$130+ Cheap flights from Virginia Beach, VA 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Sep 7 — Sep 141
Round-trip
1 adult, Economy
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Find cheap flights from Virginia Beach 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
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Cheapest flights from Virginia Beach to CaribbeanExplore the most affordable flight options available from Virginia Beach to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
Explore the most affordable flight options available from Virginia Beach to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:18 pm -
2 stops12h 55m
Tue 9/296:05 pm -
1 stop28h 24m
Deal found 8/8![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
2 stops32h 17m
Sat 9/269:30 am -
1 stop12h 59m
Deal found 8/4![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:39 pm -
2 stops26h 38m
Mon 9/214:39 pm -
1 stop25h 04m
Deal found 8/4![Multiple Airlines logo]()
$271
This Cheapflightsfares deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:13 pm -
Nonstop3h 22m
Wed 8/2611:06 am -
Nonstop3h 34m
Deal found 8/4![JetBlue logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am -
1 stop6h 53m
Wed 9/168:45 am -
2 stops13h 44m
Deal found 8/4![Multiple Airlines logo]()
$274
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:35 pm -
Nonstop3h 23m
Sun 8/2311:44 am -
Nonstop3h 34m
Deal found 8/4![JetBlue logo]()
$275
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:43 pm -
1 stop6h 09m
Wed 9/1610:42 am -
1 stop8h 06m
Deal found 8/4![Frontier logo]()
$276
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:30 pm -
Nonstop3h 32m
Sun 10/189:00 am -
Nonstop3h 22m
Deal found 8/8![JetBlue logo]()
$278
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:20 pm -
2 stops11h 36m
Thu 9/33:10 am -
1 stop13h 01m
Deal found 8/7![Frontier logo]()
$281
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop6h 50m
Tue 11/32:52 pm -
2 stops19h 51m
Deal found 8/7![United Airlines logo]()
$354
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.
Sun 11/87:20 pm -
1 stop14h 10m
Fri 11/132:18 pm -
1 stop9h 40m
Deal found 8/7![American Airlines logo]()
$368
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.
Wed 11/46:00 am -
1 stop7h 43m
Tue 11/102:44 pm -
1 stop8h 54m
Deal found 8/7![American Airlines logo]()
$373
Best flights from Virginia Beach to CaribbeanDiscover carefully curated flight deals from Virginia Beach to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
Discover carefully curated flight deals from Virginia Beach to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/91:30 pm -
Nonstop3h 32m
Sun 10/189:00 am -
Nonstop3h 22m
Deal found 8/8![JetBlue logo]()
$278
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:02 am -
1 stop7h 43m
Sun 9/131:00 am -
1 stop8h 53m
Deal found 8/4![United Airlines logo]()
$284
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/135:30 am -
1 stop6h 15m
Tue 9/227:30 am -
1 stop9h 25m
Deal found 8/4![Delta logo]()
$284
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/36:55 am -
1 stop7h 55m
Mon 2/85:35 am -
1 stop6h 30m
Deal found 8/7![Southwest logo]()
$309
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:00 am -
1 stop6h 15m
Sat 10/243:02 pm -
1 stop8h 34m
Deal found 8/3![American Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 10/176:15 am -
1 stop6h 19m
Fri 10/231:00 am -
2 stops11h 15m
Deal found 8/6![United Airlines logo]()
$284
This JetBlue deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/91:20 pm -
Nonstop3h 32m
Fri 9/112:32 pm -
1 stop8h 09m
Deal found 8/6![JetBlue logo]()
$303
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/214:13 pm -
1 stop22h 44m
Fri 8/288:39 am -
2 stops12h 30m
Deal found 8/3![Multiple Airlines logo]()
$617
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:15 am -
1 stop6h 39m
Mon 9/211:00 am -
2 stops8h 41m
Deal found 8/4![United Airlines logo]()
$284
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:15 am -
2 stops14h 50m
Wed 11/113:46 pm -
2 stops18h 57m
Deal found 8/7![Copa Airlines logo]()
$637
This JetBlue deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 11/61:30 pm -
Nonstop3h 24m
Fri 11/1310:00 am -
Nonstop3h 32m
Deal found 8/5![JetBlue logo]()
$335
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/133:15 pm -
2 stops9h 20m
Tue 9/228:20 am -
2 stops9h 00m
Deal found 8/4![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:30 am -
1 stop6h 20m
Fri 11/131:00 pm -
1 stop8h 37m
Deal found 8/6![Delta logo]()
$408
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/37:18 pm -
2 stops16h 49m
Mon 12/71:09 pm -
2 stops9h 01m
Deal found 8/3![American Airlines logo]()
$428
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop6h 50m
Tue 11/32:52 pm -
2 stops19h 51m
Deal found 8/7![United Airlines logo]()
$354
This JetBlue deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/44:35 pm -
1 stop7h 19m
Wed 9/99:00 am -
Nonstop3h 22m
Deal found 8/5![JetBlue logo]()
$363
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:30 am -
1 stop10h 00m
Sat 12/52:55 pm -
1 stop6h 18m
Deal found 8/7![Delta logo]()
$411
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:00 am -
1 stop5h 30m
Tue 12/151:18 pm -
2 stops8h 52m
Deal found 8/3![American Airlines logo]()
$428
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:45 pm -
2 stops8h 10m
Sun 9/206:35 am -
2 stops9h 25m
Deal found 8/7![Southwest logo]()
$430
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:02 am -
1 stop7h 31m
Mon 9/142:35 pm -
2 stops9h 08m
Deal found 8/8![United Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am -
2 stops8h 18m
Mon 8/311:27 pm -
1 stop9h 41m
Deal found 8/3![American Airlines logo]()
$428
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am -
1 stop11h 06m
Wed 9/92:53 pm -
1 stop9h 42m
Deal found 8/4![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/248:00 pm -
2 stops15h 53m
Wed 2/1012:55 pm -
2 stops10h 41m
Deal found 8/5![United Airlines logo]()
$388
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/82:00 pm -
2 stops7h 16m
Fri 11/132:18 pm -
1 stop9h 40m
Deal found 8/8![American Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:30 am -
1 stop8h 10m
Wed 11/44:05 pm -
1 stop9h 40m
Deal found 8/4![Delta logo]()
$458
This JetBlue deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:00 am -
1 stop8h 48m
Thu 10/291:00 pm -
1 stop7h 00m
Deal found 8/3![JetBlue logo]()
$462
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:15 am -
2 stops14h 23m
Mon 10/261:35 pm -
2 stops10h 09m
Deal found 8/8![United Airlines logo]()
$399
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.
Tue 9/226:00 am -
1 stop9h 17m
Tue 9/292:15 pm -
1 stop8h 14m
Deal found 8/7![American Airlines logo]()
$446
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:23 am -
1 stop8h 05m
Tue 9/152:53 pm -
1 stop9h 42m
Deal found 8/3![Delta logo]()
$458
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:25 am -
1 stop5h 54m
Fri 9/253:59 pm -
1 stop6h 42m
Deal found 8/4![JetBlue logo]()
$464
Last-minute flights from Virginia Beach to CaribbeanDiscover last-minute flight deals from Virginia Beach to Caribbean. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Caribbean. Data last updated August 8, 2026 and is based on user searches.
This JetBlue deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/193:35 pm -
Nonstop3h 23m
Sun 8/2311:44 am -
Nonstop3h 34m
Deal found 8/4![JetBlue logo]()
$275
This Cheapflightsfares deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:13 pm -
Nonstop3h 22m
Wed 8/2611:06 am -
Nonstop3h 34m
Deal found 8/4![JetBlue logo]()
$273
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:20 pm -
2 stops11h 36m
Sat 9/58:45 am -
1 stop24h 46m
Deal found 8/7![Multiple Airlines logo]()
$278
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:20 pm -
2 stops11h 36m
Thu 9/33:10 am -
1 stop13h 01m
Deal found 8/7![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am -
1 stop6h 53m
Wed 9/168:45 am -
2 stops13h 44m
Deal found 8/4![Multiple Airlines logo]()
$274
This Frontier deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:43 pm -
1 stop6h 09m
Wed 9/1610:42 am -
1 stop8h 06m
Deal found 8/4![Frontier logo]()
$276
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:02 am -
1 stop7h 31m
Mon 9/142:35 pm -
1 stop8h 19m
Deal found 8/8![United Airlines logo]()
$376
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.
Wed 9/95:30 am -
1 stop8h 08m
Mon 9/1412:34 pm -
1 stop11h 22m
Deal found 8/7![American Airlines logo]()
$381
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:39 pm -
2 stops26h 38m
Mon 9/214:39 pm -
1 stop25h 04m
Deal found 8/4![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/217:00 am -
2 stops32h 17m
Sat 9/269:30 am -
1 stop12h 59m
Deal found 8/4![Multiple Airlines logo]()
$269
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.
Mon 9/215:30 am -
2 stops7h 56m
Mon 9/2812:34 pm -
1 stop11h 22m
Deal found 8/7![American Airlines logo]()
$380
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/241:18 pm -
2 stops12h 55m
Tue 9/296:05 pm -
1 stop28h 24m
Deal found 8/8![Multiple Airlines logo]()
$266
One-way flights from Virginia Beach to CaribbeanSearch for one-way flight options from Virginia Beach to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
Search for one-way flight options from Virginia Beach to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
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 12/127:29 pm -
1 stop14h 50m
Deal found 8/7![American Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 9/81:20 pm -
2 stops36h 53m
Deal found 8/6![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:20 am -
1 stop16h 36m
Deal found 8/4![Multiple Airlines logo]()
$131
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/11:18 pm -
2 stops34h 40m
Deal found 8/8![Frontier logo]()
$134
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/41:18 pm -
2 stops34h 40m
Deal found 8/7![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:30 pm -
1 stop19h 16m
Deal found 8/4![Multiple Airlines logo]()
$137
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.
Thu 11/127:20 pm -
1 stop14h 10m
Deal found 8/7![American Airlines logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:00 am -
1 stop8h 45m
Deal found 8/4![Multiple Airlines logo]()
$138
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1012:57 pm -
2 stops29h 22m
Deal found 8/7![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/5. Clicking the “Pick Dates” 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 9/21:20 pm -
2 stops35h 14m
Deal found 8/5![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/512:57 pm -
2 stops35h 00m
Deal found 8/4![Frontier logo]()
$142
This United Airlines deal was found by Cheapflights users on 8/6. Clicking the “Pick Dates” 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 12/126:00 am -
1 stop9h 03m
Deal found 8/6![United Airlines logo]()
$146
Find flight deals from Virginia Beach to Caribbean
Keep the following information in mind while searching for Virginia Beach to Caribbean flight deals. Data was last updated August 8, 2026.
Round-trip from | $266 (Kiwi.com) |
|---|---|
One-way from | $130 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $350 |
Cheapflights Fare Finder
Customize your flight search to find flights from Virginia Beach 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 8, 2026.
Use the filters below to find and compare flights from Virginia Beach to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Fri 10/9
1:30 pm-5:02 pm
Nonstop3h 32m
San Juan Luis Munoz Marin Intl
Sun 10/18
9:00 am-12:22 pm
Nonstop3h 22m
$278
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Fri 9/11
6:02 am-1:45 pm
1 stop7h 43m
San Juan Luis Munoz Marin Intl
Sun 9/13
1:00 am-9:53 am
1 stop8h 53m
$284
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Sun 9/13
5:30 am-11:45 am
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Tue 9/22
7:30 am-4:55 pm
1 stop9h 25m
$284
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Sat 10/17
6:15 am-12:34 pm
1 stop6h 19m
San Juan Luis Munoz Marin Intl
Fri 10/23
1:00 am-12:15 pm
2 stops11h 15m
$284
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Sun 9/13
6:15 am-12:54 pm
1 stop6h 39m
San Juan Luis Munoz Marin Intl
Mon 9/21
1:00 am-9:41 am
2 stops8h 41m
$284
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Wed 9/9
1:20 pm-4:52 pm
Nonstop3h 32m
San Juan Luis Munoz Marin Intl
Fri 9/11
2:32 pm-10:41 pm
1 stop8h 09m
$303
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Wed 2/3
6:55 am-3:50 pm
1 stop7h 55m
San Juan Luis Munoz Marin Intl
Mon 2/8
5:35 am-11:05 am
1 stop6h 30m
$309
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Fri 11/6
1:30 pm-5:54 pm
Nonstop3h 24m
San Juan Luis Munoz Marin Intl
Fri 11/13
10:00 am-12:32 pm
Nonstop3h 32m
$335
NorfolkSimpson Bay
ORF Norfolk - SXM Simpson Bay Princess Juliana
ORFSXM
Norfolk
Thu 10/29
6:00 am-12:50 pm
1 stop6h 50m
Simpson Bay Princess Juliana
Tue 11/3
2:52 pm-9:43 am
2 stops19h 51m
$354
NorfolkSan Juan
ORF Norfolk - SJU San Juan Luis Munoz Marin Intl
ORFSJU
Norfolk
Fri 9/4
4:35 pm-11:54 pm
1 stop7h 19m
San Juan Luis Munoz Marin Intl
Wed 9/9
9:00 am-12:22 pm
Nonstop3h 22m
$363
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Virginia Beach to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Virginia Beach with our price prediction graph.
ORF-NAS
ORF-SJU
ORF-PUJ
ORF-SDQ
ORF-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Virginia Beach to Caribbean
V1B-0CB
ORF-NAS
ORF-SJU
ORF-PUJ
ORF-SDQ
What is the cheapest time of day to fly from V1B to CB?
Find hourly flight availability from Virginia Beach 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 8, 2026.
When flying from Virginia Beach to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 8, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited Airlines from Virginia Beach to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Crew
8.6
Overall
8.0
Food
7.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Virginia Beach to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Virginia Beach 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 Beach to Caribbean by cabin class
Find flights from Virginia Beach to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Virginia Beach and Caribbean flights
Browse other Virginia Beach and Caribbean flight options. Last updated on August 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Virginia Beach to Caribbean flights
Consider these flights traveling from Virginia Beach to Caribbean.
Top 7 airlines flying from Virginia Beach to Caribbean
Discover the top 7 airlines that operate flights from Virginia Beach 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 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$379 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$509 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$177 | Average$514 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$212 | Average$587 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$516 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$237 | Average$618 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |