$108+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 30 — Nov 61
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 September 30, 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 September 30, 2026.
This JetBlue deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/246:00 am -
1 stop7h 27m
Fri 10/302:50 pm -
1 stop6h 09m
Deal found 9/28![JetBlue logo]()
$218
This Frontier deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/207:41 pm -
1 stop6h 12m
Wed 10/217:20 am -
1 stop11h 26m
Deal found 9/28![Frontier logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/217:41 pm -
1 stop21h 56m
Mon 10/267:44 pm -
1 stop23h 00m
Deal found 9/29![Frontier logo]()
$234
This Frontier deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 12/141:59 pm -
1 stop11h 14m
Tue 12/153:43 am -
1 stop10h 21m
Deal found 9/27![Frontier logo]()
$237
This Frontier deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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.
Fri 12/41:59 pm -
1 stop11h 12m
Fri 12/117:17 am -
1 stop6h 47m
Deal found 9/29![Frontier logo]()
$238
This JetBlue deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:25 pm -
1 stop6h 44m
Sat 10/312:50 pm -
1 stop8h 29m
Deal found 9/30![JetBlue logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 12/45:09 pm -
1 stop8h 02m
Mon 12/75:01 am -
1 stop14h 35m
Deal found 9/28![Frontier logo]()
$241
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/207:22 pm -
1 stop16h 09m
Tue 10/2710:36 am -
2 stops10h 51m
Deal found 9/28![American Airlines logo]()
$242
This Priceline deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/293:51 pm -
1 stop9h 59m
Sat 10/319:00 am -
Nonstop3h 42m
Deal found 9/29![Multiple Airlines logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/211:20 pm -
Nonstop3h 32m
Mon 10/269:00 am -
Nonstop3h 26m
Deal found 9/29![JetBlue logo]()
$243
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/187:41 pm -
1 stop13h 37m
Sat 10/2410:39 am -
1 stop8h 07m
Deal found 9/29![Frontier logo]()
$244
This JetBlue deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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
Tue 11/35:30 pm -
1 stop6h 49m
Deal found 9/29![JetBlue logo]()
$245
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 September 30, 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 September 30, 2026.
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:05 pm -
1 stop7h 10m
Tue 10/206:10 am -
1 stop8h 00m
Deal found 9/26![JetBlue logo]()
$249
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/136:15 am -
1 stop6h 19m
Fri 10/161:25 pm -
2 stops10h 19m
Deal found 9/29![United Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/206:06 am -
1 stop11h 19m
Wed 1/2710:32 am -
1 stop14h 25m
Deal found 9/29![American Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/195:50 am -
1 stop7h 15m
Sat 1/237:00 am -
1 stop10h 46m
Deal found 9/27![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/74:40 pm -
1 stop5h 40m
Fri 12/1111:20 am -
2 stops10h 35m
Deal found 9/25![Southwest logo]()
$399
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:45 pm -
Nonstop3h 27m
Wed 12/163:30 pm -
1 stop6h 29m
Deal found 9/25![JetBlue logo]()
$253
This JetBlue deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/234:37 pm -
1 stop7h 12m
Fri 10/302:50 pm -
1 stop8h 29m
Deal found 9/29![JetBlue logo]()
$257
This United deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
2 stops28h 14m
Mon 10/262:00 pm -
2 stops9h 44m
Deal found 9/30![Multiple Airlines logo]()
$616
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 1/117:30 am -
1 stop8h 20m
Fri 1/155:50 pm -
1 stop16h 15m
Deal found 9/30![United Airlines logo]()
$329
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/23:34 pm -
1 stop8h 39m
Thu 11/127:00 am -
1 stop8h 43m
Deal found 9/26![JetBlue logo]()
$272
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:17 pm -
2 stops20h 30m
Thu 11/195:59 pm -
2 stops19h 03m
Deal found 9/25![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/118:17 am -
1 stop7h 16m
Wed 11/184:58 pm -
1 stop5h 35m
Deal found 9/27![Delta logo]()
$368
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:20 am -
1 stop6h 29m
Wed 12/93:30 pm -
1 stop6h 29m
Deal found 9/25![JetBlue logo]()
$280
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/196:00 am -
2 stops14h 00m
Mon 1/252:05 am -
1 stop9h 05m
Deal found 9/29![United Airlines logo]()
$342
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/128:17 am -
1 stop5h 13m
Thu 11/196:45 pm -
1 stop5h 32m
Deal found 9/28![American Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/116:15 am -
2 stops14h 09m
Mon 11/162:05 am -
2 stops13h 17m
Deal found 9/29![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/303:05 pm -
2 stops9h 20m
Mon 11/211:20 am -
2 stops10h 35m
Deal found 9/29![Southwest logo]()
$414
This JetBlue deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:40 pm -
Nonstop3h 40m
Thu 10/152:37 pm -
1 stop8h 42m
Deal found 9/26![JetBlue logo]()
$301
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
1 stop5h 20m
Tue 11/312:08 pm -
2 stops10h 53m
Deal found 9/25![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/57:39 pm -
1 stop15h 51m
Wed 2/104:35 pm -
1 stop8h 37m
Deal found 9/28![Delta logo]()
$421
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/296:00 am -
1 stop7h 11m
Mon 11/21:00 pm -
1 stop9h 59m
Deal found 9/29![United Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/88:06 pm -
1 stop14h 38m
Fri 11/132:44 pm -
1 stop9h 20m
Deal found 9/30![American Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 12/1111:30 am -
2 stops10h 25m
Thu 12/1712:40 pm -
2 stops10h 15m
Deal found 9/30![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 1/248:00 pm -
2 stops15h 49m
Wed 2/1012:55 pm -
1 stop9h 48m
Deal found 9/29![United Airlines logo]()
$368
This Southwest deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 11/96:15 am -
1 stop6h 35m
Thu 11/122:40 pm -
1 stop8h 20m
Deal found 9/27![Southwest logo]()
$468
This American Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 11/197:29 pm -
1 stop13h 58m
Tue 11/242:26 pm -
1 stop7h 15m
Deal found 9/29![American Airlines logo]()
$388
This JetBlue deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/306:00 am -
1 stop7h 51m
Tue 11/312:21 pm -
1 stop10h 58m
Deal found 9/25![JetBlue logo]()
$358
This United Airlines deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/206:00 am -
1 stop9h 42m
Tue 10/201:00 am -
2 stops8h 42m
Deal found 9/27![United Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 9/28![American Airlines logo]()
$392
This JetBlue deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/26:25 am -
1 stop8h 58m
Deal found 9/28![JetBlue logo]()
$369
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated September 30, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated September 30, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/171:40 pm -
Nonstop3h 40m
Tue 10/209:00 am -
Nonstop3h 39m
Deal found 9/28![JetBlue logo]()
$246
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/187:41 pm -
1 stop13h 37m
Sat 10/2410:39 am -
1 stop8h 07m
Deal found 9/29![Frontier logo]()
$244
This Frontier deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/207:41 pm -
1 stop6h 12m
Wed 10/217:20 am -
1 stop11h 26m
Deal found 9/28![Frontier logo]()
$231
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates ” 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 10/206:00 am -
2 stops9h 38m
Tue 10/2710:36 am -
2 stops10h 51m
Deal found 9/28![American Airlines logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/217:41 pm -
1 stop21h 56m
Mon 10/267:44 pm -
1 stop23h 00m
Deal found 9/29![Frontier logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/211:20 pm -
Nonstop3h 32m
Mon 10/269:00 am -
Nonstop3h 26m
Deal found 9/29![JetBlue logo]()
$243
This CheapOair deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/231:28 pm -
Nonstop3h 32m
Mon 10/269:00 am -
Nonstop3h 26m
Deal found 9/28![JetBlue logo]()
$245
This JetBlue deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/246:00 am -
1 stop7h 27m
Fri 10/302:50 pm -
1 stop6h 09m
Deal found 9/28![JetBlue logo]()
$218
This JetBlue deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:25 pm -
1 stop6h 44m
Sat 10/312:50 pm -
1 stop8h 29m
Deal found 9/30![JetBlue logo]()
$241
This Cheapflightsfares deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:51 pm -
1 stop17h 24m
Sat 10/313:55 am -
1 stop11h 58m
Deal found 9/25![Frontier logo]()
$238
This Priceline deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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 10/293:51 pm -
1 stop9h 59m
Sat 10/319:00 am -
Nonstop3h 42m
Deal found 9/29![Multiple Airlines logo]()
$243
This JetBlue deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” 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
Tue 11/35:30 pm -
1 stop6h 49m
Deal found 9/29![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 September 30, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/271:44 pm -
2 stops26h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$117
This American Airlines deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 10/267:59 pm -
1 stop16h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:14 pm -
1 stop15h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![American Airlines logo]()
$122
This Frontier deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:41 pm -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$122
This Cheapflightsfares deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/83:51 pm -
1 stop9h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:41 pm -
1 stop6h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/25![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” 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 11/13:51 pm -
1 stop9h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Frontier logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 9/27. Clicking the “Pick Dates” 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 10/223:50 pm -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Frontier logo]()
$128
This Priceline deal was found by Cheapflights users on 9/28. Clicking the “Pick Dates” 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 11/191:31 pm -
1 stop10h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/28![Frontier logo]()
$128
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 September 30, 2026.
Round-trip from | $218 (JetBlue) |
|---|---|
One-way from | $108 (Cheapflightsfares) |
Popular in | December |
Cheapest in | September |
Average price | $308 |
Good round-trip deal | $296 or less |
Good one-way deal | $182 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 September 30, 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
Wed 10/28
6:15 am-8:00 pm
2 stops13h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
RichmondNassau
RIC Richmond Byrd Intl - NAS Nassau Intl
RICNAS
Richmond Byrd Intl
Mon 11/2
7:14 pm-10:44 am
1 stop15h 30m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$122
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Tue 10/27
1:40 pm-5:18 pm
Nonstop3h 38m
San Juan Luis Munoz Marin Intl
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
4:58 pm-11:44 pm
1 stop6h 46m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Tue 10/27
4:58 pm-11:44 pm
1 stop6h 46m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sat 10/24
7:25 am-1:45 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$137
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sun 10/25
6:00 am-1:11 pm
1 stop7h 11m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Mon 10/26
6:00 am-1:11 pm
1 stop7h 11m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Wed 10/21
6:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sat 10/24
6:15 am-1:27 pm
1 stop7h 12m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
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.
ORF-SJU
RIC-SJU
RIC-NAS
RIC-PUJ
RIC-AUA
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
ORF-SJU
RIC-SJU
RIC-NAS
RIC-PUJ
What is the cheapest month to book a flight from Virginia to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $453). Flying from Virginia to Caribbean in December is currently the most expensive (average of $627). 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 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 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 September 30, 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 September 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$352 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$510 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$526 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$528 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$596 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$625 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |