$100+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Sep 12 — Sep 191
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 August 13, 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 August 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Fri 9/117:33 pm -
2 stops21h 30m
Fri 9/182:51 pm -
1 stop18h 49m
Deal found 8/12![Multiple Airlines logo]()
$232
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:15 pm -
Nonstop3h 44m
Thu 9/31:48 pm -
1 stop7h 31m
Deal found 8/11![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Thu 8/278:57 pm -
1 stop11h 21m
Deal found 8/10![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:46 pm -
1 stop26h 12m
Thu 10/14:39 pm -
1 stop23h 15m
Deal found 8/10![Multiple Airlines logo]()
$236
This CheapOair deal was found by Cheapflights users on 8/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:15 pm -
Nonstop3h 44m
Wed 8/263:22 pm -
Nonstop3h 39m
Deal found 8/12![Multiple Airlines logo]()
$237
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Tue 8/253:22 pm -
Nonstop3h 39m
Deal found 8/11![Multiple Airlines logo]()
$238
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:44 pm -
Nonstop3h 40m
Thu 9/33:28 pm -
Nonstop3h 52m
Deal found 8/11![Multiple Airlines logo]()
$239
This Super.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:15 pm -
Nonstop3h 44m
Sun 9/63:28 pm -
Nonstop3h 52m
Deal found 8/10![Frontier logo]()
$240
This Super.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Sun 8/233:28 pm -
Nonstop3h 52m
Deal found 8/10![Frontier logo]()
$241
This eDestinos deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Mon 8/247:30 am -
1 stop10h 22m
Deal found 8/10![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:49 pm -
1 stop7h 09m
Sun 9/137:00 am -
1 stop6h 59m
Deal found 8/11![Frontier logo]()
$244
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:14 am -
1 stop8h 36m
Sat 9/193:41 pm -
1 stop7h 10m
Deal found 8/12![American Airlines logo]()
$296
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 August 13, 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 August 13, 2026.
This JetBlue deal was found by Cheapflights users on 8/12. 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.
Mon 11/92:00 pm -
1 stop8h 04m
Thu 11/196:01 am -
Nonstop3h 39m
Deal found 8/12![JetBlue logo]()
$274
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:50 pm -
1 stop8h 15m
Wed 9/21:20 pm -
2 stops9h 45m
Deal found 8/11![Southwest logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:30 am -
2 stops13h 20m
Fri 10/231:00 am -
2 stops13h 23m
Deal found 8/10![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:54 pm -
1 stop7h 35m
Sat 8/292:31 pm -
1 stop8h 55m
Deal found 8/11![Delta logo]()
$386
This American Airlines deal was found by Cheapflights users on 8/7. Clicking the “Pick Dates” 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 9/266:14 am -
1 stop7h 24m
Wed 9/302:39 pm -
1 stop8h 12m
Deal found 8/7![American Airlines logo]()
$466
This Copa Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:25 am -
1 stop9h 07m
Mon 10/1212:43 pm -
1 stop15h 37m
Deal found 8/11![Copa Airlines logo]()
$536
This JetBlue deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:56 pm -
Nonstop3h 38m
Mon 8/317:00 am -
1 stop6h 05m
Deal found 8/10![JetBlue logo]()
$288
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:40 pm -
1 stop8h 25m
Mon 11/26:05 am -
1 stop6h 10m
Deal found 8/11![Southwest logo]()
$320
This JetBlue deal was found by Cheapflights users on 8/12. 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 11/85:35 pm -
Nonstop3h 22m
Thu 11/196:00 am -
1 stop8h 00m
Deal found 8/12![JetBlue logo]()
$307
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:00 pm -
2 stops10h 10m
Tue 9/298:20 am -
1 stop7h 45m
Deal found 8/11![Southwest logo]()
$321
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 9/109:00 am -
Nonstop3h 54m
Tue 9/153:56 pm -
1 stop8h 48m
Deal found 8/12![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 8/12. 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.
Fri 9/255:05 pm -
1 stop6h 50m
Wed 9/301:20 pm -
2 stops9h 45m
Deal found 8/12![Southwest logo]()
$321
This JetBlue deal was found by Cheapflights users on 8/12. 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.
Mon 9/218:00 am -
Nonstop3h 52m
Tue 9/296:07 pm -
Nonstop3h 51m
Deal found 8/12![JetBlue logo]()
$342
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:15 am -
2 stops14h 09m
Mon 11/162:05 am -
1 stop7h 40m
Deal found 8/12![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:20 pm -
2 stops9h 30m
Fri 10/236:30 am -
2 stops10h 10m
Deal found 8/10![Southwest logo]()
$346
This Delta deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am -
1 stop5h 55m
Sat 11/142:55 pm -
1 stop6h 50m
Deal found 8/11![Delta logo]()
$466
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Thu 9/179:00 am -
Nonstop3h 54m
Sun 9/201:00 am -
1 stop6h 19m
Deal found 8/12![United Airlines logo]()
$396
This JetBlue deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:00 am -
Nonstop3h 51m
Sat 11/76:50 pm -
Nonstop3h 57m
Deal found 8/12![JetBlue logo]()
$377
This Delta deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am -
1 stop5h 50m
Wed 10/283:19 pm -
1 stop4h 55m
Deal found 8/10![Delta logo]()
$476
This Southwest deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 10/2810:35 am -
2 stops9h 55m
Sat 11/710:55 am -
1 stop8h 15m
Deal found 8/8![Southwest logo]()
$361
This United Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:40 am -
Nonstop3h 54m
Sun 10/184:55 pm -
Nonstop3h 52m
Deal found 8/12![United Airlines logo]()
$404
This Copa Airlines deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/254:34 pm -
1 stop19h 43m
Wed 9/3012:22 pm -
1 stop14h 58m
Deal found 8/10![Copa Airlines logo]()
$563
This JetBlue deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop5h 30m
Mon 11/212:25 pm -
1 stop11h 09m
Deal found 8/10![JetBlue logo]()
$396
This Southwest deal was found by Cheapflights users on 8/12. 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.
Sat 8/298:15 am -
2 stops9h 50m
Fri 9/1110:00 am -
2 stops9h 40m
Deal found 8/12![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 1/298:15 pm -
1 stop15h 15m
Wed 2/35:45 pm -
1 stop17h 20m
Deal found 8/8![Delta logo]()
$512
This United Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:15 am -
1 stop8h 29m
Wed 9/304:55 pm -
Nonstop3h 52m
Deal found 8/11![United Airlines logo]()
$428
This JetBlue deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop6h 12m
Tue 10/203:00 pm -
1 stop8h 40m
Deal found 8/9![JetBlue logo]()
$396
This Delta deal was found by Cheapflights users on 8/8. Clicking the “Pick Dates” 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 1/276:05 am -
1 stop6h 25m
Sat 1/306:06 pm -
1 stop16h 06m
Deal found 8/8![Delta logo]()
$512
This Copa Airlines deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:37 pm -
1 stop22h 04m
Mon 11/167:10 am -
1 stop17h 23m
Deal found 8/9![Copa Airlines logo]()
$621
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:51 pm -
1 stop13h 59m
Sat 10/1711:50 am -
1 stop12h 38m
Deal found 8/12![American Airlines logo]()
$692
Last-minute flights from Virginia to CaribbeanDiscover last-minute flight deals from Virginia to Caribbean. Data last updated August 13, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia to Caribbean. Data last updated August 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Thu 8/278:57 pm -
1 stop11h 21m
Deal found 8/10![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Tue 8/253:22 pm -
Nonstop3h 39m
Deal found 8/11![Multiple Airlines logo]()
$238
This Super.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Sun 8/233:28 pm -
Nonstop3h 52m
Deal found 8/10![Frontier logo]()
$241
This eDestinos deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm -
Nonstop3h 44m
Mon 8/247:30 am -
1 stop10h 22m
Deal found 8/10![Frontier logo]()
$242
This CheapOair deal was found by Cheapflights users on 8/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:15 pm -
Nonstop3h 44m
Wed 8/263:22 pm -
Nonstop3h 39m
Deal found 8/12![Multiple Airlines logo]()
$237
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:44 pm -
Nonstop3h 40m
Thu 9/33:28 pm -
Nonstop3h 52m
Deal found 8/11![Multiple Airlines logo]()
$239
This Priceline deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/308:15 pm -
Nonstop3h 44m
Thu 9/31:48 pm -
1 stop7h 31m
Deal found 8/11![Multiple Airlines logo]()
$233
This Super.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:15 pm -
Nonstop3h 44m
Sun 9/63:28 pm -
Nonstop3h 52m
Deal found 8/10![Frontier logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Fri 9/117:33 pm -
2 stops21h 30m
Fri 9/182:51 pm -
1 stop18h 49m
Deal found 8/12![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:49 pm -
1 stop7h 09m
Sun 9/137:00 am -
1 stop6h 59m
Deal found 8/11![Frontier logo]()
$244
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:57 am -
1 stop6h 53m
Tue 9/153:41 pm -
1 stop7h 10m
Deal found 8/12![American Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:46 pm -
1 stop26h 12m
Thu 10/14:39 pm -
1 stop23h 15m
Deal found 8/10![Multiple Airlines logo]()
$236
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 August 13, 2026.
Search for one-way flight options from Virginia to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 13, 2026.
This Super.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:35 am -
1 stop6h 07m
Deal found 8/9![JetBlue logo]()
$100
This Super.com deal was found by Cheapflights users on 8/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:35 am -
1 stop6h 23m
Deal found 8/12![JetBlue logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:35 am -
1 stop26h 59m
Deal found 8/10![Frontier logo]()
$115
This Super.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:35 am -
1 stop6h 07m
Deal found 8/11![JetBlue logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/3012:05 pm -
1 stop29h 43m
Deal found 8/11![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop5h 30m
Deal found 8/9![JetBlue logo]()
$117
This Flightnetwork deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/133:45 pm -
1 stop21h 50m
Deal found 8/9![Air Canada logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:55 pm -
1 stop6h 39m
Deal found 8/9![Frontier logo]()
$118
This Flightnetwork deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/134:20 pm -
1 stop21h 15m
Deal found 8/9![Air Canada logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:49 pm -
1 stop7h 09m
Deal found 8/11![Frontier logo]()
$119
This Travelocity deal was found by Cheapflights users on 8/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:45 pm -
1 stop21h 50m
Deal found 8/10![Air Canada logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:35 pm -
1 stop16h 43m
Deal found 8/9![Frontier logo]()
$120
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 August 13, 2026.
Round-trip from | $232 (Kiwi.com) |
|---|---|
One-way from | $100 (Super.com) |
Popular in | December |
Cheapest in | September |
Average price | $347 |
Good round-trip deal | $277 or less |
Good one-way deal | $140 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 2,558,603 searches. Data last updated August 13, 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
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Mon 11/9
2:00 pm-11:04 pm
1 stop8h 04m
San Juan Luis Munoz Marin Intl
Thu 11/19
6:01 am-8:40 am
Nonstop3h 39m
$274
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Fri 8/28
7:56 pm-11:34 pm
Nonstop3h 38m
San Juan Luis Munoz Marin Intl
Mon 8/31
7:00 am-1:05 pm
1 stop6h 05m
$288
RaleighSan Juan
RDU Raleigh-Durham - SJU San Juan Luis Munoz Marin Intl
RDUSJU
Raleigh-Durham
Sun 11/8
5:35 pm-9:57 pm
Nonstop3h 22m
San Juan Luis Munoz Marin Intl
Thu 11/19
6:00 am-1:00 pm
1 stop8h 00m
$307
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Wed 8/26
12:50 pm-9:05 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Wed 9/2
1:20 pm-11:05 pm
2 stops9h 45m
$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
Thu 10/29
2:40 pm-11:05 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Mon 11/2
6:05 am-11:15 am
1 stop6h 10m
$320
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 9/24
1:00 pm-11:10 pm
2 stops10h 10m
San Juan Luis Munoz Marin Intl
Tue 9/29
8:20 am-4:05 pm
1 stop7h 45m
$321
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Fri 9/25
5:05 pm-11:55 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Wed 9/30
1:20 pm-11:05 pm
2 stops9h 45m
$321
Quickest 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
Mon 9/21
8:00 am-11:52 am
Nonstop3h 52m
San Juan Luis Munoz Marin Intl
Tue 9/29
6:07 pm-9:58 pm
Nonstop3h 51m
$342
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 10/20
12:20 pm-9:50 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Fri 10/23
6:30 am-4:40 pm
2 stops10h 10m
$346
Washington, D.C.San Juan
DCA Washington, D.C. Reagan-National - SJU San Juan Luis Munoz Marin Intl
DCASJU
Washington, D.C. Reagan-National
Wed 10/28
10:35 am-8:30 pm
2 stops9h 55m
San Juan Luis Munoz Marin Intl
Sat 11/7
10:55 am-6:10 pm
1 stop8h 15m
$361
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-NAS
DCA-NAS
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-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 $449). Flying from Virginia to Caribbean in December is currently the most expensive (average of $618). 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 August 13, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia to Caribbean as you normally would.
How far ahead should I book a flight from Virginia to Caribbean?
The price you pay for your flight from Virginia to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Related info for your journey
Find useful and relevant information for your journey from Virginia to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top countries
Top destinations
Alternative routes for Virginia to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Virginia to Caribbean by cabin class
Find flights from Virginia to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Virginia and Caribbean flights
Browse other Virginia and Caribbean flight options. Last updated on August 13, 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 2,558,603 searches. Data last updated August 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$379 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$514 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$594 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$542 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$237 | Average$618 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |