$101+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Nov 13 — Nov 201
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 October 14, 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 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 stop17h 22m
Thu 11/199:20 am -
1 stop6h 38m
Deal found 10/13![Frontier logo]()
$238
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Sun 10/256:00 am -
1 stop8h 09m
Tue 10/278:00 am -
1 stop7h 59m
Deal found 10/11![JetBlue logo]()
$239
This JetBlue deal was found by Cheapflights users on 10/10. 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 10/244:51 pm -
1 stop6h 55m
Sat 10/316:00 am -
1 stop6h 05m
Deal found 10/10![JetBlue logo]()
$240
This JetBlue deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/166:00 am -
1 stop8h 33m
Fri 11/205:01 am -
1 stop10h 00m
Deal found 10/13![JetBlue logo]()
$241
This JetBlue deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/13![JetBlue logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Sat 10/241:40 pm -
Nonstop3h 40m
Tue 10/279:00 am -
Nonstop3h 42m
Deal found 10/10![JetBlue logo]()
$243
This JetBlue deal was found by Cheapflights users on 10/10. 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.
Sun 10/256:00 am -
1 stop8h 09m
Thu 10/299:00 am -
1 stop6h 59m
Deal found 10/10![JetBlue logo]()
$244
This JetBlue deal was found by Cheapflights users on 10/12. 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 10/271:40 pm -
Nonstop3h 38m
Sat 10/319:00 am -
Nonstop3h 42m
Deal found 10/12![JetBlue logo]()
$245
This Frontier deal was found by Cheapflights users on 10/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/91:59 pm -
1 stop11h 14m
Sun 12/133:43 am -
1 stop10h 21m
Deal found 10/12![Frontier logo]()
$248
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Thu 10/293:51 pm -
1 stop9h 59m
Sat 10/313:55 am -
1 stop11h 58m
Deal found 10/9![Frontier logo]()
$251
This Delta deal was found by Cheapflights users on 10/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:30 am -
1 stop6h 16m
Fri 12/116:59 pm -
1 stop6h 59m
Deal found 10/10![Delta logo]()
$254
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Mon 11/234:54 pm -
1 stop16h 05m
Wed 12/23:59 pm -
1 stop25h 11m
Deal found 10/9![Frontier logo]()
$256
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 14, 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 14, 2026.
This JetBlue deal was found by Cheapflights users on 10/12. 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 10/271:40 pm -
Nonstop3h 38m
Sat 10/319:00 am -
Nonstop3h 42m
Deal found 10/12![JetBlue logo]()
$245
This United Airlines deal was found by Cheapflights users on 10/9. 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 1/66:00 am -
1 stop9h 40m
Wed 1/135:50 pm -
1 stop16h 42m
Deal found 10/9![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 10/11. 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 1/69:45 am -
1 stop10h 15m
Wed 1/277:30 am -
1 stop8h 48m
Deal found 10/11![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 10/11. 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 10/293:05 pm -
1 stop9h 05m
Mon 11/25:35 am -
1 stop7h 15m
Deal found 10/11![Southwest logo]()
$340
This American Airlines deal was found by Cheapflights users on 10/9. 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 11/307:54 pm -
1 stop15h 27m
Sat 12/54:23 pm -
1 stop7h 31m
Deal found 10/9![American Airlines logo]()
$368
This JetBlue deal was found by Cheapflights users on 10/11. 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 10/293:14 pm -
1 stop8h 59m
Mon 11/26:01 am -
1 stop6h 51m
Deal found 10/11![JetBlue logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Mon 1/115:14 pm -
1 stop22h 26m
Sun 1/176:42 pm -
2 stops41h 52m
Deal found 10/9![Multiple Airlines logo]()
$562
This JetBlue deal was found by Cheapflights users on 10/10. 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.
Tue 11/36:00 am -
1 stop8h 32m
Wed 11/116:25 am -
1 stop8h 58m
Deal found 10/10![JetBlue logo]()
$261
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Mon 1/188:05 am -
1 stop7h 45m
Fri 1/226:00 pm -
2 stops20h 45m
Deal found 10/9![United Airlines logo]()
$310
This JetBlue deal was found by Cheapflights users on 10/9. 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.
Sat 10/174:51 pm -
1 stop6h 55m
Tue 10/206:01 am -
1 stop7h 44m
Deal found 10/9![JetBlue logo]()
$280
This Delta deal was found by Cheapflights users on 10/12. 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.
Tue 11/105:30 am -
1 stop10h 03m
Tue 11/174:58 pm -
1 stop5h 35m
Deal found 10/12![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 10/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/712:15 pm -
2 stops10h 25m
Fri 2/127:25 am -
2 stops9h 05m
Deal found 10/10![Southwest logo]()
$368
This American Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop5h 01m
Fri 11/1311:51 am -
2 stops9h 25m
Deal found 10/9![American Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 1/196:15 am -
1 stop6h 00m
Tue 1/265:50 pm -
1 stop6h 53m
Deal found 10/13![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 10/11. 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 11/85:30 am -
1 stop6h 20m
Fri 11/134:58 pm -
1 stop7h 50m
Deal found 10/11![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:00 pm -
1 stop6h 15m
Tue 10/275:50 am -
1 stop6h 00m
Deal found 10/13![Southwest logo]()
$374
This JetBlue deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:51 pm -
1 stop6h 55m
Sun 11/16:01 am -
1 stop6h 51m
Deal found 10/13![JetBlue logo]()
$316
This American Airlines deal was found by Cheapflights users on 10/9. 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.
Fri 10/301:37 pm -
2 stops6h 32m
Thu 11/56:45 pm -
1 stop5h 19m
Deal found 10/9![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 stop6h 50m
Wed 12/165:01 pm -
1 stop5h 34m
Deal found 10/13![Delta logo]()
$368
This United Airlines deal was found by Cheapflights users on 10/9. 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.
Sun 1/106:00 am -
1 stop9h 40m
Sat 1/165:50 pm -
1 stop16h 42m
Deal found 10/9![United Airlines logo]()
$384
This JetBlue deal was found by Cheapflights users on 10/9. 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 12/45:59 pm -
1 stop7h 00m
Sat 12/128:00 am -
1 stop8h 44m
Deal found 10/9![JetBlue logo]()
$319
This American Airlines deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/13![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/105:40 am -
1 stop6h 25m
Sun 1/177:00 am -
1 stop11h 07m
Deal found 10/9![Delta logo]()
$376
This Southwest deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 10/302:10 pm -
2 stops10h 15m
Mon 11/25:35 am -
2 stops10h 15m
Deal found 10/13![Southwest logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/11. 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 1/186:00 am -
1 stop9h 40m
Sat 1/236:00 pm -
2 stops16h 32m
Deal found 10/11![United Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 10/12. 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.
Sat 12/127:14 pm -
2 stops18h 05m
Wed 12/161:07 pm -
2 stops9h 08m
Deal found 10/12![American Airlines logo]()
$428
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.
Wed 1/2712:50 pm -
2 stops10h 50m
Sun 1/315:35 am -
2 stops11h 35m
Deal found 10/14![Southwest logo]()
$434
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.
Wed 11/46:00 am -
1 stop5h 50m
Tue 11/101:15 pm -
1 stop8h 22m
Deal found 10/14![Delta logo]()
$430
This United Airlines deal was found by Cheapflights users on 10/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:15 am -
3 stops17h 21m
Sat 10/314:50 pm -
1 stop6h 54m
Deal found 10/12![United Airlines logo]()
$434
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Tue 1/196:30 am -
1 stop8h 53m
Fri 1/299:25 am -
Nonstop3h 29m
Deal found 10/11![JetBlue logo]()
$405
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated October 14, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated October 14, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 10/10. 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 10/244:51 pm -
1 stop6h 55m
Sat 10/316:00 am -
1 stop6h 05m
Deal found 10/10![JetBlue logo]()
$240
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Sat 10/241:40 pm -
Nonstop3h 40m
Tue 10/279:00 am -
Nonstop3h 42m
Deal found 10/10![JetBlue logo]()
$243
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Sun 10/256:00 am -
1 stop8h 09m
Tue 10/278:00 am -
1 stop7h 59m
Deal found 10/11![JetBlue logo]()
$239
This JetBlue deal was found by Cheapflights users on 10/10. 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.
Sun 10/256:00 am -
1 stop8h 09m
Thu 10/299:00 am -
1 stop6h 59m
Deal found 10/10![JetBlue logo]()
$244
This Frontier deal was found by Cheapflights users on 10/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/263:48 pm -
1 stop10h 05m
Thu 10/292:55 am -
1 stop11h 54m
Deal found 10/11![Frontier logo]()
$260
This JetBlue deal was found by Cheapflights users on 10/12. 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 10/271:40 pm -
Nonstop3h 38m
Sat 10/319:00 am -
Nonstop3h 42m
Deal found 10/12![JetBlue logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Thu 10/293:51 pm -
1 stop9h 59m
Sat 10/313:55 am -
1 stop11h 58m
Deal found 10/9![Frontier logo]()
$251
This JetBlue deal was found by Cheapflights users on 10/11. 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.
Fri 10/3012:55 pm -
1 stop7h 45m
Mon 11/28:00 am -
1 stop9h 05m
Deal found 10/11![JetBlue logo]()
$248
This United Airlines deal was found by Cheapflights users on 10/11. 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.
Tue 11/106:00 am -
2 stops14h 00m
Thu 11/125:50 pm -
1 stop6h 54m
Deal found 10/11![United Airlines logo]()
$254
This Cheapflightsfares deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 stop17h 22m
Thu 11/199:20 am -
1 stop6h 38m
Deal found 10/13![Frontier logo]()
$238
This JetBlue deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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 11/166:00 am -
1 stop8h 33m
Fri 11/205:01 am -
1 stop10h 00m
Deal found 10/13![JetBlue logo]()
$241
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Mon 11/234:54 pm -
1 stop16h 05m
Wed 12/23:59 pm -
1 stop25h 11m
Deal found 10/9![Frontier logo]()
$256
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 14, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Tue 11/101:44 pm -
1 stop10h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 10/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:31 pm -
1 stop10h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$103
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 11/1712:44 pm -
2 stops25h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![Multiple Airlines logo]()
$107
This JetBlue deal was found by Cheapflights users on 10/9. 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.
Tue 11/106:00 am -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![JetBlue logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 10/10. 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.
Mon 11/93:44 pm -
1 stop10h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 10/10. 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.
Wed 11/117:41 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$117
This Mytrip deal was found by Cheapflights users on 10/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:41 pm -
1 stop6h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Frontier logo]()
$120
This Cheapflightsfares deal was found by Cheapflights users on 10/9. 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.
Thu 10/291:31 pm -
1 stop11h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$121
This JetBlue deal was found by Cheapflights users on 10/12. 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 11/146:00 am -
1 stop7h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![JetBlue logo]()
$122
This Jetabroad deal was found by Cheapflights users on 10/10. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am -
1 stop8h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![JetBlue logo]()
$125
This American Airlines deal was found by Cheapflights users on 10/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:29 pm -
2 stops20h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![American Airlines logo]()
$126
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 14, 2026.
Round-trip from | $238 (Cheapflightsfares) |
|---|---|
One-way from | $101 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $352 |
Good round-trip deal | $325 or less |
Good one-way deal | $200 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 14, 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 11/7
6:00 am-2:33 pm
1 stop7h 33m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Thu 11/12
5:02 pm-12:11 am
1 stop6h 09m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Fri 11/13
5:02 pm-11:57 pm
1 stop5h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$113
RichmondOranjestad
RIC Richmond Byrd Intl - AUA Oranjestad Reina Beatrix
RICAUA
Richmond Byrd Intl
Tue 11/10
5:29 pm-3:10 pm
2 stops20h 41m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$126
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Tue 11/10
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
$127
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Mon 1/11
4:15 pm-11:05 pm
1 stop5h 50m
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
Wed 11/11
12:15 pm-11:54 pm
1 stop10h 39m
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 11/9
12:45 pm-11:15 pm
1 stop9h 30m
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
Tue 11/10
6:00 am-9:00 pm
2 stops14h 00m
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 1/10
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
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-AUA
ORF-NAS
ORF-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
RIC-AUA
ORF-NAS
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 $455). Flying from Virginia to Caribbean in December is currently the most expensive (average of $612). 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 14, 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
Flights by cabin class
Other flight options
Popular flights
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 October 14, 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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$345 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$171 | Average$525 | 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% |