$110+ Cheap flights from Virginia to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 2 — Oct 91
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 2, 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 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:30 pm -
1 stop11h 45m
Thu 11/127:00 am -
1 stop7h 58m
Deal found 8/29![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Tue 10/135:26 pm -
1 stop15h 52m
Mon 10/197:00 am -
1 stop6h 59m
Deal found 8/28![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:35 am -
1 stop9h 31m
Sat 10/35:11 pm -
1 stop7h 18m
Deal found 9/1![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:35 am -
1 stop26h 59m
Tue 9/292:57 am -
1 stop12h 04m
Deal found 8/30![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 10/19:35 pm -
1 stop16h 43m
Mon 10/56:42 pm -
1 stop14h 27m
Deal found 8/31![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Wed 10/149:30 pm -
1 stop11h 48m
Wed 10/218:45 am -
1 stop29h 14m
Deal found 8/28![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Wed 9/2310:07 am -
1 stop15h 45m
Mon 9/286:42 pm -
1 stop14h 27m
Deal found 8/28![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 9/2410:35 am -
1 stop26h 59m
Tue 9/292:57 am -
1 stop12h 04m
Deal found 8/31![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Thu 9/241:56 pm -
1 stop25h 26m
Mon 9/286:33 am -
1 stop17h 56m
Deal found 9/2![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Mon 9/219:46 pm -
1 stop11h 49m
Mon 9/282:57 am -
1 stop7h 03m
Deal found 8/31![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:36 pm -
2 stops14h 42m
Mon 11/23:59 pm -
1 stop8h 44m
Deal found 9/1![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:13 pm -
1 stop19h 21m
Sat 9/2610:30 am -
1 stop9h 39m
Deal found 8/30![Frontier logo]()
$294
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 2, 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 2, 2026.
This Southwest deal was found by Cheapflights users on 8/29. 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.
Tue 11/1011:40 am -
1 stop12h 05m
Tue 11/175:50 pm -
1 stop6h 05m
Deal found 8/29![Southwest logo]()
$295
This JetBlue deal was found by Cheapflights users on 9/1. 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.
Sat 10/178:00 am -
Nonstop3h 51m
Tue 10/205:50 pm -
Nonstop3h 51m
Deal found 9/1![JetBlue logo]()
$297
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Mon 9/146:30 am -
1 stop9h 12m
Wed 9/161:00 am -
1 stop7h 57m
Deal found 8/31![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:05 am -
1 stop9h 51m
Tue 11/177:00 am -
1 stop10h 37m
Deal found 8/29![Delta logo]()
$346
This Copa Airlines deal was found by Cheapflights users on 8/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/141:19 am -
1 stop15h 12m
Sun 2/212:47 pm -
1 stop13h 29m
Deal found 8/29![Copa Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 9/1. 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 10/293:25 pm -
2 stops10h 00m
Sun 11/16:05 am -
1 stop13h 10m
Deal found 9/1![Southwest logo]()
$295
This Southwest deal was found by Cheapflights users on 8/29. 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.
Mon 10/265:05 pm -
2 stops8h 20m
Fri 10/306:00 am -
1 stop12h 15m
Deal found 8/29![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
1 stop6h 45m
Wed 9/161:25 pm -
1 stop7h 35m
Deal found 9/1![United Airlines logo]()
$331
This JetBlue deal was found by Cheapflights users on 8/28. 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.
Fri 11/138:00 am -
Nonstop3h 51m
Wed 11/257:00 pm -
Nonstop3h 58m
Deal found 8/28![JetBlue logo]()
$362
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:00 am -
1 stop10h 49m
Sat 9/197:30 am -
1 stop10h 16m
Deal found 8/29![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sat 10/2410:58 am -
1 stop9h 40m
Sat 10/241:05 am -
1 stop9h 19m
Deal found 8/31![United Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 9/511:45 am -
1 stop6h 35m
Fri 9/115:45 pm -
1 stop6h 10m
Deal found 8/31![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sat 11/75:29 pm -
Nonstop3h 53m
Wed 11/118:25 am -
1 stop9h 59m
Deal found 8/31![United Airlines logo]()
$342
This JetBlue deal was found by Cheapflights users on 8/28. 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.
Wed 1/2711:38 am -
Nonstop3h 27m
Mon 2/18:20 am -
Nonstop3h 44m
Deal found 8/28![JetBlue logo]()
$383
This Southwest deal was found by Cheapflights users on 8/31. 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.
Sat 9/198:15 am -
2 stops11h 10m
Sat 9/266:25 am -
1 stop9h 30m
Deal found 8/31![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 8/30. 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 11/310:15 am -
1 stop9h 45m
Tue 11/108:05 am -
Nonstop4h 04m
Deal found 8/30![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 8/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/31:00 pm -
2 stops10h 45m
Tue 11/105:40 am -
2 stops10h 15m
Deal found 8/28![Southwest logo]()
$326
This JetBlue deal was found by Cheapflights users on 8/28. 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 10/105:30 pm -
Nonstop3h 32m
Tue 10/136:10 am -
1 stop7h 01m
Deal found 8/28![JetBlue logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:15 am -
1 stop7h 30m
Sat 9/194:55 pm -
Nonstop3h 52m
Deal found 8/28![United Airlines logo]()
$342
This Copa Airlines deal was found by Cheapflights users on 9/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/31:19 am -
1 stop12h 20m
Mon 2/157:10 am -
1 stop21h 06m
Deal found 9/1![Copa Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 8/30. 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.
Fri 1/297:00 am -
1 stop8h 45m
Sat 2/64:35 pm -
1 stop7h 43m
Deal found 8/30![Delta logo]()
$493
This United Airlines deal was found by Cheapflights users on 9/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:40 am -
Nonstop3h 54m
Sun 10/41:00 am -
1 stop6h 19m
Deal found 9/1![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 8/30. 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 10/24:35 pm -
2 stops8h 45m
Tue 10/66:35 am -
2 stops10h 25m
Deal found 8/30![Southwest logo]()
$343
This Copa Airlines deal was found by Cheapflights users on 8/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/203:36 pm -
1 stop19h 39m
Sat 2/272:28 pm -
1 stop12h 48m
Deal found 8/30![Copa Airlines logo]()
$549
This United Airlines deal was found by Cheapflights users on 8/29. 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.
Mon 10/266:10 am -
1 stop6h 05m
Fri 10/304:50 pm -
Nonstop4h 06m
Deal found 8/29![United Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 8/31. 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.
Fri 9/252:40 pm -
2 stops9h 15m
Wed 9/305:15 am -
2 stops9h 40m
Deal found 8/31![Southwest logo]()
$343
This JetBlue deal was found by Cheapflights users on 9/1. 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 11/67:00 am -
1 stop6h 06m
Thu 11/1912:45 pm -
1 stop10h 43m
Deal found 9/1![JetBlue logo]()
$458
This Delta deal was found by Cheapflights users on 8/28. 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.
Wed 12/306:00 am -
1 stop8h 30m
Thu 1/74:20 pm -
1 stop19h 17m
Deal found 8/28![Delta logo]()
$532
This JetBlue deal was found by Cheapflights users on 8/29. 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.
Wed 10/146:00 am -
1 stop9h 05m
Wed 10/2112:03 pm -
1 stop8h 04m
Deal found 8/29![JetBlue logo]()
$458
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:30 am -
2 stops12h 08m
Sat 10/171:00 am -
1 stop6h 49m
Deal found 8/28![United Airlines logo]()
$346
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated September 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Mon 9/219:46 pm -
1 stop11h 49m
Mon 9/282:57 am -
1 stop7h 03m
Deal found 8/31![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Wed 9/2310:07 am -
1 stop15h 45m
Mon 9/286:42 pm -
1 stop14h 27m
Deal found 8/28![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:13 pm -
1 stop19h 21m
Sat 9/2610:30 am -
1 stop9h 39m
Deal found 8/30![Frontier logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 9/2410:35 am -
1 stop26h 59m
Tue 9/292:57 am -
1 stop12h 04m
Deal found 8/31![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/2. 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.
Thu 9/241:56 pm -
1 stop25h 26m
Mon 9/286:33 am -
1 stop17h 56m
Deal found 9/2![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2610:35 am -
1 stop26h 59m
Tue 9/292:57 am -
1 stop12h 04m
Deal found 8/30![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:35 am -
1 stop9h 31m
Sat 10/35:11 pm -
1 stop7h 18m
Deal found 9/1![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 10/19:35 pm -
1 stop16h 43m
Mon 10/56:42 pm -
1 stop14h 27m
Deal found 8/31![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Tue 10/135:26 pm -
1 stop15h 52m
Mon 10/197:00 am -
1 stop6h 59m
Deal found 8/28![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Tue 10/135:26 pm -
1 stop8h 27m
Mon 10/197:00 am -
2 stops29h 47m
Deal found 8/28![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Wed 10/149:30 pm -
1 stop11h 48m
Wed 10/218:45 am -
1 stop29h 14m
Deal found 8/28![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:36 pm -
2 stops14h 42m
Mon 11/23:59 pm -
1 stop8h 44m
Deal found 9/1![Multiple Airlines logo]()
$293
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 2, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Wed 10/2810:07 am -
1 stop15h 43m
Deal found 8/31![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 8/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/192:49 pm -
1 stop11h 03m
Deal found 8/29![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 8/29. 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.
Thu 11/269:45 am -
Nonstop3h 29m
Deal found 8/29![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Thu 10/297:08 pm -
1 stop17h 27m
Deal found 8/31![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/221:16 pm -
1 stop26h 50m
Deal found 9/1![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Mon 9/289:35 pm -
1 stop12h 00m
Deal found 8/28![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 8/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2910:07 am -
1 stop7h 36m
Deal found 8/30![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:27 pm -
2 stops25h 51m
Deal found 8/29![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:12 am -
1 stop15h 41m
Deal found 8/29![Frontier logo]()
$121
This Trip.com deal was found by Cheapflights users on 8/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:30 am -
1 stop17h 29m
Deal found 8/31![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:27 pm -
1 stop21h 12m
Deal found 8/30![Frontier logo]()
$124
This Trip.com deal was found by Cheapflights users on 8/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:13 pm -
1 stop19h 21m
Deal found 8/30![Frontier logo]()
$134
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 2, 2026.
Round-trip from | $207 (Kiwi.com) |
|---|---|
One-way from | $110 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $325 |
Good round-trip deal | $298 or less |
Good one-way deal | $134 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 2, 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
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Tue 11/10
11:40 am-12:45 am
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Tue 11/17
5:50 pm-10:55 pm
1 stop6h 05m
$295
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Thu 10/29
3:25 pm-1:25 am
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Sun 11/1
6:05 am-6:15 pm
1 stop13h 10m
$295
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Mon 10/26
5:05 pm-1:25 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Fri 10/30
6:00 am-6:15 pm
1 stop12h 15m
$295
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Sat 10/17
8:00 am-11:51 am
Nonstop3h 51m
San Juan Luis Munoz Marin Intl
Tue 10/20
5:50 pm-9:41 pm
Nonstop3h 51m
$297
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Mon 9/14
6:30 am-3:42 pm
1 stop9h 12m
San Juan Luis Munoz Marin Intl
Wed 9/16
1:00 am-8:57 am
1 stop7h 57m
$306
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Sat 9/5
11:45 am-6:20 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Fri 9/11
5:45 pm-11:55 pm
1 stop6h 10m
$315
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Sat 9/19
8:15 am-7:25 pm
2 stops11h 10m
San Juan Luis Munoz Marin Intl
Sat 9/26
6:25 am-3:55 pm
1 stop9h 30m
$326
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Tue 11/3
1:00 pm-12:45 am
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Tue 11/10
5:40 am-2:55 pm
2 stops10h 15m
$326
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sat 9/12
7:00 am-1:45 pm
1 stop6h 45m
San Juan Luis Munoz Marin Intl
Wed 9/16
1:25 pm-9:00 pm
1 stop7h 35m
$331
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Sat 10/24
10:58 am-8:38 pm
1 stop9h 40m
San Juan Luis Munoz Marin Intl
Sat 10/24
1:05 am-10:24 am
1 stop9h 19m
$341
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.
RDU-SJU
IAD-SJU
IAD-MBJ
IAD-AUA
DCA-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
RDU-SJU
IAD-SJU
IAD-MBJ
IAD-AUA
What is the cheapest month to book a flight from Virginia to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $449). Flying from Virginia to Caribbean in December is currently the most expensive (average of $619). 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 September 2, 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 61 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.
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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 2, 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$530 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$532 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$620 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$219 | Average$549 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$252 | Average$623 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |