
5:45 am-12:55 pm
1 stop6h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Fri 12/4
8:25 pm-3:57 pm
1 stop18h 32m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Mon 12/7
5:45 am-12:55 pm
1 stop6h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Tue 12/8
5:20 am-2:40 pm
1 stop8h 20m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Mon 12/7
7:04 pm-2:40 pm
1 stop18h 36m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Thu 10/8
5:50 am-1:25 pm
1 stop7h 35m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$128
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Wed 10/14
6:00 am-1:07 pm
2 stops7h 07m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Boston to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Boston with our price prediction graph.
BOS-SJU
BOS-SXM
BOS-NAS
BOS-AUA
BOS-SDQ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Boston to Caribbean
BOS-0CB
BOS-SJU
BOS-SXM
BOS-NAS
BOS-AUA
What is the cheapest month to book a flight from Boston to Caribbean?
Currently, March is the cheapest month in which you can book a flight from Boston to Caribbean (average of $428). Flying from Boston to Caribbean in December is currently the most expensive (average of $604). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from BOS to CB?
Find hourly flight availability from Boston to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 10, 2026.
It’s typically best to fly out from Boston to Caribbean in the afternoon. Doing so could potentially save you 21% on the flight price compared to flying at noon, which is usually more expensive.
Weekly flight availability from Boston to Caribbean
Explore weekly flight availability from Boston to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 10, 2026.
The most flights from BOS to 0CB are scheduled on a Wednesday (5 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?
The best time to book flights from Boston to Caribbean is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Boston to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Boston to Caribbean. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Boston to Caribbean 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
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated September 10, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Boston to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Entertainment
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Related info for your journey
Find useful and relevant information for your journey from Boston to Caribbean. 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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Boston to Caribbean by cabin class
Find flights from Boston to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Boston and Caribbean flights
Browse other Boston and Caribbean flight options. Last updated on September 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Boston to Caribbean flights
Consider these flights traveling from Boston to Caribbean.
Top 9 airlines flying from Boston to Caribbean
Discover the top 9 airlines that operate flights from Boston to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$451 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$141 | Average$617 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$161 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$166 | Average$477 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$173 | Average$540 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$183 | Average$388 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$187 | Average$410 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$590 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$537 | FlexibilityNo cancel fee | On-timeN/A |