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$77+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Feb 11 — Feb 181
Wed 2/11
Wed 2/18
1 adult, Economy
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Cheap flight deals from Virginia to Caribbean

Keep the following information in mind while searching for Virginia to Caribbean flight deals. Data was last updated January 12, 2026.

Round-trip from

$150
(Super.com)

One-way from

$77
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$368

Good round-trip deal

$271 or less
From Virginia to Caribbean
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One-way flight from Virginia to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Virginia to Caribbean.
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Find 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 January 12, 2026.

This Super.com deal was found by Cheapflights users on 1/11. 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.
Sun 3/18:20 pm
RDU
-
SJU
Nonstop3h 21m
Frontier
Sat 3/710:12 pm
SJU
-
RDU
1 stop8h 48m
Frontier
Deal found 1/11$150
This Frontier deal was found by Cheapflights users on 1/11. 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 2/115:54 pm
RDU
-
SJU
1 stop7h 59m
Frontier
Tue 2/173:53 am
SJU
-
RDU
1 stop11h 05m
Frontier
Deal found 1/11$154
This CheapOair deal was found by Cheapflights users on 1/12. 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.
Sat 2/219:25 pm
RDU
-
SJU
1 stop28h 28m
Frontier
Mon 2/233:53 am
SJU
-
RDU
1 stop14h 06m
Frontier
Deal found 1/12$155
This Booking.com deal was found by Cheapflights users on 1/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/74:19 pm
RDU
-
SJU
1 stop23h 38m
Frontier
Wed 2/114:06 pm
SJU
-
RDU
1 stop9h 00m
Frontier
Deal found 1/11$160
This Frontier deal was found by Cheapflights users on 1/11. 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 1/187:19 pm
RDU
-
SJU
Nonstop3h 21m
Frontier
Sat 1/246:11 pm
SJU
-
RDU
1 stop6h 45m
Frontier
Deal found 1/11$161
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 2/810:53 am
RDU
-
SJU
1 stop7h 05m
Multiple Airlines
Thu 2/196:00 am
SJU
-
RDU
Nonstop3h 53m
Multiple Airlines
Deal found 1/11$164
This Expedia deal was found by Cheapflights users on 1/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/32:53 pm
RDU
-
SJU
1 stop11h 00m
Frontier
Mon 3/161:59 am
SJU
-
RDU
1 stop8h 06m
Frontier
Deal found 1/12$165
This CheapOair deal was found by Cheapflights users on 1/10. 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.
Wed 3/42:53 pm
RDU
-
SJU
1 stop11h 00m
Frontier
Fri 3/131:59 am
SJU
-
RDU
1 stop20h 55m
Frontier
Deal found 1/10$166
This Kiwi.com deal was found by Cheapflights users on 1/12. 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 2/245:54 pm
RDU
-
SJU
1 stop5h 49m
Frontier
Tue 3/35:25 pm
SJU
-
RDU
1 stop21h 33m
Frontier
Deal found 1/12$167
This Kiwi.com deal was found by Cheapflights users on 1/11. 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 4/19:58 pm
IAD
-
SJU
1 stop17h 01m
Frontier
Tue 4/76:00 am
SJU
-
IAD
1 stop15h 13m
Frontier
Deal found 1/11$181
This Frontier deal was found by Cheapflights users on 1/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/21:31 pm
IAD
-
SJU
1 stop9h 28m
Frontier
Wed 2/113:53 am
SJU
-
IAD
1 stop6h 32m
Frontier
Deal found 1/9$182
This CheapOair deal was found by Cheapflights users on 1/11. 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.
Thu 2/268:07 pm
IAD
-
SJU
1 stop29h 18m
Frontier
Wed 3/45:25 pm
SJU
-
IAD
1 stop17h 00m
Frontier
Deal found 1/11$183

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 January 12, 2026.
Use the filters below to find and compare flights from Virginia to Caribbean that are best for you.

Fly from

Virginia

Fly to

Caribbean

Route

Depart

Return

Price

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 2/22

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 2/26

5:50 pm-8:55 pm

Nonstop4h 05m

$243

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 3/4

3:59 pm-12:59 am

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Sat 3/7

6:59 pm-9:59 pm

Nonstop4h 00m

$248

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 4/10

8:00 am-11:45 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 4/14

11:25 pm-7:59 am

1 stop8h 34m

$248

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 4/10

3:59 pm-12:51 am

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sun 4/12

6:05 pm-9:59 pm

Nonstop3h 54m

$248

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 1/27

6:00 am-4:50 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:00 am-4:29 pm

1 stop10h 29m

$252

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 2/23

1:40 pm-11:58 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Thu 2/26

6:15 am-12:40 pm

1 stop7h 25m

$252

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 2/25

3:59 pm-12:59 am

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:05 am-2:43 pm

1 stop9h 38m

$253

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sun 3/1

8:59 am-1:56 pm

Nonstop3h 57m

Saint Thomas Island Cyril E King

Thu 3/5

1:02 pm-4:25 pm

Nonstop4h 23m

$271

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 1/23

6:00 am-5:17 pm

1 stop10h 17m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:27 pm-12:24 am

1 stop6h 57m

$272

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 2/18

10:08 am-9:12 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:37 pm-12:21 am

1 stop6h 44m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/12

Showing 1-10 of 60 results
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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, May is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $113). Flying from Virginia to Caribbean in June is currently the most expensive (average of $210). 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.

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 50m. United Airlines provides one of the quickest options available for as low as $243. Virginia and Caribbean are separated by a distance of 1573 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), Delta ($73), and Frontier ($84).

  • 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, May is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $113). Flying from Virginia to Caribbean in June is currently the most expensive (average of $210). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$90Average$397FlexibilityNo cancel feeOn-time65%
FrontierCheapest$90Average$283FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$183Average$493FlexibilityNo cancel feeOn-time62%
DeltaCheapest$205Average$553FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$599FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$619FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$250Average$644FlexibilityNo cancel feeOn-time63%

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