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$100+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Round-trip from

$217
(Mytrip)

One-way from

$100
(Cheapflightsfares)

Popular in

December

Cheapest in

July

Average price

$437
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 ($43 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 March 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 March 28, 2025.

This Mytrip deal was found by Cheapflights users on 3/27. 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.
Tue 4/2212:20 pmORF - STT
2 stops21h 40mSpirit Airlines
Tue 4/2911:05 amSTT - ORF
1 stop13h 14mSpirit Airlines
Deal found 3/27$217
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Mon 4/146:13 pmORF - SJU
1 stop23h 20mSpirit Airlines
Tue 4/228:45 pmSJU - ORF
2 stops27h 34mSpirit Airlines
Deal found 3/27$237
This Delta deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/227:00 amORF - SJU
1 stop9h 18mDelta
Tue 9/305:19 pmSJU - ORF
1 stop6h 47mDelta
Deal found 3/27$245
This American Airlines deal was found by Cheapflights users on 3/27. 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 9/166:50 amORF - SJU
1 stop5h 55mAmerican Airlines
Tue 9/238:30 amSJU - ORF
2 stops9h 43mAmerican Airlines
Deal found 3/27$265
This Priceline deal was found by Cheapflights users on 3/27. 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.
Sat 4/57:41 pmORF - SJU
1 stop6h 11mMultiple Airlines
Sat 4/122:45 amSJU - ORF
1 stop13h 52mMultiple Airlines
Deal found 3/27$274
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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.
Wed 4/166:00 amORF - PUJ
1 stop8h 13mSpirit Airlines
Wed 4/233:18 pmPUJ - ORF
1 stop9h 01mSpirit Airlines
Deal found 3/26$292
This United Airlines deal was found by Cheapflights users on 3/27. 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 11/15:12 pmORF - SJU
1 stop6h 24mUnited Airlines
Tue 11/42:05 amSJU - ORF
1 stop7h 50mUnited Airlines
Deal found 3/27$305
This CheapOair deal was found by Cheapflights users on 3/27. 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 4/35:41 pmORF - SJU
1 stop28h 05mFrontier
Sun 4/69:35 pmSJU - ORF
1 stop19h 23mFrontier
Deal found 3/27$308
This FlightHub deal was found by Cheapflights users on 3/26. 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 4/276:00 amORF - MBJ
1 stop5h 55mSpirit Airlines
Sat 5/312:00 pmMBJ - ORF
1 stop11h 19mSpirit Airlines
Deal found 3/26$314
This American Airlines deal was found by Cheapflights users on 3/26. 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 8/226:59 pmORF - STT
2 stops17h 41mAmerican Airlines
Wed 8/275:25 pmSTT - ORF
2 stops16h 05mAmerican Airlines
Deal found 3/26$391
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/43:01 pmORF - PUJ
2 stops22h 33mMultiple Airlines
Tue 4/83:47 pmPUJ - ORF
1 stop25h 31mMultiple Airlines
Deal found 3/27$411
This FlightHub deal was found by Cheapflights users on 3/27. 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.
Fri 4/118:45 pmORF - SXM
2 stops17h 15mSpirit Airlines
Mon 4/143:05 pmSXM - ORF
1 stop9h 14mSpirit Airlines
Deal found 3/27$414

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 28, 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

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Tue 4/22

12:20 pm-10:00 am

2 stops21h 40m

Saint Thomas Island Cyril E King

Tue 4/29

11:05 am-12:19 am

1 stop13h 14m

$217

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 4/14

6:13 pm-5:33 pm

1 stop23h 20m

San Juan Luis Munoz Marin Intl

Tue 4/22

8:45 pm-12:19 am

2 stops27h 34m

$237

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 4/29

11:39 am-8:28 pm

2 stops8h 49m

San Juan Luis Munoz Marin Intl

Tue 5/6

5:25 am-2:44 pm

2 stops9h 19m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 4/5

7:41 pm-1:52 am

1 stop6h 11m

San Juan Luis Munoz Marin Intl

Sat 4/12

2:45 am-4:37 pm

1 stop13h 52m

$274

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Wed 4/16

6:00 am-2:13 pm

1 stop8h 13m

Punta Cana

Wed 4/23

3:18 pm-12:19 am

1 stop9h 01m

$292

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 4/3

5:41 pm-9:46 pm

1 stop28h 05m

San Juan Luis Munoz Marin Intl

Sun 4/6

9:35 pm-4:58 pm

1 stop19h 23m

$308

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sun 4/27

6:00 am-10:55 am

1 stop5h 55m

Montego Bay Sangster Intl

Sat 5/3

12:00 pm-12:19 am

1 stop11h 19m

$314

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Wed 5/7

5:35 am-11:40 am

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Wed 5/21

7:00 am-5:00 pm

1 stop10h 00m

$325

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Fri 8/22

6:59 pm-12:40 pm

2 stops17h 41m

Saint Thomas Island Cyril E King

Wed 8/27

5:25 pm-9:30 am

2 stops16h 05m

$391

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 4/3

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Tue 4/8

1:05 am-2:26 pm

2 stops13h 21m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 57 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 March 28, 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 March 28, 2025.
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

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
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

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
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

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.
Copa Airlines
7.5
Good
1,395 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

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
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

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.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,274 reviews

Boarding

8.2

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

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 Spirit Airlines. According to our data, you can fly for as low as $100. Users have also found prices from $150 and $157 on American Airlines 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 - Montego Bay Sangster 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$390FlexibilityNo cancel feeOn-time65%
FrontierCheapest$135Average$297FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$625FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$610FlexibilityNo cancel feeOn-time71%
DeltaCheapest$232Average$527FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$256Average$579FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$349Average$611FlexibilityNo cancel feeOn-time63%
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