$98+ Cheap flights from Virginia 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 12 — Dec 191
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 November 12, 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 November 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:59 pm -
1 stop8h 29m
Tue 12/84:04 pm -
1 stop22h 00m
Deal found 11/10![Frontier logo]()
$242
This JetBlue deal was found by Cheapflights users on 11/9. 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 12/64:24 pm -
1 stop8h 10m
Thu 12/107:45 am -
Nonstop3h 42m
Deal found 11/9![JetBlue logo]()
$245
This FlightHub deal was found by Cheapflights users on 11/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:50 pm -
Nonstop3h 39m
Tue 12/111:48 am -
1 stop26h 12m
Deal found 11/9![Multiple Airlines logo]()
$247
This Frontier deal was found by Cheapflights users on 11/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:53 pm -
1 stop9h 53m
Wed 11/183:55 am -
1 stop12h 03m
Deal found 11/8![Frontier logo]()
$249
This JetBlue deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 11/266:00 am -
1 stop7h 34m
Thu 12/38:00 am -
1 stop8h 39m
Deal found 11/11![JetBlue logo]()
$253
This JetBlue deal was found by Cheapflights users on 11/8. 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.
Sat 12/124:34 pm -
1 stop8h 00m
Sun 12/204:28 pm -
1 stop6h 13m
Deal found 11/8![JetBlue logo]()
$254
This Frontier deal was found by Cheapflights users on 11/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:53 pm -
1 stop9h 53m
Mon 11/237:17 am -
1 stop8h 17m
Deal found 11/10![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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.
Thu 11/193:53 pm -
1 stop9h 53m
Sun 11/2210:21 pm -
1 stop17h 13m
Deal found 11/12![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:59 pm -
1 stop8h 29m
Sat 12/53:27 pm -
1 stop18h 19m
Deal found 11/10![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/55:09 pm -
1 stop8h 04m
Mon 12/1411:00 am -
1 stop22h 53m
Deal found 11/11![Multiple Airlines logo]()
$259
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/111:20 am -
Nonstop3h 42m
Tue 12/87:45 am -
Nonstop3h 42m
Deal found 11/7![JetBlue logo]()
$260
This Cheapflightsfares deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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.
Thu 11/123:53 pm -
1 stop25h 28m
Sat 11/147:26 pm -
1 stop20h 32m
Deal found 11/11![Frontier logo]()
$261
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 November 12, 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 November 12, 2026.
This JetBlue deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 12/155:59 pm -
1 stop7h 06m
Thu 12/1710:00 am -
1 stop7h 53m
Deal found 11/12![JetBlue logo]()
$253
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 1/256:15 am -
2 stops13h 45m
Thu 1/288:25 am -
2 stops12h 50m
Deal found 11/11![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 11/9. 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.
Mon 1/116:13 am -
2 stops9h 36m
Thu 1/144:19 pm -
2 stops19h 10m
Deal found 11/9![American Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 1/214:59 pm -
1 stop6h 59m
Sun 1/247:17 am -
1 stop9h 59m
Deal found 11/12![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/103:05 pm -
2 stops8h 45m
Thu 12/1712:40 pm -
2 stops10h 30m
Deal found 11/11![Southwest logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Fri 12/115:09 pm -
2 stops20h 22m
Wed 12/1611:35 am -
1 stop11h 54m
Deal found 11/9![Multiple Airlines logo]()
$533
This JetBlue deal was found by Cheapflights users on 11/9. 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.
Thu 11/2612:50 pm -
Nonstop3h 39m
Wed 12/210:00 am -
1 stop6h 44m
Deal found 11/9![JetBlue logo]()
$292
This JetBlue deal was found by Cheapflights users on 11/9. 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.
Thu 11/2612:50 pm -
Nonstop3h 39m
Tue 12/17:45 am -
Nonstop3h 42m
Deal found 11/9![JetBlue logo]()
$292
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/206:20 am -
2 stops14h 04m
Wed 1/278:05 am -
2 stops9h 29m
Deal found 11/9![United Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 12/156:13 am -
1 stop6h 46m
Tue 12/224:15 pm -
1 stop8h 43m
Deal found 11/12![American Airlines logo]()
$342
This Copa Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 4/276:00 am -
2 stops20h 15m
Tue 5/412:44 pm -
2 stops20h 51m
Deal found 11/11![Copa Airlines logo]()
$687
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/97:00 am -
1 stop8h 36m
Wed 12/163:15 pm -
1 stop7h 20m
Deal found 11/11![Delta logo]()
$366
This JetBlue deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 1/2812:40 pm -
Nonstop3h 29m
Sat 1/302:15 pm -
1 stop9h 09m
Deal found 11/11![JetBlue logo]()
$303
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/246:15 am -
1 stop9h 25m
Tue 3/25:35 pm -
1 stop6h 39m
Deal found 11/10![United Airlines logo]()
$342
This JetBlue deal was found by Cheapflights users on 11/9. 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.
Fri 12/44:34 pm -
1 stop8h 00m
Sat 12/128:50 am -
Nonstop3h 42m
Deal found 11/9![JetBlue logo]()
$306
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 11/305:30 am -
1 stop8h 20m
Sat 12/53:15 pm -
1 stop9h 43m
Deal found 11/11![Delta logo]()
$387
This Southwest deal was found by Cheapflights users on 11/9. 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 12/103:05 pm -
2 stops8h 45m
Sun 12/136:05 am -
2 stops9h 40m
Deal found 11/9![Southwest logo]()
$428
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/246:15 am -
1 stop9h 25m
Mon 3/13:00 pm -
1 stop20h 12m
Deal found 11/10![United Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 11/10. 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.
Mon 11/301:39 pm -
2 stops8h 15m
Sat 12/511:51 am -
1 stop10h 17m
Deal found 11/10![American Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 11/9. 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.
Fri 1/812:35 pm -
2 stops11h 05m
Sat 1/165:35 am -
2 stops10h 55m
Deal found 11/9![Southwest logo]()
$428
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/286:20 am -
2 stops8h 07m
Wed 2/312:55 pm -
1 stop10h 04m
Deal found 11/9![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 1/245:20 am -
1 stop5h 54m
Fri 1/296:09 pm -
1 stop6h 17m
Deal found 11/11![Delta logo]()
$404
This JetBlue deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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 2/612:40 pm -
Nonstop3h 29m
Tue 2/910:00 am -
1 stop6h 48m
Deal found 11/12![JetBlue logo]()
$336
This American Airlines deal was found by Cheapflights users on 11/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/106:10 am -
2 stops8h 25m
Fri 1/156:05 pm -
2 stops16h 24m
Deal found 11/7![American Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/225:30 am -
1 stop6h 19m
Mon 12/281:05 pm -
1 stop10h 25m
Deal found 11/9![United Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 11/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/245:25 am -
2 stops10h 55m
Mon 3/15:55 pm -
2 stops17h 54m
Deal found 11/8![American Airlines logo]()
$441
This JetBlue deal was found by Cheapflights users on 11/8. 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.
Wed 12/25:59 pm -
1 stop7h 00m
Tue 12/87:45 am -
Nonstop3h 42m
Deal found 11/8![JetBlue logo]()
$365
This United Airlines deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/96:00 am -
1 stop7h 33m
Wed 12/1612:55 pm -
2 stops10h 47m
Deal found 11/11![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 1/318:00 am -
1 stop6h 33m
Thu 2/43:13 pm -
1 stop8h 35m
Deal found 11/11![Delta logo]()
$462
This American Airlines deal was found by Cheapflights users on 11/9. 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.
Thu 1/2110:54 am -
2 stops9h 35m
Sun 1/247:18 am -
1 stop11h 44m
Deal found 11/9![American Airlines logo]()
$468
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated November 12, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated November 12, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 11/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:53 pm -
1 stop9h 53m
Wed 11/183:55 am -
1 stop12h 03m
Deal found 11/8![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 11/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:53 pm -
1 stop9h 53m
Sun 11/157:23 am -
1 stop8h 35m
Deal found 11/10![Frontier logo]()
$261
This Frontier deal was found by Cheapflights users on 11/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:53 pm -
1 stop9h 53m
Mon 11/237:17 am -
1 stop8h 17m
Deal found 11/10![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” 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.
Thu 11/193:53 pm -
1 stop9h 53m
Sun 11/2210:21 pm -
1 stop17h 13m
Deal found 11/12![Frontier logo]()
$258
This FlightHub deal was found by Cheapflights users on 11/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2412:50 pm -
Nonstop3h 39m
Tue 12/111:48 am -
1 stop26h 12m
Deal found 11/9![Multiple Airlines logo]()
$247
This JetBlue deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 11/266:00 am -
1 stop7h 34m
Thu 12/38:00 am -
1 stop8h 39m
Deal found 11/11![JetBlue logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 11/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/111:20 am -
Nonstop3h 42m
Tue 12/87:45 am -
Nonstop3h 42m
Deal found 11/7![JetBlue logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:59 pm -
1 stop8h 29m
Sat 12/53:27 pm -
1 stop18h 19m
Deal found 11/10![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/41:59 pm -
1 stop8h 29m
Tue 12/84:04 pm -
1 stop22h 00m
Deal found 11/10![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/55:09 pm -
1 stop8h 04m
Mon 12/1411:00 am -
1 stop22h 53m
Deal found 11/11![Multiple Airlines logo]()
$259
This JetBlue deal was found by Cheapflights users on 11/9. 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 12/64:24 pm -
1 stop8h 10m
Thu 12/107:45 am -
Nonstop3h 42m
Deal found 11/9![JetBlue logo]()
$245
This JetBlue deal was found by Cheapflights users on 11/8. 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.
Sat 12/124:34 pm -
1 stop8h 00m
Sun 12/204:28 pm -
1 stop6h 13m
Deal found 11/8![JetBlue logo]()
$254
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 November 12, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/7. 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.
Thu 12/315:14 pm -
1 stop8h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Frontier logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/55:09 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$99
This United Airlines deal was found by Cheapflights users on 11/8. 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 12/86:00 am -
2 stops15h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![United Airlines logo]()
$103
This JetBlue deal was found by Cheapflights users on 11/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:34 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/10![JetBlue logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:45 pm -
Nonstop3h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![JetBlue logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 11/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/141:59 pm -
1 stop11h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 11/9. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:45 pm -
Nonstop3h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![JetBlue logo]()
$107
This American Airlines deal was found by Cheapflights users on 11/9. 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.
Mon 11/301:39 pm -
1 stop9h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$108
This Frontier deal was found by Cheapflights users on 11/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/233:29 pm -
1 stop9h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Frontier logo]()
$109
This JetBlue deal was found by Cheapflights users on 11/9. 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.
Mon 11/2312:45 pm -
Nonstop3h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![JetBlue logo]()
$109
This American Airlines deal was found by Cheapflights users on 11/9. 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.
Wed 12/97:16 am -
1 stop15h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![American Airlines logo]()
$113
This Southwest deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” 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 12/313:05 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/11![Southwest logo]()
$117
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 November 12, 2026.
Round-trip from | $242 (Kiwi.com) |
|---|---|
One-way from | $98 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $389 |
Good round-trip deal | $296 or less |
Good one-way deal | $152 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 November 12, 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
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Tue 12/8
6:15 am-1:15 pm
1 stop6h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$103
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Tue 12/8
4:24 pm-1:34 am
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sat 12/5
4:34 pm-1:34 am
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$105
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Thu 12/31
5:30 am-9:00 pm
2 stops14h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Wed 1/6
6:00 am-1:32 pm
1 stop6h 32m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Wed 1/20
6:00 am-2:40 pm
1 stop7h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$117
NorfolkNassau
ORF Norfolk - NAS Nassau Intl
ORFNAS
Norfolk
Sat 1/23
7:17 pm-11:04 am
1 stop15h 47m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
NorfolkNassau
ORF Norfolk - NAS Nassau Intl
ORFNAS
Norfolk
Tue 12/1
5:30 am-1:50 pm
1 stop8h 20m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
NorfolkNassau
ORF Norfolk - NAS Nassau Intl
ORFNAS
Norfolk
Sun 11/29
7:20 pm-9:27 am
1 stop14h 07m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
NorfolkNassau
ORF Norfolk - NAS Nassau Intl
ORFNAS
Norfolk
Tue 12/1
6:00 am-1:22 pm
2 stops7h 22m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
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.
RIC-SJU
ORF-SJU
ORF-NAS
RIC-AUA
RIC-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia to Caribbean
USVA-0CB
RIC-SJU
ORF-SJU
ORF-NAS
RIC-AUA
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 $472). Flying from Virginia to Caribbean in December is currently the most expensive (average of $623). 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.
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 50 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.
Alternative routes
Complete your trip
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Other flight options
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Return Flight Options
Top countries
Top destinations
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 November 12, 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 November 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$300 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$495 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$548 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$203 | Average$541 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$615 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$236 | Average$640 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |