$104+ Cheap flights from Virginia to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 17 — Oct 241
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 17, 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 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:07 am -
1 stop17h 52m
Fri 11/133:59 pm -
1 stop8h 58m
Deal found 9/13![Frontier logo]()
$206
This FlightHub deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/612:58 pm -
1 stop11h 01m
Wed 11/113:59 pm -
1 stop8h 58m
Deal found 9/14![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:30 am -
1 stop9h 36m
Tue 10/2712:59 am -
1 stop10h 03m
Deal found 9/13![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:05 pm -
1 stop10h 45m
Wed 11/183:59 pm -
1 stop8h 58m
Deal found 9/12![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/104:20 pm -
1 stop7h 39m
Fri 11/1312:59 am -
1 stop9h 12m
Deal found 9/12![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:55 pm -
2 stops18h 24m
Mon 10/265:11 pm -
1 stop7h 17m
Deal found 9/13![Frontier logo]()
$216
This Priceline deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:26 pm -
1 stop24h 11m
Sat 10/245:11 pm -
1 stop7h 17m
Deal found 9/12![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:35 am -
1 stop8h 44m
Mon 10/1912:59 am -
2 stops14h 22m
Deal found 9/13![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:26 pm -
1 stop8h 27m
Wed 10/215:11 pm -
1 stop7h 17m
Deal found 9/13![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:30 am -
1 stop9h 36m
Mon 10/262:58 am -
1 stop6h 19m
Deal found 9/13![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:07 am -
1 stop7h 36m
Mon 10/125:11 pm -
1 stop7h 17m
Deal found 9/13![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:30 pm -
2 stops26h 29m
Tue 11/177:26 pm -
1 stop14h 41m
Deal found 9/14![Frontier logo]()
$222
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 17, 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 17, 2026.
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/185:30 pm -
Nonstop3h 32m
Thu 10/226:10 am -
1 stop7h 01m
Deal found 9/13![JetBlue logo]()
$289
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:40 pm -
1 stop6h 10m
Tue 10/275:05 am -
1 stop6h 35m
Deal found 9/15![Southwest logo]()
$325
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:29 pm -
Nonstop3h 53m
Tue 11/178:05 am -
Nonstop4h 04m
Deal found 9/16![United Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1412:35 pm -
1 stop10h 24m
Thu 12/176:59 pm -
1 stop6h 43m
Deal found 9/12![Delta logo]()
$366
This Copa Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/191:19 am -
1 stop12h 09m
Sat 2/2712:18 pm -
1 stop14h 58m
Deal found 9/13![Copa Airlines logo]()
$469
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/34:55 pm -
1 stop7h 18m
Mon 11/95:30 pm -
1 stop6h 54m
Deal found 9/14![JetBlue logo]()
$310
This United deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:56 am -
Nonstop4h 00m
Fri 12/1112:57 pm -
2 stops10h 57m
Deal found 9/13![Multiple Airlines logo]()
$669
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:45 am -
1 stop7h 00m
Thu 10/224:55 pm -
Nonstop3h 52m
Deal found 9/16![United Airlines logo]()
$342
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:30 pm -
Nonstop3h 32m
Mon 10/196:10 am -
1 stop7h 01m
Deal found 9/13![JetBlue logo]()
$311
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:25 am -
1 stop6h 50m
Tue 10/2012:40 pm -
2 stops9h 15m
Deal found 9/15![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/73:00 pm -
1 stop7h 13m
Sun 12/137:00 am -
1 stop10h 03m
Deal found 9/14![Delta logo]()
$366
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:05 pm -
1 stop7h 31m
Fri 10/306:40 am -
2 stops12h 35m
Deal found 9/16![United Airlines logo]()
$346
This JetBlue deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:10 pm -
1 stop6h 34m
Fri 12/47:00 pm -
Nonstop3h 58m
Deal found 9/14![JetBlue logo]()
$319
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/319:35 am -
2 stops10h 35m
Mon 11/25:35 am -
2 stops11h 05m
Deal found 9/16![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/208:00 am -
1 stop8h 20m
Sat 1/236:15 am -
1 stop9h 23m
Deal found 9/12![Delta logo]()
$366
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:30 pm -
Nonstop3h 27m
Wed 11/116:25 am -
1 stop7h 38m
Deal found 9/13![JetBlue logo]()
$320
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/18:22 am -
Nonstop3h 53m
Fri 12/48:05 am -
Nonstop4h 04m
Deal found 9/14![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:00 pm -
1 stop5h 50m
Sun 12/66:05 am -
2 stops8h 15m
Deal found 9/12![Southwest logo]()
$386
This Copa Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/132:25 am -
1 stop9h 52m
Sun 10/1812:22 pm -
1 stop14h 58m
Deal found 9/16![Copa Airlines logo]()
$488
This United Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/75:29 pm -
Nonstop3h 53m
Mon 11/98:25 am -
1 stop9h 59m
Deal found 9/15![United Airlines logo]()
$383
This JetBlue deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:54 pm -
1 stop8h 19m
Fri 11/136:50 pm -
Nonstop3h 56m
Deal found 9/13![JetBlue logo]()
$357
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/105:10 pm -
1 stop6h 45m
Tue 10/135:05 am -
2 stops8h 00m
Deal found 9/13![Southwest logo]()
$396
This Copa Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/181:19 am -
1 stop16h 10m
Tue 2/233:39 pm -
1 stop12h 37m
Deal found 9/15![Copa Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/126:00 am -
1 stop7h 45m
Sat 10/171:00 am -
1 stop6h 49m
Deal found 9/12![United Airlines logo]()
$391
This JetBlue deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop7h 05m
Mon 11/165:30 pm -
1 stop6h 54m
Deal found 9/16![JetBlue logo]()
$361
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:45 am -
1 stop7h 55m
Sun 12/66:05 am -
2 stops8h 15m
Deal found 9/16![Southwest logo]()
$404
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
1 stop9h 45m
Sun 1/106:00 pm -
1 stop15h 08m
Deal found 9/14![Delta logo]()
$503
This Copa Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/91:16 am -
1 stop10h 02m
Sun 11/1512:17 pm -
1 stop11h 16m
Deal found 9/15![Copa Airlines logo]()
$508
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:56 am -
Nonstop4h 00m
Mon 11/163:00 pm -
1 stop8h 25m
Deal found 9/16![United Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2711:35 am -
1 stop11h 00m
Sat 12/56:45 am -
2 stops10h 05m
Deal found 9/13![Southwest logo]()
$406
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated September 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:35 am -
1 stop8h 44m
Mon 10/1912:59 am -
2 stops14h 22m
Deal found 9/13![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:07 am -
1 stop7h 36m
Mon 10/125:11 pm -
1 stop7h 17m
Deal found 9/13![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:08 pm -
1 stop7h 01m
Wed 10/215:11 pm -
1 stop7h 17m
Deal found 9/12![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:30 am -
1 stop9h 36m
Tue 10/2712:59 am -
1 stop10h 03m
Deal found 9/13![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:30 am -
1 stop9h 36m
Mon 10/262:58 am -
1 stop6h 19m
Deal found 9/13![Frontier logo]()
$220
This Priceline deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:26 pm -
1 stop24h 11m
Sat 10/245:11 pm -
1 stop7h 17m
Deal found 9/12![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:26 pm -
1 stop8h 27m
Wed 10/215:11 pm -
1 stop7h 17m
Deal found 9/13![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:07 am -
1 stop7h 30m
Fri 10/303:59 pm -
1 stop7h 58m
Deal found 9/15![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/239:30 pm -
2 stops18h 36m
Thu 10/293:59 pm -
1 stop20h 04m
Deal found 9/15![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/243:55 pm -
2 stops18h 24m
Mon 10/265:11 pm -
1 stop7h 17m
Deal found 9/13![Frontier logo]()
$216
This JetBlue deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am -
1 stop7h 04m
Wed 10/284:30 pm -
1 stop6h 54m
Deal found 9/12![JetBlue logo]()
$225
This FlightHub deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:45 pm -
1 stop11h 05m
Tue 11/33:59 pm -
1 stop7h 50m
Deal found 9/13![Frontier logo]()
$225
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 17, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1612:58 pm -
1 stop11h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:12 am -
1 stop15h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:16 pm -
2 stops27h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/149:53 pm -
1 stop12h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1312:58 pm -
2 stops26h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3012:58 pm -
2 stops27h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:30 pm -
1 stop11h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$114
This Priceline deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:26 pm -
1 stop15h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/13![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:05 pm -
1 stop8h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Frontier logo]()
$116
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/318:56 am -
Nonstop4h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$129
This United Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop9h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$133
This JetBlue deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/87:00 am -
1 stop6h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![JetBlue logo]()
$138
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 17, 2026.
Round-trip from | $206 (Kiwi.com) |
|---|---|
One-way from | $104 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $310 |
Good round-trip deal | $273 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 17, 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.Saint Thomas Island
IAD Washington, D.C. Dulles Intl - STT Saint Thomas Island Cyril E King
IADSTT
Washington, D.C. Dulles Intl
Thu 12/31
8:56 am-1:56 pm
Nonstop4h 00m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$129
Washington, D.C.Montego Bay
DCA Washington, D.C. Reagan-National - MBJ Montego Bay Sangster Intl
DCAMBJ
Washington, D.C. Reagan-National
Sun 10/4
7:05 am-12:10 pm
1 stop6h 05m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$139
Washington, D.C.Montego Bay
DCA Washington, D.C. Reagan-National - MBJ Montego Bay Sangster Intl
DCAMBJ
Washington, D.C. Reagan-National
Sat 10/24
7:07 am-12:06 pm
1 stop5h 59m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$144
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Sun 11/8
3:25 pm-11:35 pm
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
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 10/5
5:35 pm-12:25 am
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$153
Washington, D.C.Oranjestad
DCA Washington, D.C. Reagan-National - AUA Oranjestad Reina Beatrix
DCAAUA
Washington, D.C. Reagan-National
Wed 12/9
12:55 pm-4:30 pm
2 stops26h 35m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$155
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Mon 10/5
1:56 pm-2:13 am
2 stops12h 17m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sat 12/5
1:50 pm-8:55 pm
1 stop6h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$161
Quickest round-trip
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sat 11/14
7:30 pm-11:57 pm
Nonstop3h 27m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sun 11/15
7:30 pm-11:57 pm
Nonstop3h 27m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$164
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
DCA-SJU
IAD-SJU
IAD-MBJ
IAD-STT
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia to Caribbean
USVA-0CB
RDU-SJU
DCA-SJU
IAD-SJU
IAD-MBJ
What is the cheapest month to book a flight from Virginia to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $455). Flying from Virginia to Caribbean in December is currently the most expensive (average of $615). 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 59 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 September 17, 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 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$379 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$525 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$542 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$543 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$212 | Average$614 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$245 | Average$622 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |