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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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jan 29 — Feb 51
Thu 1/29
Thu 2/5
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 December 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:15 pmIAD - SJU
Nonstop3h 54mFrontier
Fri 1/93:11 pmSJU - IAD
Nonstop4h 13mFrontier
Deal found 12/29$179
This Cheapflightsfares deal was found by Cheapflights users on 12/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:15 pmIAD - SJU
Nonstop3h 54mFrontier
Fri 1/163:11 pmSJU - IAD
Nonstop4h 08mFrontier
Deal found 12/28$195
This Frontier deal was found by Cheapflights users on 12/29. 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 12/308:15 pmIAD - SJU
Nonstop3h 54mFrontier
Sat 1/102:57 pmSJU - IAD
Nonstop4h 13mFrontier
Deal found 12/29$212
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 pmRDU - SJU
1 stop23h 59mMultiple Airlines
Thu 1/85:45 amSJU - RDU
1 stop10h 05mMultiple Airlines
Deal found 12/28$222
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 pmRDU - SJU
1 stop13h 25mFrontier
Thu 1/85:45 amSJU - RDU
1 stop10h 05mFrontier
Deal found 12/28$223
This Frontier deal was found by Cheapflights users on 12/29. 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 12/308:15 pmIAD - SJU
Nonstop3h 54mFrontier
Thu 1/86:30 amSJU - IAD
1 stop8h 56mFrontier
Deal found 12/29$226
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:42 pmRDU - SJU
Nonstop3h 33mFrontier
Wed 1/79:19 pmSJU - RDU
1 stop12h 58mFrontier
Deal found 12/28$250
This Frontier deal was found by Cheapflights users on 12/28. 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.
Mon 12/296:42 pmRDU - SJU
Nonstop3h 33mFrontier
Wed 1/72:29 amSJU - RDU
1 stop6h 47mFrontier
Deal found 12/28$253
This Kiwi.com deal was found by Cheapflights users on 12/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:14 pmRDU - SJU
1 stop7h 25mFrontier
Wed 1/79:19 pmSJU - RDU
1 stop12h 58mFrontier
Deal found 12/28$262
This Kiwi.com deal was found by Cheapflights users on 12/29. 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 12/306:14 pmRDU - SJU
1 stop23h 59mMultiple Airlines
Wed 1/79:19 pmSJU - RDU
1 stop12h 58mMultiple Airlines
Deal found 12/29$277
This American Airlines deal was found by Cheapflights users on 12/27. 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 12/319:42 amDCA - SJU
1 stop12h 52mAmerican Airlines
Sat 1/106:30 amSJU - DCA
1 stop11h 20mAmerican Airlines
Deal found 12/27$348
This JetBlue deal was found by Cheapflights users on 12/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:00 amDCA - SJU
Nonstop3h 40mJetBlue
Tue 1/68:00 amSJU - DCA
1 stop9h 19mJetBlue
Deal found 12/29$355

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 December 30, 2025.

Round-trip from

$158
(Kiwi.com)

One-way from

$77
(Frontier)

Popular in

December

Cheapest in

September

Average price

$567

Good round-trip deal

$244 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 December 2025
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 December 30, 2025.
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

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 2/2

12:00 pm-12:36 am

2 stops11h 36m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:05 am-8:32 am

1 stop7h 27m

$207

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 2/22

11:00 am-9:26 pm

1 stop9h 26m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:40 am-3:55 pm

1 stop9h 15m

$207

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 2/7

4:15 pm-6:11 am

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Fri 2/13

2:05 am-8:29 am

1 stop7h 24m

$207

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 1/19

3:15 pm-12:36 am

1 stop8h 21m

San Juan Luis Munoz Marin Intl

Thu 1/22

4:52 pm-11:59 pm

1 stop8h 07m

$207

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 2/3

6:00 am-5:17 pm

1 stop10h 17m

San Juan Luis Munoz Marin Intl

Sat 2/7

1:07 pm-8:20 pm

1 stop8h 13m

$216

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 1/20

6:00 am-4:10 pm

1 stop9h 10m

Saint Thomas Island Cyril E King

Thu 1/22

1:52 pm-8:45 pm

1 stop7h 53m

$219

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 1/28

6:03 am-4:36 pm

1 stop9h 33m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:45 pm-9:13 pm

1 stop7h 28m

$221

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 2/8

8:15 am-1:06 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Thu 2/12

6:10 am-12:59 pm

1 stop7h 49m

$225

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 2/24

12:00 pm-9:00 pm

1 stop8h 00m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:05 am-9:29 am

1 stop8h 24m

$227

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 1/5

12:59 pm-8:09 pm

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Wed 1/14

7:45 am-7:32 pm

2 stops12h 47m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

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 $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 51m. United Airlines provides one of the quickest options available for as low as $225. 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), 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 $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 December 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$90Average$398FlexibilityNo cancel feeOn-time65%
FrontierCheapest$90Average$276FlexibilityNo cancel feeOn-time62%
DeltaCheapest$205Average$514FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$586FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$612FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$244Average$547FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$252Average$635FlexibilityNo cancel feeOn-time63%

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