$117+ Cheap flights from Virginia to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Sep 19 — Sep 261
Round-trip
1 adult, Economy
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Find cheap flights from Virginia 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 Virginia to Caribbean
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Cheapest flights from Virginia to CaribbeanExplore the most affordable flight options available from Virginia to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2026.
Explore the most affordable flight options available from Virginia to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2026.
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:15 pm -
Nonstop3h 44m
Thu 9/33:28 pm -
Nonstop3h 52m
Deal found 8/19![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/1610:07 am -
1 stop7h 36m
Wed 9/236:42 pm -
1 stop14h 27m
Deal found 8/19![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/83:47 pm -
1 stop23h 30m
Sat 9/129:30 am -
1 stop23h 29m
Deal found 8/17![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/3010:07 am -
1 stop7h 36m
Mon 10/57:00 am -
1 stop6h 59m
Deal found 8/19![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 8/308:15 pm -
Nonstop3h 44m
Fri 9/187:02 pm -
1 stop14h 38m
Deal found 8/18![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 8/308:15 pm -
Nonstop3h 44m
Mon 9/2112:59 am -
1 stop10h 07m
Deal found 8/18![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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.
Sun 9/68:15 pm -
Nonstop3h 44m
Sat 9/129:30 am -
1 stop23h 29m
Deal found 8/17![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 10/110:35 am -
1 stop26h 59m
Thu 10/87:00 am -
1 stop6h 59m
Deal found 8/18![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/912:05 pm -
1 stop29h 43m
Mon 9/146:55 pm -
1 stop16h 11m
Deal found 8/17![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 9/68:15 pm -
Nonstop3h 44m
Tue 9/2212:59 am -
1 stop10h 07m
Deal found 8/18![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Mon 10/1210:05 am -
1 stop29h 13m
Mon 10/197:00 am -
1 stop6h 59m
Deal found 8/19![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 8/308:15 pm -
Nonstop3h 44m
Thu 9/244:39 pm -
1 stop23h 15m
Deal found 8/18![Frontier logo]()
$232
Best flights from Virginia to CaribbeanDiscover carefully curated flight deals from Virginia to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
Discover carefully curated flight deals from Virginia to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 20, 2026.
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/86:30 am -
1 stop8h 10m
Sat 11/147:40 am -
1 stop9h 08m
Deal found 8/17![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/88:40 am -
1 stop8h 09m
Fri 11/136:35 pm -
1 stop6h 51m
Deal found 8/17![Delta logo]()
$298
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/26:00 am -
1 stop6h 20m
Sun 9/65:20 am -
2 stops9h 20m
Deal found 8/17![Southwest logo]()
$315
This JetBlue deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 11/181:20 pm -
1 stop10h 05m
Tue 11/247:00 pm -
Nonstop3h 58m
Deal found 8/15![JetBlue logo]()
$337
This Copa Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/82:25 am -
1 stop16h 12m
Fri 10/161:19 pm -
1 stop15h 01m
Deal found 8/17![Copa Airlines logo]()
$496
This Air Canada deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/146:59 am -
1 stop8h 26m
Sat 9/195:05 pm -
2 stops19h 09m
Deal found 8/15![Air Canada logo]()
$503
This American Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/25:00 am -
2 stops10h 19m
Sat 9/512:10 pm -
1 stop8h 51m
Deal found 8/15![American Airlines logo]()
$565
This United deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/58:56 am -
Nonstop4h 00m
Tue 11/1010:49 am -
1 stop25h 20m
Deal found 8/19![Multiple Airlines logo]()
$635
This Delta deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 1/192:30 pm -
1 stop8h 20m
Sat 1/306:15 am -
1 stop7h 34m
Deal found 8/18![Delta logo]()
$336
This JetBlue deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 11/168:00 am -
Nonstop3h 51m
Mon 11/237:00 pm -
Nonstop3h 58m
Deal found 8/15![JetBlue logo]()
$342
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/201:15 pm -
2 stops8h 35m
Mon 10/266:00 am -
1 stop6h 25m
Deal found 8/16![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/258:40 am -
Nonstop3h 54m
Tue 9/291:25 pm -
1 stop8h 02m
Deal found 8/19![United Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 1/305:20 am -
1 stop6h 45m
Sat 2/66:15 am -
1 stop7h 34m
Deal found 8/16![Delta logo]()
$336
This JetBlue deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 2/1612:15 pm -
1 stop7h 34m
Tue 3/26:49 pm -
Nonstop4h 10m
Deal found 8/16![JetBlue logo]()
$347
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/92:40 pm -
1 stop8h 25m
Tue 10/138:15 am -
1 stop6h 45m
Deal found 8/17![Southwest logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/156:25 am -
1 stop8h 19m
Tue 9/221:00 am -
1 stop7h 57m
Deal found 8/15![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 9/101:00 pm -
2 stops9h 15m
Thu 9/176:30 am -
2 stops8h 15m
Deal found 8/15![Southwest logo]()
$375
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 11/1812:35 pm -
1 stop10h 20m
Thu 11/267:15 am -
1 stop11h 13m
Deal found 8/15![Delta logo]()
$386
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 12/26:00 am -
1 stop6h 15m
Sun 12/64:52 pm -
1 stop8h 22m
Deal found 8/16![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 1/116:00 am -
1 stop7h 31m
Fri 1/227:00 am -
1 stop11h 30m
Deal found 8/19![Delta logo]()
$386
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/163:25 pm -
2 stops9h 55m
Mon 10/195:00 am -
2 stops7h 55m
Deal found 8/19![Southwest logo]()
$386
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 11/168:22 am -
Nonstop3h 53m
Mon 11/238:05 am -
Nonstop4h 04m
Deal found 8/19![United Airlines logo]()
$402
This JetBlue deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 11/36:00 am -
1 stop6h 43m
Fri 11/62:00 pm -
1 stop6h 59m
Deal found 8/15![JetBlue logo]()
$458
This Delta deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 11/186:04 am -
1 stop10h 16m
Mon 11/237:15 am -
1 stop10h 22m
Deal found 8/15![Delta logo]()
$386
This Copa Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 2/111:19 am -
1 stop9h 56m
Tue 2/162:28 pm -
1 stop12h 48m
Deal found 8/19![Copa Airlines logo]()
$575
This Southwest deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Mon 9/142:40 pm -
2 stops9h 15m
Thu 9/176:30 am -
2 stops9h 40m
Deal found 8/19![Southwest logo]()
$394
This United Airlines deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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 9/268:25 am -
2 stops12h 13m
Sat 10/31:00 am -
2 stops11h 08m
Deal found 8/18![United Airlines logo]()
$413
This JetBlue deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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 10/286:00 am -
1 stop7h 08m
Mon 11/211:30 am -
1 stop11h 18m
Deal found 8/15![JetBlue logo]()
$466
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/26:00 am -
2 stops10h 25m
Sun 9/65:20 am -
2 stops11h 25m
Deal found 8/17![Southwest logo]()
$396
This United deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/16:00 am -
1 stop9h 20m
Tue 11/101:46 pm -
1 stop22h 23m
Deal found 8/19![Multiple Airlines logo]()
$639
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated August 20, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated August 20, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:15 pm -
Nonstop3h 44m
Thu 9/33:28 pm -
Nonstop3h 52m
Deal found 8/19![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 8/308:15 pm -
Nonstop3h 44m
Fri 9/187:02 pm -
1 stop14h 38m
Deal found 8/18![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 8/308:15 pm -
Nonstop3h 44m
Mon 9/2112:59 am -
1 stop10h 07m
Deal found 8/18![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 8/308:15 pm -
Nonstop3h 44m
Thu 9/244:39 pm -
1 stop23h 15m
Deal found 8/18![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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.
Sun 9/68:15 pm -
Nonstop3h 44m
Sat 9/129:30 am -
1 stop23h 29m
Deal found 8/17![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 9/68:15 pm -
Nonstop3h 44m
Thu 9/102:57 am -
1 stop6h 21m
Deal found 8/18![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sun 9/68:15 pm -
Nonstop3h 44m
Tue 9/2212:59 am -
1 stop10h 07m
Deal found 8/18![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/83:47 pm -
1 stop23h 30m
Sat 9/129:30 am -
1 stop23h 29m
Deal found 8/17![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/912:05 pm -
1 stop29h 43m
Mon 9/146:55 pm -
1 stop16h 11m
Deal found 8/17![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Fri 9/119:35 pm -
1 stop12h 00m
Mon 9/142:57 am -
1 stop13h 34m
Deal found 8/19![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/1610:07 am -
1 stop7h 36m
Wed 9/236:42 pm -
1 stop14h 27m
Deal found 8/19![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/3010:07 am -
1 stop7h 36m
Mon 10/57:00 am -
1 stop6h 59m
Deal found 8/19![Frontier logo]()
$224
One-way flights from Virginia to CaribbeanSearch for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/1512:05 pm -
1 stop22h 08m
Deal found 8/17![Frontier logo]()
$117
This eDestinos deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:46 pm -
1 stop11h 49m
Deal found 8/18![Multiple Airlines logo]()
$118
This Faresmojo deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:35 pm -
1 stop6h 54m
Deal found 8/16![JetBlue logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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.
Fri 9/114:49 pm -
1 stop24h 01m
Deal found 8/15![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Mon 9/1410:35 am -
1 stop28h 42m
Deal found 8/16![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/249:46 pm -
1 stop16h 32m
Deal found 8/19![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/171:27 pm -
2 stops10h 11m
Deal found 8/17![Multiple Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/205:26 pm -
1 stop8h 27m
Deal found 8/19![Frontier logo]()
$126
This Faresmojo deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
1 stop7h 42m
Deal found 8/17![JetBlue logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” 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.
Sun 10/1110:42 am -
2 stops26h 49m
Deal found 8/15![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/1910:35 am -
1 stop26h 59m
Deal found 8/17![Frontier logo]()
$129
This Frontier deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” 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.
Sat 8/297:00 am -
1 stop6h 17m
Deal found 8/18![Frontier logo]()
$134
Find flight deals from Virginia to Caribbean
Keep the following information in mind while searching for Virginia to Caribbean flight deals. Data was last updated August 20, 2026.
Round-trip from | $221 (Kiwi.com) |
|---|---|
One-way from | $117 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $353 |
Good round-trip deal | $290 or less |
Good one-way deal | $134 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Virginia 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 August 20, 2026.
Use the filters below to find and compare flights from Virginia to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sun 11/8
6:30 am-3:40 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Sat 11/14
7:40 am-3:48 pm
1 stop9h 08m
$292
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sun 11/8
8:40 am-5:49 pm
1 stop8h 09m
San Juan Luis Munoz Marin Intl
Fri 11/13
6:35 pm-12:26 am
1 stop6h 51m
$298
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Wed 9/2
6:00 am-12:20 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Sun 9/6
5:20 am-2:40 pm
2 stops9h 20m
$315
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Tue 1/19
2:30 pm-11:50 pm
1 stop8h 20m
San Juan Luis Munoz Marin Intl
Sat 1/30
6:15 am-12:49 pm
1 stop7h 34m
$336
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sat 1/30
5:20 am-1:05 pm
1 stop6h 45m
San Juan Luis Munoz Marin Intl
Sat 2/6
6:15 am-12:49 pm
1 stop7h 34m
$336
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Wed 11/18
1:20 pm-12:25 am
1 stop10h 05m
San Juan Luis Munoz Marin Intl
Tue 11/24
7:00 pm-9:58 pm
Nonstop3h 58m
$337
Quickest round-trip
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Mon 11/16
8:00 am-12:51 pm
Nonstop3h 51m
San Juan Luis Munoz Marin Intl
Mon 11/23
7:00 pm-9:58 pm
Nonstop3h 58m
$342
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Tue 2/16
12:15 pm-8:49 pm
1 stop7h 34m
San Juan Luis Munoz Marin Intl
Tue 3/2
6:49 pm-9:59 pm
Nonstop4h 10m
$347
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Tue 10/20
1:15 pm-9:50 pm
2 stops8h 35m
San Juan Luis Munoz Marin Intl
Mon 10/26
6:00 am-12:25 pm
1 stop6h 25m
$355
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Fri 10/9
2:40 pm-11:05 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Tue 10/13
8:15 am-3:00 pm
1 stop6h 45m
$355
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Virginia to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Virginia with our price prediction graph.
RDU-SJU
DCA-SJU
IAD-AUA
DCA-PUJ
IAD-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 Virginia to Caribbean
USVA-0CB
RDU-SJU
DCA-SJU
IAD-AUA
DCA-PUJ
What is the cheapest month to book a flight from Virginia to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $448). Flying from Virginia to Caribbean in December is currently the most expensive (average of $621). 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 VA to CB?
Find hourly flight availability from Virginia 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 August 20, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia to Caribbean as you normally would.
How far ahead should I book a flight from Virginia to Caribbean?
The price you pay for your flight from Virginia to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Related info for your journey
Find useful and relevant information for your journey from Virginia to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Virginia 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 Virginia to Caribbean by cabin class
Find flights from Virginia to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Virginia and Caribbean flights
Browse other Virginia and Caribbean flight options. Last updated on August 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean
Find the right flight back to Virginia after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Virginia to Caribbean flights
Consider these flights traveling from Virginia to Caribbean.
Top 7 airlines flying from Virginia to Caribbean
Discover the top 7 airlines that operate flights from Virginia 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 August 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$379 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$107 | Average$534 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$212 | Average$593 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$219 | Average$535 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$237 | Average$618 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |