$114+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Nov 18 — Nov 251
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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from 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 October 19, 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 October 19, 2026.
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/135:02 pm -
1 stop5h 55m
Tue 11/177:55 am -
1 stop9h 05m
Deal found 10/14![JetBlue logo]()
$241
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/15:59 pm -
1 stop7h 00m
Tue 12/88:00 am -
1 stop8h 44m
Deal found 10/14![JetBlue logo]()
$242
This JetBlue deal was found by Cheapflights users on 10/15. 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 11/1712:42 pm -
1 stop7h 39m
Wed 11/187:00 am -
1 stop8h 43m
Deal found 10/15![JetBlue logo]()
$245
This JetBlue deal was found by Cheapflights users on 10/15. 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 11/106:00 am -
1 stop7h 33m
Wed 11/187:00 am -
1 stop8h 43m
Deal found 10/15![JetBlue logo]()
$249
This Southwest deal was found by Cheapflights users on 10/15. 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 10/293:05 pm -
1 stop9h 05m
Sat 10/315:45 am -
1 stop6h 00m
Deal found 10/15![Southwest logo]()
$254
This Frontier deal was found by Cheapflights users on 10/18. 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.
Tue 11/107:41 pm -
1 stop6h 05m
Wed 11/113:55 am -
1 stop7h 20m
Deal found 10/18![Frontier logo]()
$254
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/233:29 pm -
1 stop17h 30m
Thu 11/2610:21 pm -
1 stop17h 08m
Deal found 10/14![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 10/277:41 pm -
1 stop13h 34m
Mon 11/27:00 am -
2 stops30h 04m
Deal found 10/17![Multiple Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/93:34 pm -
1 stop8h 47m
Fri 11/137:00 am -
1 stop8h 43m
Deal found 10/14![JetBlue logo]()
$256
This CheapOair deal was found by Cheapflights users on 10/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:44 pm -
1 stop10h 02m
Fri 11/209:30 am -
Nonstop3h 25m
Deal found 10/19![Multiple Airlines logo]()
$256
This JetBlue deal was found by Cheapflights users on 10/16. 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.
Mon 11/165:02 pm -
1 stop6h 09m
Mon 11/235:01 am -
1 stop10h 00m
Deal found 10/16![JetBlue logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Fri 12/45:30 pm -
1 stop7h 41m
Mon 12/711:00 am -
1 stop22h 53m
Deal found 10/18![Multiple Airlines logo]()
$258
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 October 19, 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 October 19, 2026.
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/74:58 pm -
1 stop6h 54m
Thu 11/127:00 am -
1 stop10h 09m
Deal found 10/14![Delta logo]()
$272
This United Airlines deal was found by Cheapflights users on 10/16. 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 12/96:00 am -
1 stop6h 32m
Fri 12/112:05 am -
2 stops13h 19m
Deal found 10/16![United Airlines logo]()
$274
This JetBlue deal was found by Cheapflights users on 10/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:59 pm -
1 stop7h 00m
Sat 12/128:50 am -
Nonstop3h 42m
Deal found 10/18![JetBlue logo]()
$305
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 2/49:55 am -
2 stops10h 20m
Tue 2/99:05 am -
2 stops11h 25m
Deal found 10/14![Southwest logo]()
$386
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Mon 2/158:20 pm -
2 stops16h 11m
Thu 2/187:00 am -
2 stops16h 33m
Deal found 10/15![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 10/18. 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 11/105:40 am -
1 stop7h 29m
Wed 11/113:20 pm -
1 stop9h 24m
Deal found 10/18![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 10/17. 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.
Wed 1/207:00 am -
1 stop8h 50m
Wed 1/276:30 pm -
1 stop6h 44m
Deal found 10/17![Delta logo]()
$297
This JetBlue deal was found by Cheapflights users on 10/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:45 pm -
Nonstop3h 27m
Sun 12/69:25 am -
Nonstop3h 26m
Deal found 10/18![JetBlue logo]()
$347
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/146:10 am -
2 stops15h 12m
Tue 11/172:05 am -
2 stops16h 02m
Deal found 10/14![United Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 2/49:55 am -
2 stops10h 20m
Mon 2/85:35 am -
1 stop6h 30m
Deal found 10/14![Southwest logo]()
$386
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/33:34 pm -
1 stop8h 39m
Tue 11/107:00 am -
1 stop8h 43m
Deal found 10/14![JetBlue logo]()
$352
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/233:25 pm -
2 stops8h 35m
Thu 12/36:10 am -
2 stops9h 15m
Deal found 10/14![Southwest logo]()
$388
This Delta deal was found by Cheapflights users on 10/15. 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.
