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$76+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
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 February 11, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Fri 2/208:20 pm
IAD
-
SJU
Nonstop3h 45m
Multiple Airlines
Fri 2/276:27 pm
SJU
-
IAD
1 stop16h 07m
Multiple Airlines
Deal found 2/9$165
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1112:28 pm
IAD
-
SJU
Nonstop3h 53m
Frontier
Wed 4/156:30 am
SJU
-
IAD
1 stop24h 57m
Frontier
Deal found 2/10$168
This Travelocity deal was found by Cheapflights users on 2/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Sat 2/283:53 am
SJU
-
IAD
1 stop28h 27m
Frontier
Deal found 2/10$169
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 2/218:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Wed 2/253:53 am
SJU
-
IAD
1 stop6h 32m
Frontier
Deal found 2/9$171
This Gotogate deal was found by Cheapflights users on 2/9. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Fri 2/276:00 am
SJU
-
IAD
1 stop13h 07m
Frontier
Deal found 2/9$174
This Trip.com deal was found by Cheapflights users on 2/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/148:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Fri 2/204:17 pm
SJU
-
IAD
Nonstop4h 08m
Frontier
Deal found 2/9$175
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Sat 2/283:53 am
SJU
-
IAD
1 stop28h 27m
Frontier
Deal found 2/10$176
This Frontier deal was found by Cheapflights users on 2/9. 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.
Fri 2/208:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Wed 2/253:53 am
SJU
-
IAD
1 stop6h 32m
Frontier
Deal found 2/9$178
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Tue 2/246:25 am
RDU
-
SJU
2 stops11h 33m
Multiple Airlines
Mon 3/23:53 am
SJU
-
RDU
1 stop11h 05m
Multiple Airlines
Deal found 2/9$180
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:05 pm
IAD
-
SJU
2 stops18h 17m
Multiple Airlines
Fri 2/274:17 pm
SJU
-
IAD
Nonstop4h 08m
Multiple Airlines
Deal found 2/10$181
This Kiwi.com deal was found by Cheapflights users on 2/9. 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.
Mon 5/119:11 pm
RDU
-
SJU
Nonstop3h 29m
Frontier
Sat 5/163:08 am
SJU
-
RDU
1 stop6h 51m
Frontier
Deal found 2/9$181
This Flightnetwork deal was found by Cheapflights users on 2/9. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/229:38 am
RDU
-
SJU
Nonstop3h 21m
Frontier
Sat 2/282:54 am
SJU
-
RDU
1 stop20h 10m
Frontier
Deal found 2/9$182

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 February 11, 2026.

Round-trip from

$165
(Kiwi.com)

One-way from

$76
(Super.com)

Popular in

December

Cheapest in

September

Average price

$374

Good round-trip deal

$272 or less
From Virginia to Caribbean
Search Deals
One-way flight from Virginia to Caribbean
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($45 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 February 2026
Search Deals
Price to beat on a round-trip 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 February 11, 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.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Wed 3/18

7:30 am-3:18 pm

1 stop7h 48m

Saint Thomas Island Cyril E King

Tue 3/24

2:05 pm-11:59 pm

1 stop9h 54m

$200

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Mon 3/16

6:30 am-3:18 pm

1 stop8h 48m

Saint Thomas Island Cyril E King

Thu 3/19

2:35 pm-11:50 pm

1 stop9h 15m

$200

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 4/7

8:15 am-12:20 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 4/15

2:10 pm-12:15 am

1 stop10h 05m

$206

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Mon 3/16

7:30 am-3:18 pm

1 stop7h 48m

Saint Thomas Island Cyril E King

Wed 3/25

2:05 pm-10:52 pm

1 stop8h 47m

$210

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Wed 2/25

11:45 am-4:12 pm

Nonstop3h 27m

San Juan Luis Munoz Marin Intl

Tue 3/3

3:53 am-4:59 pm

1 stop14h 06m

$217

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Thu 3/5

6:05 am-1:22 pm

1 stop6h 17m

Saint Thomas Island Cyril E King

Mon 3/9

3:00 pm-10:42 pm

1 stop7h 42m

$220

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Sun 5/10

6:00 am-3:21 pm

1 stop9h 21m

Saint Thomas Island Cyril E King

Fri 5/15

4:20 pm-11:24 pm

1 stop7h 04m

$220

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Tue 4/28

6:00 am-12:12 pm

1 stop6h 12m

Saint Thomas Island Cyril E King

Thu 5/7

4:20 pm-11:24 pm

1 stop7h 04m

$220

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Mon 5/11

6:00 am-3:21 pm

1 stop9h 21m

Saint Thomas Island Cyril E King

Fri 5/15

4:20 pm-11:24 pm

1 stop7h 04m

$220

Washington, D.C.Saint Thomas Island

DCA - STT

DCASTT

Washington, D.C. Reagan-National

Wed 3/4

7:30 am-4:22 pm

1 stop7h 52m

Saint Thomas Island Cyril E King

Tue 3/10

12:49 pm-9:41 pm

1 stop8h 52m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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, February is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $118). Flying from Virginia to Caribbean in November is currently the most expensive (average of $208). 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 27m. United Airlines provides one of the quickest options available for as low as $237. 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), Delta ($73), and Frontier ($77).

  • 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 $118). Flying from Virginia to Caribbean in November is currently the most expensive (average of $208). 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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$90Average$405FlexibilityNo cancel feeOn-time65%
FrontierCheapest$110Average$286FlexibilityNo cancel feeOn-time62%
DeltaCheapest$146Average$530FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$204Average$524FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$205Average$648FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$225Average$593FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$603FlexibilityNo cancel feeOn-time71%

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