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$111+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
May 10 — May 171
Sun 5/10
Sun 5/17
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 April 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/206:00 am
IAD
-
SJU
1 stop8h 13m
Frontier
Wed 4/223:19 pm
SJU
-
IAD
1 stop20h 16m
Frontier
Deal found 4/5$211
This Priceline deal was found by Cheapflights users on 4/6. 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.
Thu 4/3012:23 pm
IAD
-
SJU
1 stop10h 33m
Frontier
Mon 5/43:19 pm
SJU
-
IAD
1 stop26h 33m
Frontier
Deal found 4/6$212
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:37 pm
IAD
-
SJU
1 stop7h 31m
Frontier
Mon 5/116:25 pm
SJU
-
IAD
1 stop23h 27m
Frontier
Deal found 4/6$213
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 6/17:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Sun 6/76:00 am
SJU
-
IAD
1 stop13h 50m
Frontier
Deal found 4/6$214
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:59 pm
IAD
-
SJU
1 stop7h 58m
Frontier
Fri 5/296:00 am
SJU
-
IAD
1 stop13h 50m
Frontier
Deal found 4/7$215
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 5/210:51 am
IAD
-
SJU
2 stops25h 32m
Frontier
Wed 5/66:00 am
SJU
-
IAD
1 stop10h 22m
Frontier
Deal found 4/9$216
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 4/191:26 pm
IAD
-
SJU
1 stop9h 22m
Frontier
Wed 4/223:19 pm
SJU
-
IAD
1 stop20h 16m
Frontier
Deal found 4/5$219
This CheapOair deal was found by Cheapflights users on 4/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/87:27 pm
IAD
-
SJU
1 stop27h 16m
Frontier
Mon 5/116:25 pm
SJU
-
IAD
1 stop23h 27m
Frontier
Deal found 4/6$220
This Kiwi.com deal was found by Cheapflights users on 4/5. 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 5/19:37 pm
RDU
-
SJU
1 stop21h 45m
Multiple Airlines
Mon 5/43:03 am
SJU
-
RDU
1 stop6h 50m
Multiple Airlines
Deal found 4/5$220
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 4/287:15 am
IAD
-
SJU
2 stops15h 33m
Frontier
Fri 5/13:23 pm
SJU
-
IAD
1 stop9h 13m
Frontier
Deal found 4/6$221
This Super.com deal was found by Cheapflights users on 4/5. 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.
Mon 5/48:14 pm
RDU
-
SJU
Nonstop3h 29m
Frontier
Thu 5/77:00 am
SJU
-
RDU
Nonstop3h 57m
Frontier
Deal found 4/5$221
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/65:07 pm
IAD
-
SJU
1 stop9h 01m
Frontier
Wed 5/136:41 pm
SJU
-
IAD
2 stops21h 40m
Frontier
Deal found 4/6$222

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 April 10, 2026.

Round-trip from

$211
(Kiwi.com)

One-way from

$111
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$411

Good round-trip deal

$245 or less

Good one-way deal

$94 or less
From Virginia to Caribbean
Search Deals
One-way flight from Virginia 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 ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 10, 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.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Wed 4/22

7:06 am-2:48 pm

1 stop7h 42m

Saint Thomas Island Cyril E King

Wed 4/29

1:22 pm-12:42 am

1 stop11h 20m

$312

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Wed 6/17

2:36 pm-2:09 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Sun 6/21

5:15 pm-12:10 am

1 stop6h 55m

$321

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 4/27

4:30 pm-11:50 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Tue 5/19

1:00 am-8:20 am

1 stop7h 20m

$342

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 4/22

6:00 am-4:23 pm

1 stop10h 23m

San Juan Luis Munoz Marin Intl

Sat 4/25

6:15 am-2:05 pm

1 stop7h 50m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 6/8

5:00 pm-11:43 pm

1 stop6h 43m

San Juan Luis Munoz Marin Intl

Tue 6/16

12:54 pm-10:47 pm

1 stop9h 53m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 5/1

11:05 am-8:38 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Wed 5/20

1:00 am-10:23 am

1 stop9h 23m

$362

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 5/30

10:43 am-8:30 pm

1 stop9h 47m

San Juan Luis Munoz Marin Intl

Wed 6/10

5:56 pm-12:44 am

1 stop6h 48m

$362

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 6/4

9:00 am-8:30 pm

1 stop11h 30m

San Juan Luis Munoz Marin Intl

Wed 6/10

7:05 am-4:59 pm

1 stop9h 54m

$362

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 4/22

9:00 am-8:34 pm

2 stops11h 34m

San Juan Luis Munoz Marin Intl

Sun 4/26

1:00 am-9:30 am

1 stop8h 30m

$363

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 4/25

6:00 am-12:52 pm

1 stop6h 52m

San Juan Luis Munoz Marin Intl

Tue 4/28

12:55 pm-8:33 pm

1 stop7h 38m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

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, February is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $135). Flying from Virginia to Caribbean in March is currently the most expensive (average of $217). 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 April 10, 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 55% versus a flight in the morning.

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 20m. Delta provides one of the quickest options available for as low as $342. Virginia and Caribbean are separated by a distance of 1557 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 ($70), 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, February is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $135). Flying from Virginia to Caribbean in March is currently the most expensive (average of $217). 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 April 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$94Average$416FlexibilityNo cancel feeOn-time65%
FrontierCheapest$96Average$298FlexibilityNo cancel feeOn-time62%
DeltaCheapest$128Average$528FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$169Average$511FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$205Average$608FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$596FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$539FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$646Average$646FlexibilityNo cancel feeOn-time75%

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