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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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Round-trip from

$239
(Mytrip)

One-way from

$113
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$361
From Virginia Beach to Caribbean
Search Deals
One-way flight from Virginia Beach to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 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 October 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 October 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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.
Thu 11/209:26 pmORF - STT
1 stop16h 04mSpirit Airlines
Mon 11/243:25 pmSTT - ORF
1 stop6h 06mSpirit Airlines
Deal found 10/29$269
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 11/289:26 pmORF - STT
1 stop16h 04mSpirit Airlines
Fri 12/51:01 pmSTT - ORF
1 stop7h 15mSpirit Airlines
Deal found 10/29$283
This Frontier deal was found by Cheapflights users on 10/30. 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.
Mon 11/1011:42 amORF - SJU
2 stops14h 12mFrontier
Wed 11/123:59 amSJU - ORF
1 stop10h 16mFrontier
Deal found 10/30$283
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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.
Sun 11/167:53 pmORF - STT
1 stop16h 07mSpirit Airlines
Sun 11/233:25 pmSTT - ORF
1 stop6h 06mSpirit Airlines
Deal found 10/29$287
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/147:34 pmORF - SJU
1 stop13h 43mAmerican Airlines
Wed 11/196:25 amSJU - ORF
1 stop13h 11mAmerican Airlines
Deal found 10/29$290
This Priceline deal was found by Cheapflights users on 10/29. 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 11/132:00 pmORF - SJU
1 stop11h 54mFrontier
Sat 11/153:59 amSJU - ORF
1 stop9h 17mFrontier
Deal found 10/29$296
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/269:26 pmORF - SJU
1 stop22h 46mMultiple Airlines
Wed 12/39:15 amSJU - ORF
2 stops47h 28mMultiple Airlines
Deal found 10/29$300
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Tue 12/303:11 pmORF - SJU
1 stop28h 16mFrontier
Wed 1/213:55 amSJU - ORF
1 stop9h 20mFrontier
Deal found 10/30$313
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 11/101:19 pmORF - SJU
1 stop12h 35mMultiple Airlines
Mon 11/245:19 pmSJU - ORF
1 stop26h 48mMultiple Airlines
Deal found 10/29$314
This Frontier deal was found by Cheapflights users on 10/30. 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.
Sun 11/91:11 pmORF - SJU
1 stop12h 43mFrontier
Sat 11/153:59 amSJU - ORF
1 stop9h 17mFrontier
Deal found 10/30$316
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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.
Sun 12/148:11 pmORF - SJU
1 stop15h 21mSpirit Airlines
Fri 1/96:00 amSJU - ORF
1 stop9h 12mSpirit Airlines
Deal found 10/29$319
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/257:34 pmORF - SJU
1 stop13h 36mAmerican Airlines
Tue 12/26:25 amSJU - ORF
1 stop8h 14mAmerican Airlines
Deal found 10/28$321

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 October 30, 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

Thu 1/8

7:00 am-4:49 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:15 pm-9:30 pm

1 stop8h 15m

$247

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Thu 11/20

9:26 pm-2:30 pm

1 stop16h 04m

Saint Thomas Island Cyril E King

Mon 11/24

3:25 pm-8:31 pm

1 stop6h 06m

$269

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Fri 11/28

9:26 pm-2:30 pm

1 stop16h 04m

Saint Thomas Island Cyril E King

Fri 12/5

1:01 pm-7:16 pm

1 stop7h 15m

$283

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 1/27

10:05 am-9:00 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-2:07 pm

2 stops13h 02m

$315

NorfolkPunta Cana

ORF - PUJ

ORFPUJ

Norfolk

Wed 2/4

8:32 pm-12:54 pm

1 stop15h 22m

Punta Cana

Tue 2/10

1:49 pm-7:37 pm

1 stop6h 48m

$317

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Thu 2/19

8:09 pm-12:28 pm

1 stop15h 19m

Saint Thomas Island Cyril E King

Tue 2/24

1:33 pm-7:14 pm

1 stop6h 41m

$339

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 11/10

5:15 am-5:26 pm

1 stop11h 11m

San Juan Luis Munoz Marin Intl

Thu 11/13

3:20 pm-11:22 pm

1 stop9h 02m

$345

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 11/8

6:35 am-3:40 pm

1 stop8h 05m

San Juan Luis Munoz Marin Intl

Tue 11/11

2:05 am-10:42 am

1 stop9h 37m

$345

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 11/4

1:36 pm-10:59 pm

1 stop8h 23m

San Juan Luis Munoz Marin Intl

Tue 11/11

6:36 pm-12:13 am

1 stop6h 37m

$345

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 11/8

5:29 pm-1:15 am

1 stop6h 46m

San Juan Luis Munoz Marin Intl

Wed 11/12

7:15 am-5:32 pm

1 stop11h 17m

$345

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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, May is the cheapest month in which you can book a flight from Virginia Beach to Caribbean (average of $109). Flying from Virginia Beach to Caribbean in February is currently the most expensive (average of $230). 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 October 30, 2025.

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 in the evening, which can drop the price by up to 20% versus a flight in the afternoon.

What is the cheapest day to fly from Virginia Beach to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Virginia Beach to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Virginia Beach to Caribbean flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 30, 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
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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 49m. Delta provides one of the quickest options available for as low as $247. 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 $170 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 - 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, May is the cheapest month in which you can book a flight from Virginia Beach to Caribbean (average of $109). Flying from Virginia Beach to Caribbean in February is currently the most expensive (average of $230). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$309FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$429FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$208Average$593FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$537FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$242Average$612FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$614FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$266Average$566FlexibilityNo cancel feeOn-time62%

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