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Caribbean

$105+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jun 27 — Jul 41
Sat 6/27
Sat 7/4
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 May 28, 2026.

This American Airlines deal was found by Cheapflights users on 5/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:11 pm
DCA
-
SJU
1 stop8h 48m
American Airlines
Wed 9/210:33 am
SJU
-
DCA
1 stop11h 27m
American Airlines
Deal found 5/27$271
This American Airlines deal was found by Cheapflights users on 5/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:23 pm
IAD
-
SJU
1 stop10h 36m
American Airlines
Fri 8/283:47 pm
SJU
-
IAD
1 stop7h 08m
American Airlines
Deal found 5/27$276
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:00 am
DCA
-
SJU
1 stop7h 48m
American Airlines
Thu 8/271:38 pm
SJU
-
DCA
1 stop7h 21m
American Airlines
Deal found 5/26$276
This deal was found by Cheapflights users on 5/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:15 am
RDU
-
SJU
1 stop8h 00m
Frontier
Tue 9/88:00 am
SJU
-
RDU
Nonstop3h 43m
Frontier
Deal found 5/26$279
This American Airlines deal was found by Cheapflights users on 5/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:57 am
IAD
-
SJU
1 stop16h 02m
American Airlines
Wed 8/263:47 pm
SJU
-
IAD
1 stop7h 08m
American Airlines
Deal found 5/27$281
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:44 pm
DCA
-
SJU
1 stop8h 11m
American Airlines
Wed 8/266:00 am
SJU
-
DCA
1 stop6h 38m
American Airlines
Deal found 5/26$281
This Frontier deal was found by Cheapflights users on 5/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:45 pm
RDU
-
SJU
1 stop8h 13m
Frontier
Wed 7/227:30 am
SJU
-
RDU
1 stop9h 59m
Frontier
Deal found 5/25$291
This Kiwi.com deal was found by Cheapflights users on 5/25. 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 7/86:14 pm
RDU
-
SJU
1 stop6h 14m
Frontier
Wed 7/155:15 pm
SJU
-
RDU
1 stop6h 49m
Frontier
Deal found 5/25$292
This Super.com deal was found by Cheapflights users on 5/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/1410:22 pm
RDU
-
SJU
1 stop16h 41m
Frontier
Tue 7/216:00 am
SJU
-
RDU
1 stop11h 09m
Frontier
Deal found 5/25$295
This Frontier deal was found by Cheapflights users on 5/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:46 pm
RDU
-
SJU
1 stop8h 11m
Frontier
Tue 7/145:15 pm
SJU
-
RDU
1 stop6h 49m
Frontier
Deal found 5/26$296
This Kiwi.com deal was found by Cheapflights users on 5/24. 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.
Tue 6/162:36 pm
RDU
-
SJU
1 stop8h 53m
Frontier
Wed 6/247:30 am
SJU
-
RDU
1 stop10h 13m
Frontier
Deal found 5/24$298
This Super.com deal was found by Cheapflights users on 5/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:56 pm
RDU
-
SJU
Nonstop3h 38m
Frontier
Tue 6/236:00 am
SJU
-
RDU
1 stop8h 26m
Frontier
Deal found 5/26$299

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 May 28, 2026.

Round-trip from

$271
(American Airlines)

One-way from

$105
(Super.com)

Popular in

December

Cheapest in

September

Average price

$352

Good round-trip deal

$285 or less

Good one-way deal

$148 or less
From Virginia to Caribbean
Search Deals
One-way flight from Virginia to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 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 May 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 May 28, 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

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 8/22

11:55 am-6:05 pm

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Thu 8/27

6:30 am-2:40 pm

2 stops8h 10m

$301

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Tue 7/7

8:23 pm-12:07 am

Nonstop3h 44m

San Juan Luis Munoz Marin Intl

Tue 7/14

8:37 pm-9:25 am

1 stop12h 48m

$309

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sat 6/6

6:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

Tue 6/9

1:00 am-8:56 am

1 stop7h 56m

$347

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Mon 6/8

7:53 pm-2:46 am

1 stop6h 53m

San Juan Luis Munoz Marin Intl

Fri 6/12

3:06 am-9:19 am

1 stop6h 13m

$350

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sat 7/4

6:27 pm-10:04 pm

Nonstop3h 37m

San Juan Luis Munoz Marin Intl

Wed 7/15

3:22 pm-7:01 pm

Nonstop3h 39m

$353

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 9/11

9:00 am-12:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sun 9/20

4:55 pm-8:47 pm

Nonstop3h 52m

$361

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 6/14

5:24 pm-9:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 6/19

1:25 pm-9:00 pm

1 stop7h 35m

$369

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 9/12

6:00 am-4:31 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Sat 9/19

12:58 pm-8:15 pm

1 stop7h 17m

$370

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 7/14

8:27 am-4:39 pm

1 stop8h 12m

San Juan Luis Munoz Marin Intl

Tue 7/28

5:50 pm-12:41 am

1 stop6h 51m

$370

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 7/13

7:28 pm-5:29 am

1 stop10h 01m

San Juan Luis Munoz Marin Intl

Thu 7/16

1:00 am-7:46 am

1 stop6h 46m

$370

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/22

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, April is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $438). Flying from Virginia to Caribbean in September is currently the most expensive (average of $711). 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 May 28, 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 52 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Virginia to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Caribbean. Price data was last updated on May 23, 2026.

Travelers seeking maximum savings on their Virginia to Caribbean flight should consider departing on Saturday at noon when fares are most often at their lowest. Thursday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 3h 44m. Southwest provides one of the quickest options available for as low as $309. 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 Spirit Airlines ($69), JetBlue ($84), and American Airlines ($98).

  • 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, April is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $438). Flying from Virginia to Caribbean in September is currently the most expensive (average of $711). 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 8 airlines flying from Virginia to Caribbean

Discover the top 8 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 May 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$94Average$425FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$107Average$510FlexibilityNo cancel feeOn-time62%
DeltaCheapest$112Average$504FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$124Average$301FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$205Average$603FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$589FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$541FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$646Average$646FlexibilityNo cancel feeOn-time75%

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