HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$77+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:45 am
ORF
-
STT
1 stop6h 46m
Spirit Airlines
Thu 3/53:36 pm
STT
-
ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/29$190
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:45 am
ORF
-
STT
1 stop6h 46m
Spirit Airlines
Sat 2/213:36 pm
STT
-
ORF
1 stop7h 14m
Spirit Airlines
Deal found 1/28$201
This CheapOair deal was found by Cheapflights users on 1/27. 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 2/197:31 pm
ORF
-
STT
1 stop20h 03m
Spirit Airlines
Tue 2/245:40 pm
STT
-
ORF
1 stop25h 46m
Spirit Airlines
Deal found 1/27$208
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
ORF
-
STT
2 stops27h 55m
Multiple Airlines
Mon 3/25:40 pm
STT
-
ORF
1 stop25h 46m
Multiple Airlines
Deal found 1/26$209
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sat 2/79:10 pm
ORF
-
SJU
1 stop26h 58m
Multiple Airlines
Wed 2/114:40 pm
SJU
-
ORF
2 stops19h 11m
Multiple Airlines
Deal found 1/27$209
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:43 pm
ORF
-
SJU
1 stop15h 11m
Multiple Airlines
Fri 4/249:00 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 1/28$211
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:43 pm
ORF
-
SJU
1 stop7h 18m
Frontier
Mon 5/46:30 am
SJU
-
ORF
1 stop11h 19m
Frontier
Deal found 1/28$212
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 2/811:45 am
ORF
-
SJU
1 stop26h 27m
Multiple Airlines
Thu 2/124:36 pm
SJU
-
ORF
1 stop26h 50m
Multiple Airlines
Deal found 1/27$213
This CheapOair deal was found by Cheapflights users on 1/27. 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.
Mon 2/238:49 am
ORF
-
SJU
1 stop14h 54m
Frontier
Fri 2/273:53 am
SJU
-
ORF
1 stop12h 59m
Frontier
Deal found 1/27$214
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:31 pm
ORF
-
STT
1 stop20h 03m
Spirit Airlines
Fri 2/275:40 pm
STT
-
ORF
1 stop27h 09m
Spirit Airlines
Deal found 1/28$215
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:45 am
ORF
-
SJU
1 stop15h 24m
Multiple Airlines
Fri 3/63:58 am
SJU
-
ORF
1 stop11h 33m
Multiple Airlines
Deal found 1/29$215
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/611:43 am
ORF
-
SJU
1 stop21h 56m
Multiple Airlines
Tue 2/106:00 am
SJU
-
ORF
1 stop7h 05m
Multiple Airlines
Deal found 1/26$216

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 January 29, 2026.

Round-trip from

$190
(Travelocity)

One-way from

$77
(Frontier)

Popular in

December

Cheapest in

September

Average price

$375
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 ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Thu 2/26

6:45 am-2:31 pm

1 stop6h 46m

Saint Thomas Island Cyril E King

Thu 3/5

3:36 pm-9:50 pm

1 stop7h 14m

$190

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Sat 2/14

6:45 am-2:31 pm

1 stop6h 46m

Saint Thomas Island Cyril E King

Sat 2/21

3:36 pm-9:50 pm

1 stop7h 14m

$201

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Mon 2/23

11:39 am-4:34 pm

2 stops27h 55m

Saint Thomas Island Cyril E King

Mon 3/2

5:40 pm-6:26 pm

1 stop25h 46m

$209

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Mon 4/20

8:24 pm-3:34 pm

1 stop19h 10m

Saint Thomas Island Cyril E King

Wed 4/29

4:40 pm-7:29 pm

1 stop26h 49m

$215

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Wed 2/25

7:31 pm-2:31 pm

2 stops18h 00m

Saint Thomas Island Cyril E King

Wed 3/4

5:40 pm-6:26 pm

1 stop25h 46m

$222

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 2/17

3:30 pm-11:58 pm

1 stop7h 28m

San Juan Luis Munoz Marin Intl

Tue 2/24

6:37 pm-12:14 am

1 stop6h 37m

$226

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 3/24

5:13 pm-11:15 pm

1 stop6h 02m

San Juan Luis Munoz Marin Intl

Tue 3/31

7:00 am-5:19 pm

1 stop10h 19m

$226

NorfolkSaint Thomas Island

ORF - STT

ORFSTT

Norfolk

Sun 2/22

7:31 pm-2:31 pm

2 stops18h 00m

Saint Thomas Island Cyril E King

Fri 2/27

5:40 pm-7:49 pm

1 stop27h 09m

$229

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Tue 3/3

10:15 am-9:00 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Tue 3/10

7:05 am-9:14 pm

2 stops14h 09m

$231

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 2/26

6:45 am-11:09 pm

1 stop15h 24m

San Juan Luis Munoz Marin Intl

Mon 3/2

3:53 am-12:05 pm

1 stop9h 12m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 $212). 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.

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 January 29, 2026.
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
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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
8,393 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

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 6h 46m. Spirit Airlines provides one of the quickest options available for as low as $190. The distance from Virginia Beach to Caribbean is about 1451 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 $103 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 - Montego Bay Sangster Intl when deciding on the best route from Virginia Beach to Caribbean.

  • What are the cheapest flights from Virginia Beach to Caribbean?

    On average you can expect to pay $429 for a flight from Virginia Beach to Caribbean. The cheapest flight overall is $245 while the most popular route, (Norfolk - San Juan Luis Munoz Marin Intl) is currently priced at $179.

  • 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 $212). 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 Miami flights
Reagan-National to Miami flights
Dulles Intl to Cancún flights
Dulles Intl to Orlando flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to Las Vegas flights
Dulles Intl to Dallas/Fort Worth flights
Reagan-National to Orlando flights
Dulles Intl to Los Angeles flights
Reagan-National to Los Angeles flights
Reagan-National to Fort Lauderdale flights
Dulles Intl to Tampa flights
Reagan-National to Las Vegas flights
Dulles Intl to Sky Harbor Intl flights
Dulles Intl to Luis Munoz Marin Intl flights
Dulles Intl to Seattle flights
Reagan-National to Hobby flights
Dulles Intl to Atlanta flights
Reagan-National to Seattle flights
Reagan-National to Cancún flights
Reagan-National to Dallas/Fort Worth flights
Reagan-National to San Francisco flights
Dulles Intl to Heathrow flights
Reagan-National to Luis Munoz Marin Intl flights
Raleigh to Miami flights
Dulles Intl to Denver flights
Dulles Intl to Hobby flights
Reagan-National to O'Hare Intl flights
Raleigh to Newark flights
Dulles Intl to New Orleans flights
Reagan-National to Tampa flights
Dulles Intl to San Francisco flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Salt Lake City flights
Reagan-National to Atlanta flights
Reagan-National to George Bush Intcntl flights
Dulles Intl to Charles de Gaulle flights
Reagan-National to Denver flights
Dulles Intl to Haneda flights
Raleigh to John F Kennedy Intl flights
Raleigh to Las Vegas flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to West Palm Beach flights
Dulles Intl to Fort Myers flights
Dulles Intl to Austin flights
Dulles Intl to Mexico City flights
Reagan-National to Sky Harbor Intl flights
Dulles Intl to Leonardo da Vinci/Fiumicino flights
Reagan-National to Salt Lake City flights
Dulles Intl to Boston 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$90Average$390FlexibilityNo cancel feeOn-time65%
DeltaCheapest$146Average$536FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$204Average$543FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$225Average$575FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$595FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$245Average$648FlexibilityNo cancel feeOn-time63%

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.