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$123+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
abr. 22 — abr. 291
mar. 4/22
mar. 4/29
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 abril 17, 2025.

Round-trip from

$245
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$459
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. 11% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 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 abril 17, 2025.

This American Airlines deal was found by Cheapflights users on 4/17. 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.
mar. 9/166:50 amORF - SJU
1 stop13h 20mAmerican Airlines
mar. 9/305:25 pmSJU - ORF
1 stop6h 04mAmerican Airlines
Deal found 4/17$245
This Cheapflightsfares deal was found by Cheapflights users on 4/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/1012:13 pmORF - SJU
1 stop12h 41mSpirit Airlines
vie. 5/161:59 amSJU - ORF
1 stop8h 30mSpirit Airlines
Deal found 4/17$253
This Delta deal was found by Cheapflights users on 4/16. 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.
mar. 9/167:00 amORF - SJU
1 stop9h 18mDelta
mar. 9/231:13 pmSJU - ORF
1 stop9h 42mDelta
Deal found 4/16$255
This Mytrip deal was found by Cheapflights users on 4/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/1612:13 pmORF - STT
1 stop25h 23mSpirit Airlines
vie. 5/232:41 pmSTT - ORF
1 stop19h 48mSpirit Airlines
Deal found 4/16$264
This CheapOair deal was found by Cheapflights users on 4/17. 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.
sáb. 5/1012:13 pmORF - SJU
1 stop12h 41mMultiple Airlines
sáb. 5/179:30 pmSJU - ORF
1 stop13h 01mMultiple Airlines
Deal found 4/17$275
This Southwest deal was found by Cheapflights users on 4/15. 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.
mar. 5/135:10 pmORF - SJU
1 stop6h 45mSouthwest
sáb. 5/174:35 pmSJU - ORF
1 stop6h 20mSouthwest
Deal found 4/15$285
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/258:32 pmORF - SJU
1 stop6h 17mFrontier
mié. 4/303:56 amSJU - ORF
1 stop6h 35mFrontier
Deal found 4/16$297
This United Airlines deal was found by Cheapflights users on 4/16. 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.
lun. 11/176:00 amORF - SJU
1 stop6h 17mUnited Airlines
jue. 11/202:05 amSJU - ORF
1 stop7h 50mUnited Airlines
Deal found 4/16$304
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/3112:13 pmORF - MBJ
2 stops23h 49mMultiple Airlines
mié. 6/412:07 pmMBJ - ORF
1 stop21h 38mMultiple Airlines
Deal found 4/17$343
This Priceline deal was found by Cheapflights users on 4/16. 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.
sáb. 4/268:37 pmORF - PUJ
1 stop15h 07mSpirit Airlines
vie. 5/212:39 pmPUJ - ORF
1 stop7h 01mSpirit Airlines
Deal found 4/16$368
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
lun. 5/1912:13 pmORF - MBJ
2 stops23h 49mSpirit Airlines
mié. 5/2812:07 pmMBJ - ORF
1 stop25h 09mSpirit Airlines
Deal found 4/16$372
This American Airlines deal was found by Cheapflights users on 4/16. 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.
mar. 7/228:18 pmORF - STX
2 stops18h 47mAmerican Airlines
sáb. 7/265:14 pmSTX - ORF
2 stops15h 59mAmerican Airlines
Deal found 4/16$384

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 abril 17, 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

mar. 9/16

6:50 am-8:10 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

mar. 9/30

5:25 pm-11:29 pm

1 stop6h 04m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

sáb. 5/10

12:13 pm-12:54 am

1 stop12h 41m

San Juan Luis Munoz Marin Intl

vie. 5/16

1:59 am-10:29 am

1 stop8h 30m

$253

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 9/16

7:00 am-4:18 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

mar. 9/23

7:00 am-4:48 pm

1 stop9h 48m

$255

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

vie. 5/16

12:13 pm-1:36 pm

1 stop25h 23m

Saint Thomas Island Cyril E King

vie. 5/23

2:41 pm-10:29 am

1 stop19h 48m

$264

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

sáb. 5/10

12:13 pm-12:54 am

1 stop12h 41m

San Juan Luis Munoz Marin Intl

sáb. 5/17

9:30 pm-10:31 am

1 stop13h 01m

$275

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom. 4/27

11:22 am-12:08 am

1 stop12h 46m

San Juan Luis Munoz Marin Intl

mié. 4/30

9:30 pm-10:31 am

1 stop13h 01m

$308

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

dom. 5/11

2:25 pm-10:30 pm

1 stop8h 05m

San Juan Luis Munoz Marin Intl

jue. 5/15

7:40 am-6:45 pm

2 stops11h 05m

$325

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

mar. 9/16

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

lun. 9/29

1:05 am-9:22 am

2 stops8h 17m

$335

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

sáb. 5/31

12:13 pm-11:02 am

2 stops23h 49m

Montego Bay Sangster Intl

mié. 6/4

12:07 pm-10:45 am

1 stop21h 38m

$343

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

sáb. 4/26

8:37 pm-11:44 am

1 stop15h 07m

Punta Cana

vie. 5/2

12:39 pm-7:40 pm

1 stop7h 01m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 51 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 December is currently the most expensive (average of $336). 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 abril 17, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 abril 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
LATAM Airlines
7.5
Good
1,761 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $126. Users have also found prices from $146 and $149 on Spirit Airlines and Frontier, respectively.

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

    Most travelers choose Norfolk - Montego Bay Sangster Intl, Norfolk - San Juan Luis Munoz Marin Intl or Norfolk - Punta Cana 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 December is currently the most expensive (average of $336). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Virginia Beach to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 abril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$422FlexibilityNo cancel feeOn-time65%
FrontierCheapest$131Average$234FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$613FlexibilityNo cancel feeOn-time69%
DeltaCheapest$233Average$520FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$256Average$579FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$256Average$623FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$349Average$610FlexibilityNo cancel feeOn-time63%

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