$89+ 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 4/18. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Apr 18 — Apr 251
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
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 Beach to Caribbean
Cheapest
Best
Last-minute
One-way
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 March 19, 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 March 19, 2026.
This American Airlines deal was found by Cheapflights users on 3/18. 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.
Tue 4/146:15 am
ORF
- SJU
1 stop8h 37m
American Airlines
Thu 4/166:00 am
SJU
- ORF
1 stop6h 55m
American Airlines
Deal found 3/18![American Airlines logo]()
$186
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/265:50 am
ORF
- SJU
1 stop10h 33m
Delta
Thu 4/301:25 pm
SJU
- ORF
1 stop9h 39m
Delta
Deal found 3/19![Delta logo]()
$206
This Priceline deal was found by Cheapflights users on 3/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:02 pm
ORF
- SJU
1 stop7h 59m
Frontier
Fri 5/86:09 pm
SJU
- ORF
1 stop24h 20m
Frontier
Deal found 3/17![Frontier logo]()
$212
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Tue 4/146:11 am
ORF
- SJU
1 stop6h 23m
United Airlines
Wed 4/227:20 am
SJU
- ORF
1 stop6h 51m
United Airlines
Deal found 3/15![United Airlines logo]()
$218
This United Airlines deal was found by Cheapflights users on 3/16. 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 4/116:11 am
ORF
- SJU
2 stops14h 23m
United Airlines
Wed 4/151:00 am
SJU
- ORF
2 stops8h 31m
United Airlines
Deal found 3/16![United Airlines logo]()
$223
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:25 am
ORF
- SJU
1 stop6h 55m
Southwest
Wed 4/225:05 am
SJU
- ORF
1 stop12h 45m
Southwest
Deal found 3/15![Southwest logo]()
$228
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 pm
ORF
- SJU
1 stop8h 01m
Frontier
Wed 5/63:33 pm
SJU
- ORF
1 stop28h 44m
Frontier
Deal found 3/17![Frontier logo]()
$231
This American Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 4/117:58 pm
ORF
- SJU
1 stop14h 50m
American Airlines
Fri 4/1710:03 am
SJU
- ORF
1 stop13h 56m
American Airlines
Deal found 3/16![American Airlines logo]()
$232
This United Airlines deal was found by Cheapflights users on 3/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:04 am
ORF
- SJU
2 stops14h 30m
United Airlines
Thu 4/234:55 pm
SJU
- ORF
1 stop6h 45m
United Airlines
Deal found 3/18![United Airlines logo]()
$241
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/261:36 pm
ORF
- SJU
Nonstop3h 59m
Multiple Airlines
Thu 4/3012:57 pm
SJU
- ORF
1 stop7h 05m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$245
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/318:41 pm
ORF
- SJU
1 stop15h 08m
Multiple Airlines
Tue 4/76:30 am
SJU
- ORF
1 stop8h 05m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$246
This CheapOair deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/318:41 pm
ORF
- STT
1 stop18h 47m
Spirit Airlines
Mon 4/64:35 pm
STT
- ORF
1 stop27h 11m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$305
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 March 19, 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 March 19, 2026.
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 4/276:11 am
ORF
- SJU
1 stop6h 23m
United Airlines
Thu 4/301:00 am
SJU
- ORF
2 stops8h 31m
United Airlines
Deal found 3/15![United Airlines logo]()
$308
This American Airlines deal was found by Cheapflights users on 3/14. 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 4/247:52 pm
ORF
- SXM
1 stop17h 28m
American Airlines
Fri 5/84:35 pm
SXM
- ORF
2 stops16h 00m
American Airlines
Deal found 3/14![American Airlines logo]()
$326
This CheapOair deal was found by Cheapflights users on 3/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:59 pm
ORF
- STT
2 stops17h 31m
Spirit Airlines
Sat 5/95:10 pm
STT
- ORF
1 stop23h 36m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$383
This Delta deal was found by Cheapflights users on 3/17. 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.
Wed 4/297:07 am
ORF
- SDQ
1 stop11h 27m
Delta
Mon 5/42:37 pm
SDQ
- ORF
1 stop7h 56m
Delta
Deal found 3/17![Delta logo]()
$425
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/91:15 pm
ORF
- SJU
2 stops10h 25m
Southwest
Sat 5/166:25 am
SJU
- ORF
2 stops11h 45m
Southwest
Deal found 3/19![Southwest logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1412:06 pm
ORF
- PUJ
2 stops27h 21m
Frontier
Mon 5/183:35 pm
PUJ
- ORF
1 stop19h 36m
Frontier
Deal found 3/15![Frontier logo]()
$527
This Priceline deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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.
Fri 5/111:27 am
ORF
- PUJ
1 stop26h 27m
Multiple Airlines
Mon 5/46:42 pm
PUJ
- ORF
1 stop15h 50m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$582
This American Airlines deal was found by Cheapflights users on 3/16. 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 4/177:58 pm
ORF
- SXM
2 stops17h 22m
American Airlines
Tue 4/212:21 pm
SXM
- ORF
2 stops19h 51m
American Airlines
Deal found 3/16![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 3/18. 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.
Wed 5/136:15 am
ORF
- SXM
1 stop9h 07m
American Airlines
Fri 5/291:40 pm
SXM
- ORF
2 stops18h 43m
American Airlines
Deal found 3/18![American Airlines logo]()
$331
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 6/86:05 am
ORF
- MBJ
1 stop10h 05m
United Airlines
Mon 6/224:12 pm
MBJ
- ORF
1 stop6h 32m
United Airlines
Deal found 3/15![United Airlines logo]()
$372
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 5/96:00 am
ORF
- AUA
1 stop9h 20m
United Airlines
Sat 5/163:10 pm
AUA
- ORF
2 stops18h 21m
United Airlines
Deal found 3/19![United Airlines logo]()
$396
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Tue 5/127:24 pm
ORF
- PUJ
2 stops15h 27m
American Airlines
Fri 5/155:25 pm
PUJ
- ORF
2 stops15h 10m
American Airlines
Deal found 3/14![American Airlines logo]()
$365
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:35 am
ORF
- NAS
1 stop6h 55m
Southwest
Wed 6/32:10 pm
NAS
- ORF
2 stops7h 45m
Southwest
Deal found 3/16![Southwest logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:41 pm
ORF
- SDQ
1 stop16h 34m
Spirit Airlines
Wed 4/152:35 pm
SDQ
- ORF
1 stop29h 27m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$443
This FlightHub deal was found by Cheapflights users on 3/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3010:50 am
ORF
- UVF
2 stops28h 29m
JetBlue
Fri 6/54:41 pm
UVF
- ORF
2 stops42h 32m
JetBlue
Deal found 3/15![JetBlue logo]()
$900
This Southwest deal was found by Cheapflights users on 3/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:40 am
ORF
- NAS
2 stops9h 50m
Southwest
Fri 4/242:10 pm
NAS
- ORF
2 stops8h 45m
Southwest
Deal found 3/18![Southwest logo]()
$442
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
ORF
- PUJ
1 stop9h 12m
United Airlines
Sat 5/94:40 pm
PUJ
- ORF
1 stop7h 10m
United Airlines
Deal found 3/19![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 3/16. 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.
Wed 4/297:07 am
ORF
- SDQ
1 stop11h 27m
Delta
Sun 5/32:37 pm
SDQ
- ORF
1 stop10h 00m
Delta
Deal found 3/16![Delta logo]()
$502
This Delta deal was found by Cheapflights users on 3/17. 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.
Fri 5/155:20 am
ORF
- SDQ
1 stop8h 04m
Delta
Mon 5/182:49 pm
SDQ
- ORF
1 stop9h 59m
Delta
Deal found 3/17![Delta logo]()
$502
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Mon 4/206:11 am
ORF
- AUA
2 stops10h 29m
United Airlines
Sat 4/253:10 pm
AUA
- ORF
2 stops18h 21m
United Airlines
Deal found 3/17![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Thu 6/115:30 am
ORF
- AUA
1 stop11h 29m
American Airlines
Mon 6/154:50 pm
AUA
- ORF
2 stops19h 44m
American Airlines
Deal found 3/17![American Airlines logo]()
$416
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/63:10 pm
ORF
- SJU
2 stops9h 35m
Southwest
Tue 6/97:00 am
SJU
- ORF
2 stops8h 50m
Southwest
Deal found 3/16![Southwest logo]()
$462
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Tue 5/56:05 am
ORF
- AUA
1 stop9h 15m
United Airlines
Sat 5/93:10 pm
AUA
- ORF
2 stops19h 45m
United Airlines
Deal found 3/16![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Mon 4/275:30 pm
ORF
- STT
2 stops18h 05m
American Airlines
Sat 5/95:05 pm
STT
- ORF
2 stops17h 16m
American Airlines
Deal found 3/14![American Airlines logo]()
$420
This CheapOair deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:06 pm
ORF
- PUJ
1 stop26h 18m
Frontier
Mon 6/83:35 pm
PUJ
- ORF
2 stops19h 46m
Frontier
Deal found 3/16![Frontier logo]()
$618
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:11 am
ORF
- SJU
2 stops14h 23m
United Airlines
Thu 4/231:00 am
SJU
- ORF
2 stops8h 31m
United Airlines
Deal found 3/14![United Airlines logo]()
$420
This CheapOair deal was found by Cheapflights users on 3/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:41 pm
ORF
- PUJ
1 stop19h 15m
Spirit Airlines
Fri 4/35:01 pm
PUJ
- ORF
2 stops28h 46m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$617
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Wed 4/298:14 pm
ORF
- SDQ
2 stops18h 45m
American Airlines
Tue 5/56:00 am
SDQ
- ORF
1 stop13h 22m
American Airlines
Deal found 3/17![American Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:10 pm
ORF
- SJU
2 stops9h 35m
Southwest
Sat 6/205:00 am
SJU
- ORF
1 stop12h 05m
Southwest
Deal found 3/16![Southwest logo]()
$532
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:11 am
ORF
- SJU
2 stops14h 23m
United Airlines
Thu 4/234:55 pm
SJU
- ORF
1 stop6h 45m
United Airlines
Deal found 3/14![United Airlines logo]()
$422
Last-minute flights from Virginia Beach to CaribbeanDiscover last-minute flight deals from Virginia Beach to Caribbean. Data last updated March 19, 2026 and is based on user searches.
Discover last-minute flight deals from Virginia Beach to Caribbean. Data last updated March 19, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/266:43 pm
ORF
- SJU
1 stop7h 15m
Frontier
Sun 3/2911:07 am
SJU
- ORF
1 stop6h 41m
Frontier
Deal found 3/16![Frontier logo]()
$250
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/318:41 pm
ORF
- SJU
1 stop15h 08m
Multiple Airlines
Tue 4/76:30 am
SJU
- ORF
1 stop8h 05m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$246
This United Airlines deal was found by Cheapflights users on 3/16. 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 4/116:11 am
ORF
- SJU
2 stops14h 23m
United Airlines
Wed 4/151:00 am
SJU
- ORF
2 stops8h 31m
United Airlines
Deal found 3/16![United Airlines logo]()
$223
This American Airlines deal was found by Cheapflights users on 3/16. 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.
Sat 4/117:52 pm
ORF
- SJU
1 stop13h 21m
American Airlines
Thu 4/1610:03 am
SJU
- ORF
1 stop9h 19m
American Airlines
Deal found 3/16![American Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/118:41 pm
ORF
- SJU
1 stop15h 08m
Multiple Airlines
Wed 4/1511:30 am
SJU
- ORF
2 stops23h 02m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$258
This American Airlines deal was found by Cheapflights users on 3/18. 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.
Tue 4/146:15 am
ORF
- SJU
1 stop8h 37m
American Airlines
Thu 4/166:00 am
SJU
- ORF
1 stop6h 55m
American Airlines
Deal found 3/18![American Airlines logo]()
$186
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Tue 4/146:11 am
ORF
- SJU
1 stop6h 23m
United Airlines
Wed 4/227:20 am
SJU
- ORF
1 stop6h 51m
United Airlines
Deal found 3/15![United Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:25 am
ORF
- SJU
1 stop6h 55m
Southwest
Wed 4/225:05 am
SJU
- ORF
1 stop12h 45m
Southwest
Deal found 3/15![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 3/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
ORF
- SJU
1 stop8h 44m
United Airlines
Thu 4/234:55 pm
SJU
- ORF
1 stop6h 45m
United Airlines
Deal found 3/18![United Airlines logo]()
$241
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:02 pm
ORF
- SJU
1 stop7h 59m
Multiple Airlines
Fri 4/2412:57 pm
SJU
- ORF
1 stop7h 05m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” 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 4/265:50 am
ORF
- SJU
1 stop10h 33m
Delta
Thu 4/301:25 pm
SJU
- ORF
1 stop9h 39m
Delta
Deal found 3/19![Delta logo]()
$206
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/261:36 pm
ORF
- SJU
Nonstop3h 59m
Multiple Airlines
Thu 4/3012:57 pm
SJU
- ORF
1 stop7h 05m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$245
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 March 19, 2026.
Search for one-way flight options from Virginia Beach to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 19, 2026.
This Southwest deal was found by Cheapflights users on 3/17. 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 4/1411:10 am
ORF
- SJU
1 stop11h 30m
Southwest
Deal found 3/17![Southwest logo]()
$89
This American Airlines deal was found by Cheapflights users on 3/17. 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 4/266:15 am
ORF
- SJU
1 stop15h 09m
American Airlines
Deal found 3/17![American Airlines logo]()
$93
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Mon 4/137:15 pm
ORF
- SJU
1 stop9h 17m
American Airlines
Deal found 3/17![American Airlines logo]()
$95
This American Airlines deal was found by Cheapflights users on 3/16. 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 3/307:41 pm
ORF
- SJU
1 stop13h 19m
American Airlines
Deal found 3/16![American Airlines logo]()
$103
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:12 pm
ORF
- SJU
1 stop10h 52m
Frontier
Deal found 3/17![Frontier logo]()
$106
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Sat 4/116:11 am
ORF
- SJU
2 stops14h 23m
United Airlines
Deal found 3/17![United Airlines logo]()
$109
This Priceline deal was found by Cheapflights users on 3/18. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:12 pm
ORF
- SJU
1 stop28h 36m
Frontier
Deal found 3/18![Frontier logo]()
$112
This CheapOair deal was found by Cheapflights users on 3/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:41 pm
ORF
- SJU
1 stop15h 08m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 3/18. 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 4/68:41 pm
ORF
- SJU
1 stop15h 08m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/1412:25 pm
ORF
- SJU
1 stop11h 34m
Delta
Deal found 3/18![Delta logo]()
$123
This eDestinos deal was found by Cheapflights users on 3/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:27 am
ORF
- SJU
2 stops38h 34m
Frontier
Deal found 3/18![Frontier logo]()
$125
This Frontier deal was found by Cheapflights users on 3/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:24 pm
ORF
- SJU
1 stop6h 44m
Frontier
Deal found 3/17![Frontier logo]()
$127
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 March 19, 2026.
Round-trip from | $186 (American Airlines) |
|---|---|
One-way from | $89 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $401 |
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 March 19, 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
NorfolkSan Juan
ORF - SJU
ORFSJU
Norfolk
Mon 4/27
6:11 am-12:34 pm
1 stop6h 23m
San Juan Luis Munoz Marin Intl
Thu 4/30
1:00 am-9:31 am
2 stops8h 31m
$308
NorfolkSimpson Bay
ORF - SXM
ORFSXM
Norfolk
Fri 4/24
7:52 pm-1:20 pm
1 stop17h 28m
Simpson Bay Princess Juliana
Fri 5/8
4:35 pm-8:35 am
2 stops16h 00m
$326
NorfolkSimpson Bay
ORF - SXM
ORFSXM
Norfolk
Fri 4/17
7:58 pm-1:20 pm
2 stops17h 22m
Simpson Bay Princess Juliana
Tue 4/21
2:21 pm-10:12 am
2 stops19h 51m
$326
NorfolkSimpson Bay
ORF - SXM
ORFSXM
Norfolk
Wed 5/13
6:15 am-3:22 pm
1 stop9h 07m
Simpson Bay Princess Juliana
Fri 5/29
1:40 pm-8:23 am
2 stops18h 43m
$331
NorfolkPunta Cana
ORF - PUJ
ORFPUJ
Norfolk
Tue 5/12
7:24 pm-10:51 am
2 stops15h 27m
Punta Cana
Fri 5/15
5:25 pm-8:35 am
2 stops15h 10m
$365
NorfolkMontego Bay
ORF - MBJ
ORFMBJ
Norfolk
Mon 6/8
6:05 am-3:10 pm
1 stop10h 05m
Montego Bay Sangster Intl
Mon 6/22
4:12 pm-11:44 pm
1 stop6h 32m
$372
NorfolkSaint Thomas Island
ORF - STT
ORFSTT
Norfolk
Mon 4/27
5:59 pm-11:30 am
2 stops17h 31m
Saint Thomas Island Cyril E King
Sat 5/9
5:10 pm-4:46 pm
1 stop23h 36m
$383
NorfolkOranjestad
ORF - AUA
ORFAUA
Norfolk
Sat 5/9
6:00 am-3:20 pm
1 stop9h 20m
Oranjestad Reina Beatrix
Sat 5/16
3:10 pm-9:31 am
2 stops18h 21m
$396
NorfolkPunta Cana
ORF - PUJ
ORFPUJ
Norfolk
Mon 5/4
6:00 am-3:12 pm
1 stop9h 12m
Punta Cana
Sat 5/9
4:40 pm-11:50 pm
1 stop7h 10m
$402
NorfolkOranjestad
ORF - AUA
ORFAUA
Norfolk
Mon 4/20
6:11 am-4:40 pm
2 stops10h 29m
Oranjestad Reina Beatrix
Sat 4/25
3:10 pm-9:31 am
2 stops18h 21m
$416
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-SXM
ORF-STT
ORF-SDQ
ORF-PUJ
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-SXM
ORF-STT
ORF-SDQ
What is the cheapest month to book a flight from Virginia Beach to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Virginia Beach to Caribbean (average of $129). Flying from Virginia Beach to Caribbean in March is currently the most expensive (average of $220). 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 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 March 19, 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 68% 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 March 19, 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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
Top countries
Top destinations
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 March 19, 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 8 airlines flying from Virginia Beach to Caribbean
Discover the top 8 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 March 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$94 | Average$417 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$96 | Average$292 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$128 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$159 | Average$534 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$205 | Average$623 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$212 | Average$554 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$561 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$646 | Average$646 | FlexibilityNo cancel fee | On-time75% |