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$90+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$168

One-way from

$90
(Frontier)

Popular in

December

Cheapest in

September

Average price

$301
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. 5% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This deal was found by Cheapflights users on 9/15. 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.
Sun 11/167:26 pmIAD - SJU
Nonstop3h 52mFrontier
Fri 11/214:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 9/15$168
This Kiwi.com deal was found by Cheapflights users on 9/17. 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.
Thu 10/239:07 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 10/307:30 amSJU - IAD
1 stop13h 27mFrontier
Deal found 9/17$176
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/27:26 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 11/93:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/15$181
This Frontier deal was found by Cheapflights users on 9/15. 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 10/199:07 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 11/23:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/15$183
This Frontier deal was found by Cheapflights users on 9/15. 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.
Thu 10/308:26 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 11/63:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/15$184
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Sun 10/269:07 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 11/23:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/16$187
This CheapOair deal was found by Cheapflights users on 9/15. 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 10/239:07 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 10/264:26 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/15$189
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/169:07 pmIAD - SJU
Nonstop3h 52mFrontier
Sun 10/194:26 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/16$191
This Frontier deal was found by Cheapflights users on 9/16. 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.
Thu 12/1110:08 amIAD - SJU
Nonstop3h 54mFrontier
Wed 12/173:59 pmSJU - IAD
1 stop7h 20mFrontier
Deal found 9/16$192
This Frontier deal was found by Cheapflights users on 9/15. 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 10/56:10 amIAD - SJU
1 stop8h 01mFrontier
Thu 10/94:26 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 9/15$197
This Frontier deal was found by Cheapflights users on 9/16. 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 10/269:07 pmIAD - SJU
Nonstop3h 52mFrontier
Wed 10/295:51 pmSJU - IAD
2 stops22h 43mFrontier
Deal found 9/16$201
This Trip.com deal was found by Cheapflights users on 9/15. 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.
Wed 10/158:30 amDCA - SJU
Nonstop3h 45mJetBlue
Fri 10/176:05 pmSJU - DCA
Nonstop3h 52mJetBlue
Deal found 9/15$219

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 September 17, 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 10/20

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 11/5

6:57 pm-9:54 pm

Nonstop3h 57m

$236

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 10/21

7:37 am-1:52 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Fri 10/24

6:05 pm-9:57 pm

Nonstop3h 52m

$246

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sat 10/4

7:45 am-4:31 pm

1 stop8h 46m

San Juan Luis Munoz Marin Intl

Sat 10/11

7:15 am-2:54 pm

1 stop7h 39m

$261

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Wed 10/1

7:50 am-4:31 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Sat 10/4

7:30 am-2:03 pm

1 stop6h 33m

$261

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 11/10

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 11/13

5:50 pm-8:55 pm

Nonstop4h 05m

$266

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 10/22

8:30 am-12:15 pm

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 11/3

6:51 pm-9:48 pm

Nonstop3h 57m

$266

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 12/9

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Mon 12/15

6:51 pm-9:48 pm

Nonstop3h 57m

$266

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 12/2

1:45 pm-11:54 pm

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:51 pm-9:48 pm

Nonstop3h 57m

$268

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 12/5

3:40 pm-11:54 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:51 pm-9:48 pm

Nonstop3h 57m

$268

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Fri 11/14

12:35 pm-10:04 pm

1 stop8h 29m

San Juan Luis Munoz Marin Intl

Wed 11/19

5:05 am-11:47 am

1 stop7h 42m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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, September is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $254). Flying from Virginia to Caribbean in June is currently the most expensive (average of $339). 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 September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Virginia to Caribbean as you normally would.

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 45m. JetBlue provides one of the quickest options available for as low as $236. 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 Frontier ($113), United Airlines ($118), and JetBlue ($118).

  • 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, September is the cheapest month in which you can book a flight from Virginia to Caribbean (average of $254). Flying from Virginia to Caribbean in June is currently the most expensive (average of $339). 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 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$428FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$560FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$594FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$534FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$630FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$647FlexibilityNo cancel feeOn-time63%

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