$94+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SJU
Nov 25 — Dec 21
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
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
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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 October 26, 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 October 26, 2026.
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/96:05 am -
1 stop9h 51m
Fri 11/132:10 pm -
1 stop9h 45m
Deal found 10/21![Delta logo]()
$290
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/96:00 am -
1 stop6h 51m
Wed 11/181:53 pm -
1 stop7h 24m
Deal found 10/21![American Airlines logo]()
$291
This Jetabroad deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:30 pm -
1 stop6h 22m
Tue 12/82:04 pm -
1 stop8h 28m
Deal found 10/23![JetBlue logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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.
Thu 12/1011:34 am -
1 stop12h 33m
Wed 12/236:11 am -
Nonstop4h 19m
Deal found 10/22![Frontier logo]()
$293
This Frontier deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:06 am -
1 stop14h 18m
Wed 12/236:11 am -
Nonstop4h 19m
Deal found 10/22![Frontier logo]()
$294
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/91:00 pm -
1 stop6h 48m
Fri 11/137:00 am -
Nonstop4h 13m
Deal found 10/21![JetBlue logo]()
$295
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/154:09 pm -
1 stop7h 21m
Tue 11/177:00 am -
Nonstop4h 13m
Deal found 10/22![JetBlue logo]()
$296
This CheapOair deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Wed 11/1812:39 pm -
1 stop11h 20m
Wed 12/27:00 am -
Nonstop4h 14m
Deal found 10/21![Multiple Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/912:00 pm -
2 stops9h 22m
Fri 11/132:05 am -
1 stop6h 38m
Deal found 10/22![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/98:09 am -
2 stops8h 56m
Fri 11/137:30 am -
1 stop7h 40m
Deal found 10/21![American Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Thu 12/311:57 am -
1 stop12h 10m
Wed 12/96:25 am -
1 stop28h 14m
Deal found 10/21![Multiple Airlines logo]()
$303
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/295:30 am -
1 stop6h 25m
Thu 12/33:30 pm -
1 stop9h 18m
Deal found 10/21![JetBlue logo]()
$347
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 October 26, 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 October 26, 2026.
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/154:09 pm -
1 stop7h 21m
Tue 11/177:00 am -
Nonstop4h 13m
Deal found 10/22![JetBlue logo]()
$296
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/158:40 am -
Nonstop4h 03m
Wed 11/182:55 pm -
Nonstop4h 16m
Deal found 10/21![Delta logo]()
$306
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/76:00 am -
1 stop8h 57m
Sat 11/142:10 pm -
2 stops18h 33m
Deal found 10/22![United Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/53:05 pm -
1 stop6h 50m
Fri 12/116:35 am -
1 stop6h 40m
Deal found 10/23![Southwest logo]()
$407
This Copa Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/252:50 pm -
1 stop22h 51m
Sat 12/51:14 pm -
1 stop25h 09m
Deal found 10/21![Copa Airlines logo]()
$431
This Arajet deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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.
Sun 11/89:20 pm -
Nonstop4h 22m
Fri 11/206:24 am -
Nonstop4h 21m
Deal found 10/22![Arajet logo]()
$446
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/297:00 am -
Nonstop4h 08m
Sat 12/57:00 am -
Nonstop4h 14m
Deal found 10/21![JetBlue logo]()
$327
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/306:39 pm -
2 stops18h 11m
Sat 2/135:00 pm -
1 stop7h 59m
Deal found 10/24![United Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/1910:45 am -
Nonstop5h 00m
Tue 2/24:35 pm -
1 stop9h 23m
Deal found 10/21![Delta logo]()
$405
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/26:30 pm -
1 stop6h 22m
Sun 12/67:00 am -
Nonstop4h 16m
Deal found 10/21![JetBlue logo]()
$393
This Southwest deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/225:45 am -
1 stop6h 35m
Sat 1/303:20 pm -
1 stop8h 25m
Deal found 10/25![Southwest logo]()
$435
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/136:00 am -
1 stop8h 06m
Thu 11/196:00 am -
1 stop10h 50m
Deal found 10/23![United Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/110:52 am -
Nonstop4h 53m
Mon 1/116:00 pm -
Nonstop5h 10m
Deal found 10/23![Delta logo]()
$415
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/305:01 am -
Nonstop4h 01m
Mon 12/71:55 pm -
1 stop6h 55m
Deal found 10/21![JetBlue logo]()
$404
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/612:26 pm -
2 stops24h 24m
Wed 1/132:52 pm -
2 stops20h 33m
Deal found 10/21![United Airlines logo]()
$411
This Copa Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Tue 11/172:50 pm -
1 stop20h 28m
Tue 12/112:18 pm -
1 stop25h 05m
Deal found 10/21![Copa Airlines logo]()
$520
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/1810:59 pm -
Nonstop4h 06m
Wed 12/212:42 pm -
1 stop12h 06m
Deal found 10/22![JetBlue logo]()
$407
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/66:05 am -
1 stop10h 12m
Sat 2/135:35 pm -
Nonstop4h 20m
Deal found 10/24![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/218:00 pm -
1 stop16h 50m
Sun 1/245:00 pm -
1 stop7h 59m
Deal found 10/21![United Airlines logo]()
$413
This JetBlue deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/279:50 pm -
Nonstop4h 07m
Tue 12/112:42 pm -
1 stop12h 06m
Deal found 10/23![JetBlue logo]()
$410
This Copa Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/242:50 pm -
1 stop20h 28m
Tue 12/112:18 pm -
1 stop9h 51m
Deal found 10/24![Copa Airlines logo]()
$554
This Delta deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/78:05 am -
Nonstop4h 08m
Sun 2/144:15 pm -
1 stop9h 43m
Deal found 10/25![Delta logo]()
$461
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/86:00 am -
2 stops10h 50m
Sat 1/165:25 pm -
1 stop7h 34m
Deal found 10/22![United Airlines logo]()
$420
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/68:10 am -
1 stop5h 55m
Sat 1/163:15 pm -
1 stop8h 33m
Deal found 10/22![JetBlue logo]()
$413
This Delta deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/189:25 am -
Nonstop3h 45m
Sat 1/232:40 pm -
Nonstop3h 30m
Deal found 10/22![Delta logo]()
$462
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/168:25 pm -
1 stop18h 32m
Tue 12/222:52 pm -
1 stop8h 58m
Deal found 10/21![United Airlines logo]()
$430
This JetBlue deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:25 am -
Nonstop4h 09m
Wed 1/132:15 pm -
1 stop8h 36m
Deal found 10/25![JetBlue logo]()
$413
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/119:25 am -
Nonstop3h 45m
Fri 1/152:40 pm -
Nonstop3h 30m
Deal found 10/21![Delta logo]()
$462
This United Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/205:45 am -
2 stops33h 12m
Tue 12/292:52 pm -
1 stop8h 58m
Deal found 10/25![United Airlines logo]()
$431
This JetBlue deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/196:10 pm -
1 stop7h 18m
Sun 11/223:55 am -
Nonstop4h 14m
Deal found 10/23![JetBlue logo]()
$415
Last-minute flights from Boston to CaribbeanDiscover last-minute flight deals from Boston to Caribbean. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Boston to Caribbean. Data last updated October 26, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/86:00 am -
1 stop14h 29m
Fri 11/137:05 am -
1 stop7h 44m
Deal found 10/21![American Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/96:05 am -
1 stop9h 51m
Fri 11/132:10 pm -
1 stop9h 45m
Deal found 10/21![Delta logo]()
$290
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/96:00 am -
1 stop6h 51m
Wed 11/181:53 pm -
1 stop7h 24m
Deal found 10/21![American Airlines logo]()
$291
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/91:00 pm -
1 stop6h 48m
Fri 11/137:00 am -
Nonstop4h 13m
Deal found 10/21![JetBlue logo]()
$295
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/912:00 pm -
2 stops9h 22m
Fri 11/132:05 am -
1 stop6h 38m
Deal found 10/22![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/98:09 am -
2 stops8h 56m
Fri 11/137:30 am -
1 stop7h 40m
Deal found 10/21![American Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/106:00 am -
1 stop6h 32m
Tue 11/105:50 pm -
1 stop7h 09m
Deal found 10/22![United Airlines logo]()
$305
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/154:09 pm -
1 stop7h 21m
Tue 11/177:00 am -
Nonstop4h 13m
Deal found 10/22![JetBlue logo]()
$296
This CheapOair deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Wed 11/1812:39 pm -
1 stop11h 20m
Wed 12/27:00 am -
Nonstop4h 14m
Deal found 10/21![Multiple Airlines logo]()
$299
This Frontier deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:06 am -
1 stop14h 18m
Wed 12/236:11 am -
Nonstop4h 19m
Deal found 10/22![Frontier logo]()
$294
This Justfly.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2611:06 am -
1 stop14h 18m
Fri 12/42:45 pm -
Nonstop4h 16m
Deal found 10/21![Multiple Airlines logo]()
$304
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/295:30 am -
1 stop6h 25m
Thu 12/33:30 pm -
1 stop9h 18m
Deal found 10/21![JetBlue logo]()
$347
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 October 26, 2026.
Search for one-way flight options from Boston to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/118:25 pm -
1 stop18h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$94
This JetBlue deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/175:30 am -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![JetBlue logo]()
$98
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/295:45 am -
1 stop9h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![United Airlines logo]()
$108
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/36:38 pm -
2 stops17h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$110
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/316:30 am -
1 stop7h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![JetBlue logo]()
$115
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/176:00 am -
2 stops9h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$119
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/27:15 pm -
2 stops17h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![United Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 10/22![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/75:30 pm -
2 stops19h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$122
This United Airlines deal was found by Cheapflights users on 10/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop8h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![United Airlines logo]()
$125
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/305:27 am -
1 stop6h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$126
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 1/35:35 pm -
1 stop18h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$135
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 October 26, 2026.
Round-trip from | $290 (Delta) |
|---|---|
One-way from | $98 (JetBlue) |
Popular in | July |
Cheapest in | January |
Average price | $354 |
Good round-trip deal | $400 or less |
Good one-way deal | $200 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 October 26, 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
Tue 11/17
5:30 am-2:30 pm
1 stop8h 00m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$98
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Mon 12/28
7:40 pm-3:57 pm
2 stops19h 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
Wed 12/30
7:40 pm-1:50 pm
2 stops17h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$110
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sat 1/30
8:45 pm-12:15 pm
1 stop14h 30m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$120
BostonSimpson Bay
BOS Boston Logan Intl - SXM Simpson Bay Princess Juliana
BOSSXM
Boston Logan Intl
Sat 2/6
6:00 am-3:57 pm
1 stop8h 57m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Sat 12/5
5:45 am-12:55 pm
1 stop7h 10m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$131
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Sun 1/3
5:30 am-11:21 am
1 stop5h 51m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$131
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Mon 1/4
7:30 am-3:56 pm
1 stop8h 26m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$131
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Wed 1/13
5:00 am-11:17 am
1 stop6h 17m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$136
BostonNassau
BOS Boston Logan Intl - NAS Nassau Intl
BOSNAS
Boston Logan Intl
Tue 12/15
7:00 am-5:50 pm
2 stops10h 50m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$138
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-AUA
BOS-SDQ
BOS-STT
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-AUA
BOS-SDQ
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 $435). Flying from Boston to Caribbean in December is currently the most expensive (average of $618). 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 October 26, 2026.
It’s typically best to fly out from Boston to Caribbean in the afternoon. Doing so could potentially save you 17% on the flight price compared to flying at noon, which is usually more expensive.
How often are flights from Boston to Caribbean delayed?
About 28% of weekly flights between Boston and Caribbean have experienced delays in the past year, with the average delay time being 149 minutes.
What is the most punctual flight time for Boston to Caribbean flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Boston to Caribbean flights?
Over the last year, Delta have had the lowest number of delays on this route, with just 17% of flights being delayed.
How far ahead should I book a flight from Boston to Caribbean?
The best time to book flights from Boston to Caribbean is 51 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 October 17, 2026.
Travelers seeking maximum savings on their Boston to Caribbean flight should consider departing on Sunday at noon when fares are most often at their lowest. Thursday mornings 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 October 26, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue from Boston to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
6.0
GoodCidalia,Aug 2023
BOS - MIA
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Comfort
7.8
Crew
8.5
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 October 26, 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 October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$409 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$622 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$166 | Average$485 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$168 | Average$499 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$183 | Average$472 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$183 | Average$540 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$397 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$259 | Average$586 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$506 | FlexibilityNo cancel fee | On-timeN/A |