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$59+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$235
(FlightHub)

One-way from

$59
(Cheapflightsfares)

Popular in

December

Cheapest in

May

Average price

$387
From Virginia Beach to Caribbean
Search Deals
One-way flight from Virginia Beach to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/188:59 pmORF - STT
1 stop11h 54mSpirit Airlines
Tue 4/221:48 pmSTT - ORF
1 stop6h 16mSpirit Airlines
Deal found 2/20$208
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/268:59 pmORF - SJU
2 stops21h 45mSpirit Airlines
Sun 5/410:19 pmSJU - ORF
1 stop13h 03mSpirit Airlines
Deal found 2/19$235
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/17:16 pmORF - SJU
1 stop6h 38mFrontier
Wed 3/59:30 pmSJU - ORF
1 stop20h 28mFrontier
Deal found 2/19$238
This Delta deal was found by Cheapflights users on 2/19. 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.
Tue 4/296:55 amORF - SJU
1 stop9h 06mDelta
Thu 5/85:35 pmSJU - ORF
1 stop6h 26mDelta
Deal found 2/19$245
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/258:32 pmORF - SJU
1 stop6h 17mMultiple Airlines
Sun 4/273:52 amSJU - ORF
1 stop7h 30mMultiple Airlines
Deal found 2/19$246
This United Airlines deal was found by Cheapflights users on 2/20. 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 10/156:00 amORF - SJU
1 stop7h 45mUnited Airlines
Wed 10/221:05 amSJU - ORF
2 stops8h 30mUnited Airlines
Deal found 2/20$267
This Booking.com deal was found by Cheapflights users on 2/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/26:12 pmORF - PUJ
2 stops18h 02mFrontier
Fri 3/73:14 pmPUJ - ORF
1 stop20h 23mFrontier
Deal found 2/20$294
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/34:54 pmORF - PUJ
2 stops47h 18mMultiple Airlines
Mon 4/72:49 pmPUJ - ORF
1 stop23h 42mMultiple Airlines
Deal found 2/19$312
This Priceline deal was found by Cheapflights users on 2/19. 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.
Thu 3/205:58 pmORF - SDQ
2 stops18h 29mFrontier
Mon 3/2412:04 pmSDQ - ORF
2 stops26h 23mFrontier
Deal found 2/19$318
This FlightHub deal was found by Cheapflights users on 2/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/64:54 pmORF - MBJ
2 stops19h 08mSpirit Airlines
Wed 4/912:00 pmMBJ - ORF
2 stops22h 22mSpirit Airlines
Deal found 2/19$328
This CheapOair deal was found by Cheapflights users on 2/20. 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 3/2012:42 pmORF - PUJ
1 stop23h 35mSpirit Airlines
Tue 3/253:47 pmPUJ - ORF
2 stops26h 59mSpirit Airlines
Deal found 2/20$343
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/45:50 amORF - SJU
2 stops10h 30mAmerican Airlines
Tue 10/1412:00 pmSJU - ORF
2 stops10h 09mAmerican Airlines
Deal found 2/19$375

Find flights from Virginia Beach to Caribbean within your budget

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 February 20, 2025.

Fly from

Virginia Beach

Fly to

Caribbean

Route

Depart

Return

Price

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Fri 4/18

8:59 pm-8:53 am

1 stop11h 54m

Saint Thomas Island Cyril E King

Tue 4/22

1:48 pm-8:04 pm

1 stop6h 16m

$208

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 4/26

8:59 pm-6:44 pm

2 stops21h 45m

San Juan Luis Munoz Marin Intl

Thu 5/1

3:52 am-11:22 am

1 stop7h 30m

$235

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 3/1

7:16 pm-2:54 am

1 stop6h 38m

San Juan Luis Munoz Marin Intl

Wed 3/5

9:30 pm-4:58 pm

1 stop20h 28m

$238

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 4/29

5:30 am-11:40 am

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Thu 5/1

7:15 am-6:02 pm

1 stop10h 47m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 4/25

8:32 pm-2:49 am

1 stop6h 17m

San Juan Luis Munoz Marin Intl

Sun 4/27

3:52 am-11:22 am

1 stop7h 30m

$246

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Sun 3/2

6:12 pm-1:14 pm

2 stops18h 02m

Punta Cana

Fri 3/7

3:14 pm-10:37 am

1 stop20h 23m

$294

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Thu 4/3

4:54 pm-4:12 pm

2 stops47h 18m

Punta Cana

Mon 4/7

2:49 pm-2:31 pm

1 stop23h 42m

$312

NorfolkSanto Domingo

ORF - SDQ

ORFSDQ

Norfolk

Thu 3/20

5:58 pm-12:27 pm

2 stops18h 29m

Santo Domingo Las Americas

Mon 3/24

12:04 pm-2:27 pm

2 stops26h 23m

$318

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 4/6

4:54 pm-11:02 am

2 stops19h 08m

Montego Bay Sangster Intl

Wed 4/9

12:00 pm-11:22 am

2 stops22h 22m

$328

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 3/25

6:10 am-3:36 pm

1 stop9h 26m

San Juan Luis Munoz Marin Intl

Tue 3/25

1:05 am-2:17 pm

2 stops13h 12m

$330

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 42 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.

Travel insights for flights from Virginia Beach to Caribbean

Get recent, data-driven insights about flights from Virginia Beach to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 20, 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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

LATAM Airlines
7.5
Good
1,795 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Spirit Airlines. According to our data, you can fly for as low as $59. Users have also found prices from $158 and $161 on Delta and Frontier, 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 March is currently the most expensive (average of $363). 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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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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$389FlexibilityNo cancel feeOn-time65%
FrontierCheapest$148Average$279FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$621FlexibilityNo cancel feeOn-time69%
DeltaCheapest$232Average$543FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$243Average$591FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$250Average$574FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$344Average$596FlexibilityNo cancel feeOn-time63%
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