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Caribbean

$113+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap 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 septiembre 11, 2025.

Round-trip from

$225
(Delta)

One-way from

$113
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$323
From Virginia Beach to Caribbean
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One-way flight from Virginia Beach to Caribbean
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Highest demand for flights based on searches. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Virginia Beach to Caribbean

Cheapest flights from Virginia Beach to Caribbean
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 septiembre 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/103:10 pmORF - SJU
1 stop7h 03mDelta
jue. 11/136:36 pmSJU - ORF
1 stop6h 39mDelta
Deal found 9/11$225
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/259:54 amORF - SJU
1 stop13h 11mAmerican Airlines
mié. 10/292:35 pmSJU - ORF
2 stops8h 25mAmerican Airlines
Deal found 9/11$230
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/229:54 amORF - SJU
1 stop14h 05mAmerican Airlines
jue. 10/235:30 amSJU - ORF
1 stop6h 35mAmerican Airlines
Deal found 9/10$240
This Frontier deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/25:12 pmORF - SJU
1 stop9h 22mFrontier
lun. 10/69:26 pmSJU - ORF
2 stops19h 23mFrontier
Deal found 9/11$244
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/268:30 amORF - SJU
1 stop15h 29mAmerican Airlines
sáb. 11/15:30 amSJU - ORF
1 stop6h 35mAmerican Airlines
Deal found 9/10$245
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/56:00 amORF - SJU
1 stop7h 45mUnited Airlines
vie. 10/171:05 amSJU - ORF
2 stops13h 35mUnited Airlines
Deal found 9/10$248
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/96:00 amORF - SJU
2 stops14h 00mUnited Airlines
lun. 12/152:05 amSJU - ORF
2 stops13h 29mUnited Airlines
Deal found 9/10$250
This Priceline deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/25:12 pmORF - SJU
1 stop9h 22mFrontier
sáb. 10/43:39 amSJU - ORF
1 stop13h 18mFrontier
Deal found 9/10$253
This United Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/146:00 amORF - SJU
1 stop7h 45mUnited Airlines
jue. 10/161:05 amSJU - ORF
2 stops8h 32mUnited Airlines
Deal found 9/11$258
This Cheapflightsfares deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/78:01 amORF - STT
1 stop6h 10mSpirit Airlines
lun. 11/104:06 pmSTT - ORF
1 stop9h 01mSpirit Airlines
Deal found 9/11$261
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/68:32 pmORF - SJU
1 stop12h 20mSpirit Airlines
lun. 12/86:00 amSJU - ORF
1 stop9h 12mSpirit Airlines
Deal found 9/10$262
This Cheapflightsfares deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/116:00 amORF - STT
1 stop5h 28mSpirit Airlines
mar. 11/181:33 pmSTT - ORF
1 stop11h 07mSpirit Airlines
Deal found 9/10$263

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 septiembre 11, 2025.
Use the filters below to find and compare flights from Virginia Beach to Caribbean that are best for you.

Fly from

Virginia Beach

Fly to

Caribbean

Route

Depart

Return

Price

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

vie. 10/3

1:10 pm-12:45 am

1 stop11h 35m

San Juan Luis Munoz Marin Intl

dom. 10/5

5:45 am-4:50 pm

1 stop11h 05m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

sáb. 10/18

8:30 am-11:05 pm

1 stop14h 35m

San Juan Luis Munoz Marin Intl

vie. 10/24

5:00 pm-11:16 pm

1 stop6h 16m

$225

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

lun. 11/10

6:35 am-3:40 pm

1 stop8h 05m

San Juan Luis Munoz Marin Intl

mar. 11/11

2:05 am-2:34 pm

2 stops13h 29m

$225

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

mar. 11/11

6:00 am-12:28 pm

1 stop5h 28m

Saint Thomas Island Cyril E King

mar. 11/18

1:33 pm-11:40 pm

1 stop11h 07m

$263

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jue. 10/2

6:45 pm-12:45 am

1 stop6h 00m

San Juan Luis Munoz Marin Intl

lun. 10/6

5:30 pm-11:25 pm

1 stop5h 55m

$285

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

mié. 11/19

6:00 am-4:50 pm

1 stop9h 50m

Oranjestad Reina Beatrix

lun. 11/24

5:55 pm-12:15 am

1 stop7h 20m

$286

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

vie. 11/14

7:29 pm-2:42 pm

2 stops18h 13m

Oranjestad Reina Beatrix

vie. 11/21

5:45 pm-9:36 am

2 stops16h 51m

$291

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

mar. 10/28

6:14 am-12:30 pm

1 stop6h 16m

Oranjestad Reina Beatrix

sáb. 11/1

2:45 pm-10:20 am

2 stops19h 35m

$291

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

jue. 1/8

5:30 am-1:00 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

vie. 1/16

7:30 am-4:59 pm

1 stop10h 29m

$295

NorfolkOranjestad

ORF - AUA

ORFAUA

Norfolk

vie. 1/16

7:40 pm-12:30 pm

1 stop15h 50m

Oranjestad Reina Beatrix

vie. 1/30

3:10 pm-10:55 pm

1 stop8h 45m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 results
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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.
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

What is the cheapest month to book a flight from Virginia Beach to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Virginia Beach to Caribbean (average of $254). Flying from Virginia Beach to Caribbean in June is currently the most expensive (average of $339). 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 septiembre 11, 2025.

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 septiembre 11, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Virginia Beach to Caribbean?

    A quick flight from Virginia Beach to Caribbean can take about 8h 05m. Southwest provides one of the quickest options available for as low as $225. The distance from Virginia Beach to Caribbean is about 1416 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Virginia Beach to Caribbean one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $113. Users have also found prices from $113 and $143 on American Airlines and Spirit Airlines, respectively.

  • What are the most popular routes from Virginia Beach to Caribbean?

    Most travelers choose Norfolk - San Juan Luis Munoz Marin Intl, Norfolk - Punta Cana or Norfolk - Montego Bay Sangster Intl when deciding on the best route from Virginia Beach to Caribbean.

  • Can I find deals for flights from Virginia Beach to Caribbean that include hotel bookings?

    Yes. In addition to deals on Virginia Beach to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia Beach to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia Beach to Caribbean.

  • Can I find deals for business class flights from Virginia Beach to Caribbean?

    Yes. Cheapflights offers flight deals from Virginia Beach to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Virginia Beach to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Virginia Beach to Caribbean (average of $254). Flying from Virginia Beach to Caribbean in June is currently the most expensive (average of $339). 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.

See more FAQs

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See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$284FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$428FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$563FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$593FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$524FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$611FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$257Average$643FlexibilityNo cancel feeOn-time63%

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