Sat 1/3012:30 pm -
1 stop10h 20m
Tue 2/97:00 am -
1 stop10h 46m
Deal found 10/15![Delta logo]()
$353
This JetBlue deal was found by Cheapflights users on 10/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:40 pm -
Nonstop3h 38m
Mon 11/26:01 am -
1 stop6h 51m
Deal found 10/17![JetBlue logo]()
$357
This United Airlines deal was found by Cheapflights users on 10/17. 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.
Wed 12/26:00 am -
1 stop9h 25m
Wed 12/95:35 pm -
1 stop16h 45m
Deal found 10/17![United Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 10/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/155:45 am -
1 stop6h 41m
Thu 11/195:08 pm -
2 stops20h 04m
Deal found 10/16![American Airlines logo]()
$471
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 2/259:50 am -
2 stops9h 05m
Tue 3/26:15 am -
1 stop11h 30m
Deal found 10/14![Southwest logo]()
$394
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sun 1/106:00 am -
1 stop9h 40m
Sat 1/165:50 pm -
1 stop16h 42m
Deal found 10/16![United Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 10/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:06 am -
1 stop7h 04m
Sat 1/305:04 pm -
2 stops18h 12m
Deal found 10/19![American Airlines logo]()
$478
This JetBlue deal was found by Cheapflights users on 10/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop9h 09m
Fri 11/279:30 am -
Nonstop3h 25m
Deal found 10/18![JetBlue logo]()
$406
This United Airlines deal was found by Cheapflights users on 10/15. 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 11/36:10 am -
2 stops14h 14m
Tue 11/102:05 am -
2 stops16h 02m
Deal found 10/15![United Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 10/17. 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.
Thu 12/176:03 am -
1 stop9h 42m
Wed 12/234:35 pm -
1 stop6h 54m
Deal found 10/17![Delta logo]()
$419
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/229:55 am -
2 stops10h 20m
Wed 1/279:05 am -
2 stops11h 25m
Deal found 10/14![Southwest logo]()
$454
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sun 1/176:00 pm -
1 stop17h 40m
Fri 1/221:50 pm -
1 stop9h 25m
Deal found 10/16![United Airlines logo]()
$415
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/57:30 pm -
1 stop17h 16m
Tue 11/105:33 pm -
2 stops18h 08m
Deal found 10/14![American Airlines logo]()
$509
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/96:00 am -
1 stop8h 57m
Fri 11/131:07 pm -
1 stop10h 12m
Deal found 10/14![JetBlue logo]()
$429
This Delta deal was found by Cheapflights users on 10/17. 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.
Mon 11/238:30 am -
1 stop7h 26m
Thu 11/268:00 am -
1 stop9h 29m
Deal found 10/17![Delta logo]()
$452
This American Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 pm -
1 stop15h 28m
Tue 11/105:33 pm -
1 stop17h 54m
Deal found 10/14![American Airlines logo]()
$511
This Southwest deal was found by Cheapflights users on 10/16. 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.
Thu 1/286:05 am -
1 stop6h 15m
Tue 2/23:45 pm -
1 stop6h 40m
Deal found 10/16![Southwest logo]()
$468
This JetBlue deal was found by Cheapflights users on 10/16. 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.
Sun 11/156:00 am -
1 stop8h 23m
Thu 11/196:35 am -
1 stop8h 26m
Deal found 10/16![JetBlue logo]()
$435
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated October 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 10/277:41 pm -
1 stop13h 34m
Mon 11/27:00 am -
2 stops30h 04m
Deal found 10/17![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 10/277:41 pm -
1 stop13h 34m
Tue 11/37:23 am -
1 stop12h 21m
Deal found 10/17![Frontier logo]()
$261
This Southwest deal was found by Cheapflights users on 10/15. 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 10/293:05 pm -
1 stop9h 05m
Sat 10/315:45 am -
1 stop6h 00m
Deal found 10/15![Southwest logo]()
$254
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/76:00 am -
1 stop7h 33m
Wed 11/118:58 am -
1 stop6h 25m
Deal found 10/14![JetBlue logo]()
$259
This Expedia deal was found by Cheapflights users on 10/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/83:53 pm -
1 stop21h 45m
Wed 11/113:55 am -
1 stop12h 03m
Deal found 10/18![Frontier logo]()
$260
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/93:34 pm -
1 stop8h 47m
Fri 11/137:00 am -
1 stop8h 43m
Deal found 10/14![JetBlue logo]()
$256
This JetBlue deal was found by Cheapflights users on 10/15. 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 11/106:00 am -
1 stop7h 33m
Wed 11/187:00 am -
1 stop8h 43m
Deal found 10/15![JetBlue logo]()
$249
This Frontier deal was found by Cheapflights users on 10/18. 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.
Tue 11/107:41 pm -
1 stop6h 05m
Wed 11/113:55 am -
1 stop7h 20m
Deal found 10/18![Frontier logo]()
$254
This JetBlue deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/135:02 pm -
1 stop5h 55m
Tue 11/177:55 am -
1 stop9h 05m
Deal found 10/14![JetBlue logo]()
$241
This CheapOair deal was found by Cheapflights users on 10/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:44 pm -
1 stop10h 02m
Fri 11/209:30 am -
Nonstop3h 25m
Deal found 10/18![Multiple Airlines logo]()
$256
This JetBlue deal was found by Cheapflights users on 10/16. 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.
Mon 11/165:02 pm -
1 stop6h 09m
Mon 11/235:01 am -
1 stop10h 00m
Deal found 10/16![JetBlue logo]()
$258
This JetBlue deal was found by Cheapflights users on 10/15. 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 11/1712:42 pm -
1 stop7h 39m
Wed 11/187:00 am -
1 stop8h 43m
Deal found 10/15![JetBlue logo]()
$245
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 October 19, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:56 pm -
1 stop8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/234:54 pm -
1 stop16h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$115
This Priceline deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/117:41 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$117
This JetBlue deal was found by Cheapflights users on 10/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:00 am -
1 stop8h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![JetBlue logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 12/119:22 pm -
1 stop27h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 10/277:41 pm -
1 stop13h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$124
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:44 pm -
1 stop10h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Frontier logo]()
$125
This Jetabroad deal was found by Cheapflights users on 10/16. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:02 pm -
1 stop5h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![JetBlue logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 11/23:44 pm -
1 stop17h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Frontier logo]()
$127
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” 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 1/114:25 pm -
1 stop6h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Delta logo]()
$128
This Priceline deal was found by Cheapflights users on 10/17. 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 Priceline 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 10/17![Frontier logo]()
$130
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Mon 11/168:20 pm -
2 stops17h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$130
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 October 19, 2026.
Round-trip from | $242 (JetBlue) |
|---|---|
One-way from | $114 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $344 |
Good round-trip deal | $316 or less |
Good one-way deal | $174 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 October 19, 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
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sat 11/14
6:00 am-3:33 pm
1 stop8h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Tue 1/12
5:40 am-1:05 pm
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Mon 1/11
4:25 pm-11:50 pm
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sun 1/17
1:00 pm-11:50 pm
1 stop9h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
RichmondOranjestad
RIC Richmond Byrd Intl - AUA Oranjestad Reina Beatrix
RICAUA
Richmond Byrd Intl
Mon 11/16
8:20 pm-3:00 pm
2 stops17h 40m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
RichmondOranjestad
RIC Richmond Byrd Intl - AUA Oranjestad Reina Beatrix
RICAUA
Richmond Byrd Intl
Mon 12/28
7:57 pm-12:30 pm
1 stop15h 33m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$133
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sat 10/31
3:34 pm-12:13 am
1 stop8h 39m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Wed 12/9
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
$137
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Sat 11/14
6:10 am-10:22 pm
2 stops15h 12m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Wed 12/9
12:45 pm-5:12 pm
Nonstop3h 27m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
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
RIC-STI
RIC-AUA
ORF-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
RIC-SJU
ORF-SJU
RIC-STI
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 $460). Flying from Virginia to Caribbean in December is currently the most expensive (average of $614). 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 October 19, 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.
Alternative routes
Complete your trip
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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 October 19, 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 October 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$332 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$489 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$534 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$605 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$631 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |