HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$102+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Virginia Beach to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 16, 2025.

This Frontier deal was found by Cheapflights users on 12/14. 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 12/222:04 pmORF - SJU
1 stop8h 34mFrontier
Thu 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/14$284
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:01 pmORF - SJU
1 stop6h 04mMultiple Airlines
Fri 1/99:23 pmSJU - ORF
1 stop25h 27mMultiple Airlines
Deal found 12/15$313
This Expedia deal was found by Cheapflights users on 12/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:01 pmORF - SJU
1 stop6h 04mSpirit Airlines
Thu 1/82:59 amSJU - ORF
2 stops16h 39mSpirit Airlines
Deal found 12/15$330
This Priceline deal was found by Cheapflights users on 12/14. 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.
Tue 12/233:11 pmORF - SJU
1 stop28h 16mFrontier
Wed 1/79:23 pmSJU - ORF
1 stop17h 11mFrontier
Deal found 12/14$343
This Frontier deal was found by Cheapflights users on 12/13. 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 12/213:09 pmORF - SJU
1 stop10h 41mFrontier
Thu 1/86:15 amSJU - ORF
1 stop8h 19mFrontier
Deal found 12/13$353
This Frontier deal was found by Cheapflights users on 12/13. 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.
Sat 12/203:01 pmORF - SJU
1 stop10h 49mFrontier
Sun 12/216:00 amSJU - ORF
1 stop9h 14mFrontier
Deal found 12/13$354
This Priceline deal was found by Cheapflights users on 12/16. 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.
Tue 12/233:11 pmORF - SJU
1 stop28h 16mFrontier
Mon 12/299:37 pmSJU - ORF
1 stop17h 39mFrontier
Deal found 12/16$364
This Priceline deal was found by Cheapflights users on 12/14. 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.
Sun 12/213:09 pmORF - SJU
1 stop7h 34mFrontier
Wed 1/79:23 pmSJU - ORF
1 stop17h 11mFrontier
Deal found 12/14$373
This Delta deal was found by Cheapflights users on 12/14. 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 12/158:30 amORF - MBJ
1 stop5h 43mDelta
Fri 12/192:29 pmMBJ - ORF
1 stop10h 03mDelta
Deal found 12/14$377
This Booking.com deal was found by Cheapflights users on 12/14. 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.
Mon 12/158:38 amORF - SJU
1 stop14h 38mMultiple Airlines
Mon 12/229:37 pmSJU - ORF
1 stop17h 39mMultiple Airlines
Deal found 12/14$379
This Priceline deal was found by Cheapflights users on 12/14. 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.
Mon 12/223:01 pmORF - SJU
1 stop6h 04mMultiple Airlines
Wed 1/79:23 pmSJU - ORF
1 stop17h 11mMultiple Airlines
Deal found 12/14$381
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/155:51 amORF - MBJ
2 stops9h 58mAmerican Airlines
Fri 12/194:11 pmMBJ - ORF
1 stop8h 48mAmerican Airlines
Deal found 12/14$382

Find 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 December 16, 2025.

Round-trip from

$250
(Kiwi.com)

One-way from

$102
(Priceline)

Popular in

December

Cheapest in

September

Average price

$583
From Virginia Beach to Caribbean
Search Deals
One-way flight from Virginia Beach to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 16, 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

Sat 1/24

5:30 pm-3:05 pm

2 stops20h 35m

Saint Thomas Island Cyril E King

Fri 1/30

3:57 pm-9:50 pm

1 stop6h 53m

$276

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Mon 2/2

6:45 am-2:52 pm

1 stop7h 07m

Saint Thomas Island Cyril E King

Fri 2/6

3:57 pm-9:50 pm

1 stop6h 53m

$284

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Fri 1/16

6:45 am-2:52 pm

1 stop7h 07m

Saint Thomas Island Cyril E King

Fri 1/23

3:57 pm-9:50 pm

1 stop6h 53m

$284

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 2/6

7:01 am-4:50 pm

1 stop8h 49m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:27 pm-12:16 am

1 stop6h 49m

$285

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 2/15

6:45 am-11:09 pm

1 stop15h 24m

San Juan Luis Munoz Marin Intl

Tue 2/17

4:36 pm-6:26 pm

1 stop26h 50m

$291

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 2/3

7:33 pm-9:47 am

2 stops13h 14m

San Juan Luis Munoz Marin Intl

Tue 2/17

9:29 pm-6:26 pm

2 stops21h 57m

$292

NorfolkMontego Bay

ORF - MBJ

ORFMBJ

Norfolk

Sat 2/28

8:34 pm-12:02 pm

1 stop15h 28m

Montego Bay Sangster Intl

Wed 3/4

1:00 pm-6:26 pm

1 stop5h 26m

$297

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Fri 5/1

1:50 pm-5:20 pm

Nonstop3h 30m

San Juan Luis Munoz Marin Intl

Mon 5/4

9:00 am-12:50 pm

Nonstop3h 50m

$298

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 1/27

8:50 am-7:05 pm

2 stops9h 15m

San Juan Luis Munoz Marin Intl

Thu 1/29

6:10 am-4:45 pm

2 stops11h 35m

$299

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Fri 2/20

6:45 am-2:31 pm

1 stop6h 46m

Saint Thomas Island Cyril E King

Sun 2/22

3:36 pm-9:50 pm

1 stop7h 14m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 60 results
1
2
3
...
6

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 $113). Flying from Virginia Beach to Caribbean in June is currently the most expensive (average of $208). 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 December 16, 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 at noon, which can drop the price by up to 25% 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 at noon 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 December 16, 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
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,049 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,186 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 3h 30m. Spirit Airlines provides one of the quickest options available for as low as $298. 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 Frontier. According to our data, you can fly for as low as $84. Users have also found prices from $105 and $112 on Spirit Airlines and American 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 - Saint Thomas Island Cyril E King 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 $113). Flying from Virginia Beach to Caribbean in June is currently the most expensive (average of $208). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Virginia Beach to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Cancún flights
Reagan-National to Miami flights
Dulles Intl to Miami flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to Orlando flights
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Las Vegas flights
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Fort Lauderdale flights
Reagan-National to Los Angeles flights
Reagan-National to Dallas/Fort Worth flights
Reagan-National to Orlando flights
Reagan-National to Cancún flights
Dulles Intl to Los Angeles flights
Reagan-National to Luis Munoz Marin Intl flights
Reagan-National to Las Vegas flights
Dulles Intl to Sky Harbor Intl flights
Dulles Intl to Heathrow flights
Raleigh to John F Kennedy Intl flights
Dulles Intl to Atlanta flights
Reagan-National to Hobby flights
Dulles Intl to Haneda flights
Dulles Intl to Hobby flights
Raleigh to LaGuardia flights
Dulles Intl to San Salvador flights
Dulles Intl to Tampa flights
Dulles Intl to Mexico City flights
Dulles Intl to New Orleans flights
Raleigh to Miami flights
Dulles Intl to Seattle flights
Reagan-National to Seattle flights
Dulles Intl to San Francisco flights
Dulles Intl to Charles de Gaulle flights
Dulles Intl to Denver flights
Reagan-National to Tampa flights
Reagan-National to Atlanta flights
Raleigh to Las Vegas flights
Raleigh to Luis Munoz Marin Intl flights
Reagan-National to San Francisco flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to O'Hare Intl flights
Reagan-National to New Orleans flights
Dulles Intl to Leonardo da Vinci/Fiumicino flights
Reagan-National to West Palm Beach flights
Dulles Intl to Narita flights
Reagan-National to Salt Lake City flights
Reagan-National to Sky Harbor Intl flights
Raleigh to Newark flights
Raleigh to Dallas/Fort Worth flights
Dulles Intl to Istanbul flights

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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$292FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$90Average$394FlexibilityNo cancel feeOn-time65%
DeltaCheapest$212Average$526FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$580FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$602FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$250Average$627FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$256Average$550FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.