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Caribbean

$121+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
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 July 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/22. 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 9/36:05 am
RDU
-
SJU
2 stops12h 44m
Multiple Airlines
Tue 9/154:39 pm
SJU
-
RDU
1 stop16h 20m
Multiple Airlines
Deal found 7/22$285
This FlightHub deal was found by Cheapflights users on 7/22. 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.
Thu 7/308:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Sun 8/23:36 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 7/22$287
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/285:55 pm
RDU
-
SJU
1 stop7h 01m
Frontier
Mon 8/318:57 pm
SJU
-
RDU
1 stop12h 55m
Frontier
Deal found 7/22$288
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/118:56 am
RDU
-
SJU
1 stop7h 15m
Frontier
Fri 8/1410:48 pm
SJU
-
RDU
1 stop10h 28m
Frontier
Deal found 7/21$289
This Frontier deal was found by Cheapflights users on 7/22. 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 8/98:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Sun 8/163:36 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 7/22$290
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/28:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Thu 8/66:00 am
SJU
-
RDU
1 stop11h 15m
Frontier
Deal found 7/22$291
This SmartFares deal was found by Cheapflights users on 7/19. 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.
Tue 8/187:56 pm
RDU
-
SJU
Nonstop3h 38m
JetBlue
Tue 8/253:22 pm
SJU
-
RDU
Nonstop3h 39m
JetBlue
Deal found 7/19$292
This Southwest deal was found by Cheapflights users on 7/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:55 am
RDU
-
SJU
2 stops8h 05m
Southwest
Wed 8/266:00 am
SJU
-
RDU
1 stop8h 55m
Southwest
Deal found 7/19$293
This Kiwi.com deal was found by Cheapflights users on 7/21. 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 8/102:31 pm
RDU
-
SJU
1 stop7h 12m
Frontier
Fri 8/1410:48 pm
SJU
-
RDU
1 stop10h 28m
Frontier
Deal found 7/21$294
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/47:05 am
RDU
-
SJU
1 stop6h 55m
Multiple Airlines
Tue 8/118:37 pm
SJU
-
RDU
1 stop12h 48m
Multiple Airlines
Deal found 7/20$295
This Frontier deal was found by Cheapflights users on 7/18. 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 11/118:30 am
RDU
-
SJU
1 stop6h 55m
Frontier
Wed 11/185:30 pm
SJU
-
RDU
1 stop7h 47m
Frontier
Deal found 7/18$296
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 8/176:09 pm
IAD
-
SJU
1 stop22h 02m
Frontier
Fri 8/213:10 am
SJU
-
IAD
2 stops14h 04m
Frontier
Deal found 7/22$303

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 July 23, 2026.

Round-trip from

$285
(Kiwi.com)

One-way from

$121
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$428

Good round-trip deal

$266 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. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 23, 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

Wed 8/19

10:55 am-7:00 pm

2 stops8h 05m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:00 am-2:55 pm

1 stop8h 55m

$293

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 8/25

6:00 am-12:20 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:45 pm-11:55 pm

1 stop6h 10m

$306

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 8/27

12:15 pm-10:10 pm

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Wed 9/2

1:20 pm-11:05 pm

2 stops9h 45m

$316

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 8/28

6:16 am-1:45 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Tue 9/1

4:55 pm-8:47 pm

Nonstop3h 52m

$322

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 9/9

12:49 pm-11:50 pm

2 stops11h 01m

San Juan Luis Munoz Marin Intl

Tue 9/15

4:20 pm-10:59 pm

1 stop6h 39m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 8/26

2:59 pm-11:50 pm

1 stop8h 51m

San Juan Luis Munoz Marin Intl

Sat 8/29

1:00 am-7:49 am

1 stop6h 49m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 9/24

12:55 pm-10:10 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Tue 9/29

1:20 pm-11:05 pm

2 stops9h 45m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/7

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Sat 10/10

1:00 am-7:49 am

1 stop6h 49m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 10/2

1:35 pm-11:05 pm

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Mon 10/5

5:00 am-11:20 am

1 stop6h 20m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 9/22

6:30 am-2:44 pm

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Tue 9/29

7:00 am-4:13 pm

1 stop9h 13m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

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 $447). Flying from Virginia to Caribbean in December is currently the most expensive (average of $622). 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 July 23, 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 5h 51m. Southwest provides one of the quickest options available for as low as $392. Virginia and Caribbean are separated by a distance of 960 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 JetBlue ($87), Southwest ($92), and Delta ($94).

  • 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 $447). Flying from Virginia to Caribbean in December is currently the most expensive (average of $622). 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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$96Average$360FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$107Average$505FlexibilityNo cancel feeOn-time62%
DeltaCheapest$112Average$528FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$205Average$602FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$594FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$552FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$646Average$646FlexibilityNo cancel feeOn-time75%

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