$103+ Cheap flights from Virginia to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from Virginia to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Virginia to Caribbean
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Cheapest flights from Virginia to CaribbeanExplore the most affordable flight options available from Virginia to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
Explore the most affordable flight options available from Virginia to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 2026.
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/158:17 am -
1 stop14h 42m
Wed 11/183:53 pm -
1 stop8h 08m
Deal found 10/30![American Airlines logo]()
$240
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/125:15 pm -
1 stop6h 32m
Deal found 11/1![JetBlue logo]()
$243
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/127:44 pm -
1 stop12h 52m
Sat 12/194:31 pm -
1 stop7h 22m
Deal found 11/1![American Airlines logo]()
$244
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates ” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:59 pm -
1 stop7h 00m
Wed 12/911:40 am -
1 stop6h 28m
Deal found 11/1![JetBlue logo]()
$246
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 stop21h 45m
Sat 11/143:55 am -
1 stop12h 03m
Deal found 11/2![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:53 pm -
1 stop9h 53m
Fri 11/2010:21 pm -
1 stop17h 13m
Deal found 11/2![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/183:55 am -
1 stop12h 03m
Deal found 11/2![Frontier logo]()
$250
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 12/47:40 pm -
1 stop12h 56m
Sat 12/127:00 am -
1 stop17h 01m
Deal found 10/30![American Airlines logo]()
$252
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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
Wed 11/187:00 am -
1 stop8h 43m
Deal found 10/31![JetBlue logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/83:53 pm -
1 stop17h 22m
Sat 11/143:55 am -
1 stop12h 03m
Deal found 10/31![Frontier logo]()
$254
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/151:31 pm -
1 stop10h 28m
Sun 11/153:55 am -
1 stop11h 54m
Deal found 11/1![Frontier logo]()
$254
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/185:45 am -
1 stop11h 20m
Sat 11/217:06 am -
1 stop11h 20m
Deal found 10/31![American Airlines logo]()
$255
Best flights from Virginia to CaribbeanDiscover carefully curated flight deals from Virginia to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Virginia to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/142:20 pm -
1 stop9h 16m
Wed 1/208:05 am -
1 stop6h 40m
Deal found 10/31![United Airlines logo]()
$281
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/67:04 am -
1 stop6h 06m
Tue 2/99:05 am -
Nonstop3h 45m
Deal found 11/3![JetBlue logo]()
$288
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/2712:35 pm -
2 stops11h 00m
Tue 2/27:25 am -
2 stops10h 30m
Deal found 11/3![Southwest logo]()
$297
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 2/17:21 pm -
2 stops18h 58m
Thu 2/45:13 pm -
1 stop6h 56m
Deal found 10/30![American Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/214:59 pm -
1 stop6h 59m
Sun 1/247:17 am -
1 stop9h 59m
Deal found 11/2![Delta logo]()
$317
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/206:30 pm -
1 stop5h 57m
Tue 2/2311:50 am -
Nonstop3h 49m
Deal found 11/3![JetBlue logo]()
$293
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/276:20 am -
1 stop6h 27m
Wed 2/109:25 am -
Nonstop3h 29m
Deal found 11/2![JetBlue logo]()
$301
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Tue 1/196:15 am -
1 stop6h 00m
Tue 1/265:50 pm -
1 stop6h 53m
Deal found 10/30![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/245:40 am -
1 stop7h 05m
Sun 1/317:17 am -
1 stop9h 32m
Deal found 10/30![Delta logo]()
$337
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 am -
1 stop6h 32m
Sat 12/55:50 pm -
1 stop6h 22m
Deal found 11/3![United Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/27:00 am -
1 stop8h 54m
Tue 12/87:00 am -
1 stop10h 10m
Deal found 11/1![Delta logo]()
$361
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/2712:45 pm -
Nonstop3h 25m
Sat 12/53:50 pm -
1 stop6h 09m
Deal found 11/1![JetBlue logo]()
$336
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 3/316:00 am -
2 stops15h 24m
Wed 4/74:55 pm -
1 stop6h 41m
Deal found 11/3![United Airlines logo]()
$344
This Southwest deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/159:55 am -
2 stops9h 55m
Thu 11/196:10 am -
2 stops9h 15m
Deal found 10/31![Southwest logo]()
$418
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:00 am -
1 stop13h 05m
Sun 12/1312:15 pm -
1 stop11h 22m
Deal found 10/31![American Airlines logo]()
$419
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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
Sat 11/142:02 pm -
1 stop9h 09m
Deal found 10/31![JetBlue logo]()
$347
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/133:15 pm -
1 stop7h 20m
Deal found 11/1![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/87:28 am -
1 stop6h 02m
Fri 11/1310:20 am -
2 stops9h 30m
Deal found 10/30![American Airlines logo]()
$437
This Southwest deal was found by Cheapflights users on 10/30. 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.
Thu 1/2812:35 pm -
2 stops11h 00m
Sun 1/317:20 am -
2 stops11h 00m
Deal found 10/30![Southwest logo]()
$437
This JetBlue deal was found by Cheapflights users on 10/30. 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.
Thu 1/2812:40 pm -
Nonstop3h 29m
Sat 2/65:19 pm -
1 stop6h 05m
Deal found 10/30![JetBlue logo]()
$357
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/75:23 am -
1 stop11h 34m
Fri 12/116:12 pm -
1 stop6h 38m
Deal found 11/1![Delta logo]()
$393
This Southwest deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 4/1512:55 pm -
1 stop7h 10m
Sun 4/185:00 am -
1 stop8h 20m
Deal found 11/1![Southwest logo]()
$438
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 -
1 stop7h 48m
Tue 1/262:54 pm -
1 stop19h 16m
Deal found 11/2![United Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/246:00 am -
1 stop10h 20m
Mon 3/15:55 pm -
2 stops16h 51m
Deal found 11/3![American Airlines logo]()
$454
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 11/278:20 pm -
1 stop16h 20m
Fri 12/45:35 pm -
1 stop16h 45m
Deal found 10/30![United Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:00 am -
1 stop4h 53m
Thu 12/2412:27 pm -
2 stops9h 19m
Deal found 10/31![American Airlines logo]()
$456
This JetBlue deal was found by Cheapflights users on 10/30. 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.
Sat 4/241:40 pm -
Nonstop4h 07m
Sat 5/18:50 am -
Nonstop3h 55m
Deal found 10/30![JetBlue logo]()
$379
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 4/226:00 am -
1 stop9h 45m
Thu 4/291:10 pm -
1 stop11h 02m
Deal found 11/1![Delta logo]()
$425
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/236:00 am -
1 stop9h 40m
Wed 1/274:40 pm -
2 stops17h 52m
Deal found 11/2![United Airlines logo]()
$411
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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
Thu 12/103:50 pm -
1 stop6h 09m
Deal found 11/3![JetBlue logo]()
$381
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated November 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/83:53 pm -
1 stop17h 22m
Sat 11/143:55 am -
1 stop12h 03m
Deal found 10/31![Frontier logo]()
$254
This JetBlue deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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
Wed 11/187:00 am -
1 stop8h 43m
Deal found 10/31![JetBlue logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 stop21h 45m
Sat 11/143:55 am -
1 stop12h 03m
Deal found 11/2![Frontier logo]()
$248
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/158:17 am -
1 stop14h 42m
Wed 11/183:53 pm -
1 stop8h 08m
Deal found 10/30![American Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:53 pm -
1 stop9h 53m
Fri 11/2010:21 pm -
1 stop17h 13m
Deal found 11/2![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/183:55 am -
1 stop12h 03m
Deal found 11/2![Frontier logo]()
$250
This Frontier deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/151:31 pm -
1 stop10h 28m
Sun 11/153:55 am -
1 stop11h 54m
Deal found 11/1![Frontier logo]()
$254
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 11/185:45 am -
1 stop11h 20m
Sat 11/217:06 am -
1 stop11h 20m
Deal found 10/31![American Airlines logo]()
$255
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/125:15 pm -
1 stop6h 32m
Deal found 11/1![JetBlue logo]()
$243
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 12/47:40 pm -
1 stop12h 56m
Sat 12/127:00 am -
1 stop17h 01m
Deal found 10/30![American Airlines logo]()
$252
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:59 pm -
1 stop7h 00m
Wed 12/911:40 am -
1 stop6h 28m
Deal found 11/1![JetBlue logo]()
$246
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/127:44 pm -
1 stop12h 52m
Sun 12/207:00 am -
1 stop12h 00m
Deal found 11/1![American Airlines logo]()
$244
One-way flights from Virginia to CaribbeanSearch for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Southwest deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/103:05 pm -
1 stop7h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Southwest logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:09 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/21:59 pm -
1 stop11h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/912:45 pm -
Nonstop3h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$107
This Priceline deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/75:09 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:45 pm -
Nonstop3h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![JetBlue logo]()
$117
This Delta deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 1/195:30 am -
1 stop6h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$118
This JetBlue deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:34 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![JetBlue logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:53 pm -
1 stop9h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$123
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 stop9h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![United Airlines logo]()
$123
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Fri 12/115:09 pm -
1 stop8h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$128
This American Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” 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 1/197:21 pm -
2 stops18h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/31![American Airlines logo]()
$129
Find flight deals from Virginia to Caribbean
Keep the following information in mind while searching for Virginia to Caribbean flight deals. Data was last updated November 4, 2026.
Round-trip from | $240 (American Airlines) |
|---|---|
One-way from | $103 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $385 |
Good round-trip deal | $317 or less |
Good one-way deal | $152 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Virginia to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 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
Sun 12/6
5:55 pm-1:10 am
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$103
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Thu 12/10
3:05 pm-11:25 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$108
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
$118
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Sat 12/5
4:34 pm-1:34 am
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$121
RichmondOranjestad
RIC Richmond Byrd Intl - AUA Oranjestad Reina Beatrix
RICAUA
Richmond Byrd Intl
Tue 1/19
6:15 am-4:25 pm
1 stop9h 10m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$123
RichmondOranjestad
RIC Richmond Byrd Intl - AUA Oranjestad Reina Beatrix
RICAUA
Richmond Byrd Intl
Tue 1/19
7:21 pm-3:19 pm
2 stops18h 58m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
NorfolkNassau
ORF Norfolk - NAS Nassau Intl
ORFNAS
Norfolk
Sat 1/2
8:27 pm-9:22 am
1 stop12h 55m
Nassau Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$132
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
$133
RichmondSan Juan
RIC Richmond Byrd Intl - SJU San Juan Luis Munoz Marin Intl
RICSJU
Richmond Byrd Intl
Tue 11/10
7:00 am-4:56 pm
1 stop8h 56m
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 11/14
3:34 pm-1:13 am
1 stop8h 39m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$151
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
RIC-MBJ
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 $466). Flying from Virginia to Caribbean in December is currently the most expensive (average of $621). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from VA to CB?
Find hourly flight availability from Virginia to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 4, 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 68 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 November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean
Find the right flight back to Virginia after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Virginia to Caribbean flights
Consider these flights traveling from Virginia to Caribbean.
Top 7 airlines flying from Virginia to Caribbean
Discover the top 7 airlines that operate flights from Virginia to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$308 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$493 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$542 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$203 | Average$540 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$612 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$633 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |