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Caribbean

$125+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
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 29, 2026.

This Frontier deal was found by Cheapflights users on 7/28. 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.
Tue 8/48:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Tue 8/118:37 pm
SJU
-
RDU
1 stop12h 48m
Frontier
Deal found 7/28$277
This FlightHub deal was found by Cheapflights users on 7/27. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Sun 8/238:57 pm
SJU
-
RDU
1 stop14h 38m
Frontier
Deal found 7/27$280
This Frontier deal was found by Cheapflights users on 7/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:05 am
RDU
-
SJU
1 stop8h 11m
Frontier
Wed 8/268:57 pm
SJU
-
RDU
1 stop11h 21m
Frontier
Deal found 7/27$281
This Frontier deal was found by Cheapflights users on 7/27. 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 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 7/27$282
This Kiwi.com deal was found by Cheapflights users on 7/26. 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.
Sat 8/1510:34 pm
RDU
-
SJU
1 stop26h 07m
Frontier
Sat 8/225:37 pm
SJU
-
RDU
2 stops30h 22m
Frontier
Deal found 7/26$283
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/68:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Mon 8/1010:48 pm
SJU
-
RDU
1 stop10h 37m
Frontier
Deal found 7/25$284
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 9/74:02 pm
RDU
-
SJU
2 stops32h 54m
Frontier
Mon 9/144:39 pm
SJU
-
RDU
1 stop24h 20m
Frontier
Deal found 7/24$285
This Super.com deal was found by Cheapflights users on 7/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:56 pm
RDU
-
SJU
Nonstop3h 38m
JetBlue
Mon 8/243:22 pm
SJU
-
RDU
Nonstop3h 39m
JetBlue
Deal found 7/28$286
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 8/215:55 pm
RDU
-
SJU
1 stop7h 01m
Frontier
Sun 8/235:15 pm
SJU
-
RDU
1 stop23h 55m
Frontier
Deal found 7/26$287
This Kiwi.com deal was found by Cheapflights users on 7/24. 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 8/136:15 am
RDU
-
SJU
2 stops13h 17m
Frontier
Thu 8/203:28 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 7/24$288
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Wed 8/55:49 pm
RDU
-
SJU
1 stop14h 08m
Frontier
Thu 8/63:36 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 7/24$289
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Wed 8/195:58 pm
RDU
-
SJU
1 stop8h 17m
Frontier
Sun 8/233:10 am
SJU
-
RDU
1 stop8h 25m
Frontier
Deal found 7/25$290

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 29, 2026.

Round-trip from

$277
(American Airlines)

One-way from

$125
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$426

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 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 29, 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

Tue 9/8

3:35 pm-10:05 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Tue 9/15

5:15 am-2:55 pm

2 stops9h 40m

$293

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/28

5:40 pm-11:45 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Tue 11/3

5:50 pm-10:55 pm

1 stop6h 05m

$306

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 11/2

4:55 pm-12:55 am

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Fri 11/6

4:00 pm-10:40 pm

1 stop7h 40m

$306

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 8/29

6:15 am-1:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Sat 9/5

4:55 pm-8:47 pm

Nonstop3h 52m

$312

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 8/24

5:05 pm-11:50 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Fri 8/28

6:30 am-2:40 pm

2 stops8h 10m

$316

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 8/25

6:00 am-1:35 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Fri 8/28

6:30 am-2:40 pm

2 stops8h 10m

$316

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 8/25

6:15 am-2:44 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Fri 8/28

4:55 pm-8:47 pm

Nonstop3h 52m

$322

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 8/26

3:03 pm-10:29 pm

1 stop7h 26m

San Juan Luis Munoz Marin Intl

Wed 9/2

5:49 pm-12:34 am

1 stop6h 45m

$326

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 10/2

6:45 am-1:45 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Mon 10/5

3:56 pm-12:58 am

1 stop9h 02m

$326

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 8/17

4:30 pm-11:50 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 8/18

1:00 am-7:49 am

1 stop6h 49m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

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 July 29, 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 6h 30m. Southwest provides one of the quickest options available for as low as $293. 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), JetBlue ($87), 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 $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

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Alternative routes for Virginia to Caribbean

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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 29, 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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