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$103+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jun 2 — Jun 91
Tue 6/2
Tue 6/9
1 adult, Economy
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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 May 3, 2026.

This SmartFares deal was found by Cheapflights users on 4/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/201:36 pm
ORF
-
SJU
Nonstop3h 59m
JetBlue
Mon 5/259:00 am
SJU
-
ORF
Nonstop3h 41m
JetBlue
Deal found 4/30$212
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/101:03 pm
ORF
-
SJU
Nonstop3h 56m
JetBlue
Sun 5/178:27 am
SJU
-
ORF
Nonstop3h 41m
JetBlue
Deal found 4/30$220
This Orbitz deal was found by Cheapflights users on 4/29. 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.
Sat 5/167:24 pm
ORF
-
SJU
1 stop12h 40m
Multiple Airlines
Wed 5/209:00 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 4/29$221
This JetBlue deal was found by Cheapflights users on 4/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/111:36 pm
ORF
-
SJU
Nonstop3h 59m
JetBlue
Fri 5/229:15 am
SJU
-
ORF
Nonstop3h 41m
JetBlue
Deal found 4/30$225
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:12 pm
ORF
-
SJU
1 stop28h 56m
Multiple Airlines
Wed 5/209:00 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 4/30$227
This Priceline deal was found by Cheapflights users on 5/1. 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 5/167:24 pm
ORF
-
SJU
1 stop6h 44m
Multiple Airlines
Mon 5/189:00 am
SJU
-
ORF
Nonstop3h 41m
Multiple Airlines
Deal found 5/1$229
This United Airlines deal was found by Cheapflights users on 5/2. 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 5/168:00 am
ORF
-
SJU
2 stops13h 24m
United Airlines
Wed 5/204:55 pm
SJU
-
ORF
1 stop6h 55m
United Airlines
Deal found 5/2$234
This Priceline deal was found by Cheapflights users on 5/1. 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 8/89:35 pm
ORF
-
SJU
1 stop10h 22m
Frontier
Tue 8/113:06 am
SJU
-
ORF
1 stop17h 33m
Frontier
Deal found 5/1$238
This Cheapflightsfares deal was found by Cheapflights users on 5/1. 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 5/151:36 pm
ORF
-
SJU
Nonstop3h 59m
JetBlue
Fri 5/229:15 am
SJU
-
ORF
Nonstop3h 41m
JetBlue
Deal found 5/1$240
This Priceline deal was found by Cheapflights users on 4/29. 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.
Tue 6/167:25 pm
ORF
-
SJU
1 stop6h 44m
Multiple Airlines
Mon 6/2211:41 am
SJU
-
ORF
Nonstop3h 33m
Multiple Airlines
Deal found 4/29$241
This Cheapflightsfares deal was found by Cheapflights users on 5/2. 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 5/151:36 pm
ORF
-
SJU
Nonstop3h 59m
JetBlue
Wed 5/209:00 am
SJU
-
ORF
Nonstop3h 41m
JetBlue
Deal found 5/2$245
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 6/59:12 pm
ORF
-
SJU
1 stop10h 52m
Frontier
Tue 6/97:00 am
SJU
-
ORF
2 stops28h 26m
Frontier
Deal found 4/27$248

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 May 3, 2026.

Round-trip from

$212
(SmartFares)

One-way from

$103
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$367
From Virginia Beach to Caribbean
Search Deals
One-way flight from Virginia Beach to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 3, 2026.
Use the filters below to find and compare flights from Virginia Beach to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sat 5/16

8:00 am-9:24 pm

2 stops13h 24m

San Juan Luis Munoz Marin Intl

Wed 5/20

4:55 pm-11:50 pm

1 stop6h 55m

$234
Quickest round-trip

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Mon 5/18

1:36 pm-5:35 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Fri 5/22

9:15 am-12:56 pm

Nonstop3h 41m

$245

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Thu 9/24

1:48 pm-10:00 pm

1 stop8h 12m

San Juan Luis Munoz Marin Intl

Tue 9/29

5:41 pm-12:06 am

1 stop6h 25m

$284

NorfolkSan Juan

ORF - SJU

ORFSJU

Norfolk

Sun 5/31

1:36 pm-5:37 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Mon 6/8

9:00 am-12:41 pm

Nonstop3h 41m

$299

NorfolkNassau

ORF - NAS

ORFNAS

Norfolk

Tue 6/2

6:05 am-3:56 pm

1 stop9h 51m

Nassau Intl

Mon 6/8

3:59 pm-12:57 am

1 stop8h 58m

$314

NorfolkNassau

ORF - NAS

ORFNAS

Norfolk

Sat 7/4

12:33 pm-4:59 pm

1 stop4h 26m

Nassau Intl

Wed 7/8

12:08 pm-9:02 pm

1 stop8h 54m

$314

NorfolkNassau

ORF - NAS

ORFNAS

Norfolk

Sat 5/30

8:00 am-2:57 pm

1 stop6h 57m

Nassau Intl

Thu 6/4

3:59 pm-12:57 am

1 stop8h 58m

$314

NorfolkNassau

ORF - NAS

ORFNAS

Norfolk

Sun 7/19

6:20 am-4:39 pm

1 stop10h 19m

Nassau Intl

Tue 7/28

1:16 pm-12:45 am

1 stop11h 29m

$326

NorfolkNassau

ORF - NAS

ORFNAS

Norfolk

Mon 6/8

6:00 am-2:57 pm

1 stop8h 57m

Nassau Intl

Fri 6/12

12:35 pm-11:44 pm

2 stops11h 09m

$327

NorfolkSimpson Bay

ORF - SXM

ORFSXM

Norfolk

Thu 7/23

7:59 pm-1:46 pm

1 stop17h 47m

Simpson Bay Princess Juliana

Tue 7/28

2:51 pm-11:42 pm

1 stop8h 51m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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 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 May 3, 2026.

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 55% versus a flight in the morning.

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 May 3, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
4,310 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,310 reviews
Southwest
8.0
Very good
4,310 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,460 reviews
Southwest
8.0
Very good
4,310 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,682 reviews
Southwest
8.0
Very good
4,310 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,674 reviews
Southwest
8.0
Very good
4,310 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.1
Good
2,966 reviews
Southwest
8.0
Very good
4,310 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 59m. United Airlines provides one of the quickest options available for as low as $245. 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 JetBlue. According to our data, you can fly for as low as $70. Users have also found prices from $102 and $112 on Southwest 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.

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

    On average you can expect to pay $290 for a flight from Virginia Beach to Caribbean. The cheapest flight overall is $122 while the most popular route, (Norfolk - San Juan Luis Munoz Marin Intl) is currently priced at $220.

  • 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.

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 8 airlines flying from Virginia Beach to Caribbean

Discover the top 8 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 May 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$94Average$407FlexibilityNo cancel feeOn-time65%
FrontierCheapest$96Average$297FlexibilityNo cancel feeOn-time62%
DeltaCheapest$112Average$497FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$172Average$518FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$205Average$618FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$557FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$537FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$646Average$646FlexibilityNo cancel feeOn-time75%

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