$101+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jul 18 — Jul 251
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 June 18, 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 June 18, 2026.
This Priceline deal was found by Cheapflights users on 6/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:30 pm
ORF
- SJU
Nonstop3h 24m
JetBlue
Fri 11/1310:00 am
SJU
- ORF
Nonstop3h 32m
JetBlue
Deal found 6/16![JetBlue logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Sun 10/46:00 am
ORF
- SJU
1 stop7h 45m
United Airlines
Tue 10/131:25 pm
SJU
- ORF
2 stops10h 19m
United Airlines
Deal found 6/15![United Airlines logo]()
$276
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
ORF
- SJU
2 stops10h 11m
American Airlines
Wed 9/96:27 am
SJU
- ORF
2 stops10h 43m
American Airlines
Deal found 6/15![American Airlines logo]()
$279
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/163:35 pm
ORF
- SJU
Nonstop3h 23m
JetBlue
Fri 8/2111:06 am
SJU
- ORF
Nonstop3h 34m
JetBlue
Deal found 6/16![JetBlue logo]()
$280
This CheapOair deal was found by Cheapflights users on 6/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/51:30 pm
ORF
- SJU
Nonstop3h 32m
Multiple Airlines
Tue 10/132:58 am
SJU
- ORF
1 stop14h 32m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/165:13 am
ORF
- SJU
1 stop11h 44m
American Airlines
Fri 8/216:00 am
SJU
- ORF
1 stop12h 50m
American Airlines
Deal found 6/18![American Airlines logo]()
$284
This JetBlue deal was found by Cheapflights users on 6/13. 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.
Mon 12/712:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Wed 12/99:00 am
SJU
- ORF
Nonstop3h 50m
JetBlue
Deal found 6/13![JetBlue logo]()
$285
This CheapOair deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Mon 9/281:30 pm
ORF
- SJU
Nonstop3h 32m
Multiple Airlines
Tue 9/296:05 am
SJU
- ORF
1 stop11h 10m
Multiple Airlines
Deal found 6/18![Multiple Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 6/13. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:00 am
ORF
- SJU
1 stop7h 40m
United Airlines
Tue 12/82:05 am
SJU
- ORF
1 stop9h 05m
United Airlines
Deal found 6/13![United Airlines logo]()
$289
This Priceline deal was found by Cheapflights users on 6/13. 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.
Sun 9/131:30 pm
ORF
- SJU
Nonstop3h 32m
Multiple Airlines
Thu 9/176:05 am
SJU
- ORF
1 stop11h 10m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/173:00 pm
ORF
- SJU
1 stop7h 00m
Delta
Tue 9/225:41 pm
SJU
- ORF
1 stop6h 52m
Delta
Deal found 6/18![Delta logo]()
$291
This United Airlines deal was found by Cheapflights users on 6/16. 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 9/56:15 am
ORF
- SJU
1 stop6h 19m
United Airlines
Thu 9/102:55 pm
SJU
- ORF
2 stops8h 48m
United Airlines
Deal found 6/16![United Airlines logo]()
$293
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 June 18, 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 June 18, 2026.
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:25 am
ORF
- NAS
1 stop5h 24m
Delta
Thu 9/173:14 pm
NAS
- ORF
1 stop4h 48m
Delta
Deal found 6/13![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 6/13. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:02 am
ORF
- NAS
1 stop7h 31m
United Airlines
Sun 9/202:35 pm
NAS
- ORF
2 stops19h 06m
United Airlines
Deal found 6/13![United Airlines logo]()
$304
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:20 pm
ORF
- NAS
1 stop13h 41m
American Airlines
Mon 7/203:02 pm
NAS
- ORF
1 stop8h 35m
American Airlines
Deal found 6/17![American Airlines logo]()
$310
This JetBlue deal was found by Cheapflights users on 6/13. 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.
Mon 9/287:25 am
ORF
- NAS
1 stop8h 35m
JetBlue
Thu 10/15:57 pm
NAS
- ORF
1 stop4h 44m
JetBlue
Deal found 6/13![JetBlue logo]()
$334
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/188:50 am
ORF
- SJU
2 stops10h 10m
Southwest
Tue 8/258:20 am
SJU
- ORF
2 stops9h 00m
Southwest
Deal found 6/17![Southwest logo]()
$348
This Priceline deal was found by Cheapflights users on 6/13. 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.
Thu 8/69:34 pm
ORF
- PUJ
2 stops22h 45m
Frontier
Mon 8/109:29 pm
PUJ
- ORF
2 stops37h 46m
Frontier
Deal found 6/13![Frontier logo]()
$553
This Delta deal was found by Cheapflights users on 6/14. 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 9/145:30 am
ORF
- NAS
1 stop8h 19m
Delta
Thu 9/171:15 pm
NAS
- ORF
1 stop6h 47m
Delta
Deal found 6/14![Delta logo]()
$300
This Breeze Airways deal was found by Cheapflights users on 6/16. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/166:00 am
ORF
- PUJ
1 stop13h 11m
Breeze Airways
Sun 7/198:11 pm
PUJ
- ORF
1 stop26h 57m
Breeze Airways
Deal found 6/16![Breeze Airways logo]()
$606
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:02 am
ORF
- NAS
1 stop7h 31m
United Airlines
Sun 9/132:35 pm
NAS
- ORF
1 stop8h 19m
United Airlines
Deal found 6/17![United Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/278:20 pm
ORF
- NAS
1 stop15h 19m
American Airlines
Sat 8/16:45 pm
NAS
- ORF
1 stop4h 52m
American Airlines
Deal found 6/15![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:02 am
ORF
- NAS
1 stop7h 31m
United Airlines
Mon 9/142:35 pm
NAS
- ORF
1 stop8h 19m
United Airlines
Deal found 6/17![United Airlines logo]()
$310
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am
ORF
- NAS
1 stop7h 48m
JetBlue
Wed 9/212:20 pm
NAS
- ORF
1 stop8h 42m
JetBlue
Deal found 6/17![JetBlue logo]()
$344
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:00 am
ORF
- SJU
1 stop8h 31m
Delta
Fri 10/25:41 pm
SJU
- ORF
1 stop6h 52m
Delta
Deal found 6/17![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 6/15. 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.
Fri 10/912:25 pm
ORF
- SJU
2 stops9h 55m
Southwest
Sat 10/315:30 am
SJU
- ORF
2 stops9h 50m
Southwest
Deal found 6/15![Southwest logo]()
$359
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:59 pm
ORF
- NAS
2 stops17h 34m
United Airlines
Sun 9/132:35 pm
NAS
- ORF
2 stops19h 55m
United Airlines
Deal found 6/17![United Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 6/17. 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.
Thu 7/236:00 am
ORF
- PUJ
1 stop13h 11m
Multiple Airlines
Sun 7/2611:50 am
PUJ
- ORF
2 stops23h 25m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$760
This American Airlines deal was found by Cheapflights users on 6/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/258:20 pm
ORF
- SXM
2 stops19h 24m
American Airlines
Thu 7/304:45 pm
SXM
- ORF
2 stops19h 49m
American Airlines
Deal found 6/13![American Airlines logo]()
$356
This JetBlue deal was found by Cheapflights users on 6/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/271:30 pm
ORF
- SJU
Nonstop3h 32m
JetBlue
Wed 9/304:30 pm
SJU
- ORF
1 stop6h 11m
JetBlue
Deal found 6/17![JetBlue logo]()
$375
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/269:00 am
ORF
- MBJ
1 stop7h 34m
Delta
Fri 10/21:25 pm
MBJ
- ORF
1 stop10h 08m
Delta
Deal found 6/15![Delta logo]()
$352
This United Airlines deal was found by Cheapflights users on 6/16. 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.
Wed 9/96:15 am
ORF
- SJU
3 stops17h 35m
United Airlines
Sat 9/121:00 am
SJU
- ORF
2 stops8h 41m
United Airlines
Deal found 6/16![United Airlines logo]()
$334
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:45 pm
ORF
- SJU
2 stops10h 00m
Southwest
Fri 8/215:30 am
SJU
- ORF
1 stop12h 25m
Southwest
Deal found 6/17![Southwest logo]()
$419
This American Airlines deal was found by Cheapflights users on 6/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:25 pm
ORF
- STT
2 stops17h 15m
American Airlines
Wed 10/2111:45 am
STT
- ORF
2 stops10h 48m
American Airlines
Deal found 6/13![American Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:15 am
ORF
- SJU
1 stop6h 39m
United Airlines
Fri 9/251:25 pm
SJU
- ORF
2 stops10h 19m
United Airlines
Deal found 6/17![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 6/14. 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.
Sun 8/305:23 am
ORF
- PUJ
1 stop9h 16m
Delta
Thu 9/32:50 pm
PUJ
- ORF
1 stop10h 13m
Delta
Deal found 6/14![Delta logo]()
$380
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/129:00 am
ORF
- SJU
2 stops11h 15m
Southwest
Tue 12/155:45 am
SJU
- ORF
2 stops8h 40m
Southwest
Deal found 6/14![Southwest logo]()
$448
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/248:20 pm
ORF
- SXM
1 stop15h 13m
American Airlines
Tue 7/282:19 pm
SXM
- ORF
1 stop9h 18m
American Airlines
Deal found 6/15![American Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 6/13. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:05 am
ORF
- SXM
1 stop6h 28m
United Airlines
Fri 7/243:50 pm
SXM
- ORF
1 stop7h 54m
United Airlines
Deal found 6/13![United Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 11/1412:15 pm
ORF
- SJU
1 stop10h 40m
Delta
Sat 11/216:35 pm
SJU
- ORF
1 stop6h 39m
Delta
Deal found 6/14![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:01 am
ORF
- SXM
1 stop8h 50m
American Airlines
Fri 7/241:34 pm
SXM
- ORF
2 stops21h 01m
American Airlines
Deal found 6/13![American Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 6/13. 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.
Mon 7/66:00 pm
ORF
- SJU
1 stop6h 20m
Southwest
Thu 7/97:00 am
SJU
- ORF
2 stops8h 05m
Southwest
Deal found 6/13![Southwest logo]()
$465
Last-minute flights from Virginia Beach to CaribbeanDiscover last-minute flight deals from Virginia Beach to Caribbean. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Caribbean. Data last updated June 18, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/214:09 pm
ORF
- SJU
Nonstop3h 23m
JetBlue
Wed 6/2411:06 am
SJU
- ORF
Nonstop3h 34m
JetBlue
Deal found 6/14![JetBlue logo]()
$310
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/286:00 am
ORF
- NAS
1 stop5h 26m
American Airlines
Wed 7/13:47 pm
NAS
- ORF
1 stop5h 35m
American Airlines
Deal found 6/17![American Airlines logo]()
$310
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:13 am
ORF
- NAS
1 stop6h 47m
American Airlines
Tue 7/71:31 pm
NAS
- ORF
1 stop10h 06m
American Airlines
Deal found 6/16![American Airlines logo]()
$316
This Priceline deal was found by Cheapflights users on 6/13. 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.
Sun 7/59:34 pm
ORF
- SJU
1 stop10h 23m
Multiple Airlines
Fri 7/1011:44 am
SJU
- ORF
Nonstop3h 34m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$316
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/79:34 pm
ORF
- SJU
1 stop28h 41m
Frontier
Tue 7/148:37 pm
SJU
- ORF
1 stop24h 02m
Frontier
Deal found 6/15![Frontier logo]()
$296
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:34 pm
ORF
- SJU
1 stop13h 09m
Frontier
Mon 7/1310:48 pm
SJU
- ORF
1 stop21h 51m
Frontier
Deal found 6/15![Frontier logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:25 am
ORF
- NAS
2 stops7h 48m
American Airlines
Tue 7/144:10 pm
NAS
- ORF
1 stop7h 27m
American Airlines
Deal found 6/15![American Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 6/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:59 pm
ORF
- NAS
1 stop13h 41m
American Airlines
Mon 7/137:39 am
NAS
- ORF
1 stop15h 58m
American Airlines
Deal found 6/14![American Airlines logo]()
$315
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/134:13 pm
ORF
- SJU
Nonstop3h 22m
Multiple Airlines
Mon 7/2010:48 pm
SJU
- ORF
1 stop21h 51m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 7/158:15 pm
ORF
- NAS
1 stop15h 13m
United Airlines
Wed 7/222:53 pm
NAS
- ORF
1 stop7h 37m
United Airlines
Deal found 6/15![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 6/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/178:20 pm
ORF
- NAS
1 stop13h 41m
American Airlines
Mon 7/203:56 pm
NAS
- ORF
1 stop5h 27m
American Airlines
Deal found 6/13![American Airlines logo]()
$306
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Mon 7/204:13 pm
ORF
- SJU
Nonstop3h 22m
JetBlue
Fri 7/2411:44 am
SJU
- ORF
Nonstop3h 34m
JetBlue
Deal found 6/18![JetBlue logo]()
$320
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 June 18, 2026.
Search for one-way flight options from Virginia Beach to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
ORF
- NAS
2 stops7h 26m
American Airlines
Deal found 6/17![American Airlines logo]()
$101
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:10 pm
ORF
- NAS
1 stop19h 23m
United Airlines
Deal found 6/17![United Airlines logo]()
$113
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1212:15 pm
ORF
- SJU
1 stop11h 33m
Delta
Deal found 6/16![Delta logo]()
$122
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am
ORF
- SJU
2 stops9h 40m
American Airlines
Deal found 6/16![American Airlines logo]()
$127
This JetBlue deal was found by Cheapflights users on 6/15. 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.
Wed 9/91:30 pm
ORF
- SJU
Nonstop3h 32m
JetBlue
Deal found 6/15![JetBlue logo]()
$128
This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:30 pm
ORF
- SJU
Nonstop3h 32m
JetBlue
Deal found 6/16![JetBlue logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/107:05 am
ORF
- SJU
1 stop6h 36m
Multiple Airlines
Deal found 6/16![Multiple Airlines logo]()
$140
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1012:05 pm
ORF
- SJU
1 stop11h 47m
Delta
Deal found 6/15![Delta logo]()
$142
This JetBlue deal was found by Cheapflights users on 6/15. 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 12/1312:50 pm
ORF
- SJU
Nonstop3h 30m
JetBlue
Deal found 6/15![JetBlue logo]()
$143
This Delta deal was found by Cheapflights users on 6/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/97:00 am
ORF
- SJU
1 stop9h 20m
Delta
Deal found 6/15![Delta logo]()
$147
This JetBlue deal was found by Cheapflights users on 6/15. 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 8/93:35 pm
ORF
- SJU
Nonstop3h 23m
JetBlue
Deal found 6/15![JetBlue logo]()
$148
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:00 am
ORF
- SJU
1 stop15h 00m
American Airlines
Deal found 6/16![American Airlines logo]()
$150
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 June 18, 2026.
Round-trip from | $275 (Priceline) |
|---|---|
One-way from | $101 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $427 |
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 June 18, 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
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Sun 9/13
8:25 am-1:49 pm
1 stop5h 24m
Nassau Intl
Thu 9/17
3:14 pm-8:02 pm
1 stop4h 48m
$300
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Mon 9/14
5:30 am-1:49 pm
1 stop8h 19m
Nassau Intl
Thu 9/17
1:15 pm-8:02 pm
1 stop6h 47m
$300
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Thu 9/17
6:02 am-1:33 pm
1 stop7h 31m
Nassau Intl
Sun 9/20
2:35 pm-9:41 am
2 stops19h 06m
$304
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Fri 7/17
8:20 pm-10:01 am
1 stop13h 41m
Nassau Intl
Mon 7/20
3:02 pm-11:37 pm
1 stop8h 35m
$310
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Fri 9/11
6:02 am-1:33 pm
1 stop7h 31m
Nassau Intl
Sun 9/13
2:35 pm-10:54 pm
1 stop8h 19m
$310
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Fri 9/11
6:02 am-1:33 pm
1 stop7h 31m
Nassau Intl
Mon 9/14
2:35 pm-10:54 pm
1 stop8h 19m
$310
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Thu 9/10
7:59 pm-1:33 pm
2 stops17h 34m
Nassau Intl
Sun 9/13
2:35 pm-10:30 am
2 stops19h 55m
$314
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Mon 7/27
8:20 pm-11:39 am
1 stop15h 19m
Nassau Intl
Sat 8/1
6:45 pm-11:37 pm
1 stop4h 52m
$316
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Sun 9/27
8:00 am-4:31 pm
1 stop8h 31m
San Juan Luis Munoz Marin Intl
Fri 10/2
5:41 pm-12:33 am
1 stop6h 52m
$316
NorfolkNassau
ORF - NAS
ORFNAS
Norfolk
Mon 9/28
7:25 am-4:00 pm
1 stop8h 35m
Nassau Intl
Thu 10/1
5:57 pm-10:41 pm
1 stop4h 44m
$334
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-SJU
ORF-NAS
ORF-SXM
ORF-PUJ
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-SJU
ORF-NAS
ORF-SXM
ORF-PUJ
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 June 18, 2026.
When flying from Virginia Beach to Caribbean, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 30% versus a flight in the morning.
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 June 18, 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.
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Food
7.0
Boarding
8.1
Overall
7.9
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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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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 June 18, 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$96 | Average$329 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$107 | Average$500 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$503 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$205 | Average$594 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$212 | Average$586 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$515 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |