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Caribbean

$120+ Cheap flights from Virginia 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Sep 2 — Sep 91
Wed 9/2
Wed 9/9
1 adult, Economy
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Cheap flight deals from Virginia to Caribbean

Cheapest flights from Virginia to Caribbean
Explore the most affordable flight options available from Virginia to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.

This Delta deal was found by Cheapflights users on 8/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:15 am
RDU
-
SJU
1 stop6h 30m
Delta
Thu 12/107:00 am
SJU
-
RDU
1 stop7h 55m
Delta
Deal found 8/1$272
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:55 pm
RDU
-
SJU
1 stop7h 01m
Frontier
Tue 8/253:10 am
SJU
-
RDU
1 stop6h 42m
Frontier
Deal found 8/2$273
This JetBlue deal was found by Cheapflights users on 7/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:15 am
RDU
-
SJU
1 stop8h 38m
JetBlue
Tue 9/87:00 am
SJU
-
RDU
1 stop6h 05m
JetBlue
Deal found 7/29$274
This Kiwi.com deal was found by Cheapflights users on 7/31. 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 8/168:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Wed 8/198:57 pm
SJU
-
RDU
1 stop11h 21m
Frontier
Deal found 7/31$275
This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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.
Fri 8/2810:53 am
RDU
-
SJU
1 stop8h 00m
JetBlue
Fri 9/45:05 am
SJU
-
RDU
1 stop8h 00m
JetBlue
Deal found 7/30$276
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:20 am
RDU
-
SJU
2 stops9h 51m
American Airlines
Sun 8/306:00 am
SJU
-
RDU
1 stop15h 12m
American Airlines
Deal found 7/30$277
This JetBlue deal was found by Cheapflights users on 8/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/232:50 pm
RDU
-
SJU
1 stop5h 37m
JetBlue
Thu 8/275:05 am
SJU
-
RDU
1 stop8h 00m
JetBlue
Deal found 8/2$278
This Kiwi.com deal was found by Cheapflights users on 8/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:32 pm
RDU
-
SJU
1 stop6h 43m
Frontier
Mon 8/1710:48 pm
SJU
-
RDU
1 stop11h 04m
Frontier
Deal found 8/1$279
This Frontier deal was found by Cheapflights users on 7/31. 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.
Wed 8/198:16 pm
RDU
-
SJU
1 stop11h 55m
Frontier
Sun 8/233:28 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 7/31$280
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sun 8/98:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Mon 8/173:10 am
SJU
-
RDU
1 stop6h 42m
Frontier
Deal found 7/30$281
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 8/2010:11 pm
RDU
-
SJU
2 stops26h 45m
Frontier
Thu 9/107:00 am
SJU
-
RDU
1 stop9h 31m
Frontier
Deal found 7/30$282
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1110:22 pm
RDU
-
SJU
1 stop12h 54m
Frontier
Wed 8/123:10 am
SJU
-
RDU
1 stop6h 25m
Frontier
Deal found 8/2$283

Find flight deals from Virginia to Caribbean

Keep the following information in mind while searching for Virginia to Caribbean flight deals. Data was last updated August 3, 2026.

Round-trip from

$272
(Delta)

One-way from

$120
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$359

Good round-trip deal

$277 or less

Good one-way deal

$132 or less
From Virginia to Caribbean
Search Deals
One-way flight from Virginia to Caribbean
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Virginia to Caribbean.
Search Deals
Price to beat on a one-way flight from Virginia to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia 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 August 3, 2026.
Use the filters below to find and compare flights from Virginia to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Mon 8/24

10:16 am-5:33 pm

1 stop7h 17m

San Juan Luis Munoz Marin Intl

Fri 8/28

1:48 pm-9:19 pm

1 stop7h 31m

$278

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sun 8/23

6:20 am-12:48 pm

1 stop6h 28m

San Juan Luis Munoz Marin Intl

Fri 8/28

7:00 am-1:05 pm

1 stop6h 05m

$278
Quickest round-trip

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Wed 8/19

7:56 pm-11:34 pm

Nonstop3h 38m

San Juan Luis Munoz Marin Intl

Wed 8/26

3:22 pm-7:01 pm

Nonstop3h 39m

$303

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sat 8/22

6:44 pm-10:24 pm

Nonstop3h 40m

San Juan Luis Munoz Marin Intl

Thu 8/27

3:22 pm-7:01 pm

Nonstop3h 39m

$303

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Wed 8/19

7:56 pm-11:34 pm

Nonstop3h 38m

San Juan Luis Munoz Marin Intl

Tue 8/25

1:48 pm-9:19 pm

1 stop7h 31m

$308

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 8/29

6:30 am-3:42 pm

1 stop9h 12m

San Juan Luis Munoz Marin Intl

Wed 9/2

4:55 pm-8:47 pm

Nonstop3h 52m

$312

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 8/30

6:30 am-3:42 pm

1 stop9h 12m

San Juan Luis Munoz Marin Intl

Tue 9/1

3:56 pm-12:44 am

1 stop8h 48m

$320

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 9/1

9:00 am-12:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Tue 9/15

3:56 pm-12:44 am

1 stop8h 48m

$322

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 8/31

12:29 pm-11:52 pm

1 stop11h 23m

San Juan Luis Munoz Marin Intl

Fri 9/4

2:59 pm-12:34 am

1 stop9h 35m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 10/30

3:25 pm-1:20 am

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Mon 11/2

5:35 am-3:40 pm

2 stops11h 05m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Virginia to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Virginia 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 to Caribbean

What is the cheapest month to book a flight from Virginia to Caribbean?

Currently, January is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $445). Flying from Virginia to Caribbean in December is currently the most expensive (average of $619). 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 VA to CB?

Find hourly flight availability from Virginia 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 August 3, 2026.

When flying from Virginia 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 30% versus a flight in the morning.

How far ahead should I book a flight from Virginia to Caribbean?

The price you pay for your flight from Virginia to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

Related info for your journey

Find useful and relevant information for your journey from Virginia 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 to Caribbean?

    A quick flight from Virginia to Caribbean can take about 7h 17m. JetBlue provides one of the quickest options available for as low as $278. Virginia and Caribbean are separated by a distance of 1435 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Virginia to Caribbean one-way?

    The cheapest airlines for a one-way flight from Virginia to Caribbean are Southwest ($72), Frontier ($77), and JetBlue ($87).

  • Can I find deals for flights from Virginia to Caribbean that include hotel bookings?

    Yes. In addition to deals on Virginia to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia to Caribbean.

  • Can I find deals for business class flights from Virginia to Caribbean?

    Yes. Cheapflights offers flight deals from Virginia 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 to Caribbean?

    Currently, January is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $445). Flying from Virginia to Caribbean in December is currently the most expensive (average of $619). 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 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 to Caribbean

Discover the top 7 airlines that operate flights from Virginia 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 August 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$96Average$343FlexibilityNo cancel feeOn-time62%
DeltaCheapest$112Average$531FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$177Average$512FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$205Average$603FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$595FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$550FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$646Average$646FlexibilityNo cancel feeOn-time75%

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