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$83+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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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 October 23, 2025.

This Frontier deal was found by Cheapflights users on 10/20. 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 11/36:00 amIAD - SJU
1 stop8h 19mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/20$184
This Frontier deal was found by Cheapflights users on 10/20. 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 11/242:11 pmIAD - SJU
1 stop7h 58mFrontier
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 10/20$187
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/710:38 amIAD - SJU
Nonstop3h 54mFrontier
Thu 12/1110:42 amSJU - IAD
1 stop29h 23mFrontier
Deal found 10/21$189
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/238:06 pmIAD - SJU
Nonstop3h 47mFrontier
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 10/20$191
This Frontier deal was found by Cheapflights users on 10/22. 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 11/24:04 pmIAD - SJU
1 stop8h 28mFrontier
Thu 11/63:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/22$192
This Frontier deal was found by Cheapflights users on 10/23. 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 12/18:06 pmIAD - SJU
Nonstop3h 47mFrontier
Thu 12/46:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 10/23$195
This Frontier deal was found by Cheapflights users on 10/21. 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 11/67:26 pmIAD - SJU
Nonstop3h 52mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/21$197
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/85:58 amIAD - SJU
2 stops25h 47mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/21$198
This Trip.com deal was found by Cheapflights users on 10/22. 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.
Tue 11/118:00 amDCA - SJU
Nonstop3h 50mJetBlue
Sat 12/66:51 pmSJU - DCA
Nonstop3h 57mJetBlue
Deal found 10/22$200
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/118:40 amIAD - SJU
2 stops41h 53mFrontier
Thu 11/133:45 pmSJU - IAD
Nonstop3h 56mFrontier
Deal found 10/21$201
This Frontier deal was found by Cheapflights users on 10/23. 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 11/176:00 amIAD - SJU
1 stop8h 19mFrontier
Mon 11/244:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 10/23$203
This Frontier deal was found by Cheapflights users on 10/21. 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 11/134:00 pmIAD - SJU
1 stop8h 32mFrontier
Sun 11/234:08 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 10/21$204

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 October 23, 2025.

Round-trip from

$184
(Frontier)

One-way from

$83
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$361
From Virginia to Caribbean
Search Deals
One-way flight from Virginia to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 23, 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

Sat 11/1

8:00 am-11:51 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Wed 11/5

5:05 am-12:27 pm

1 stop8h 22m

$224

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Tue 11/11

12:11 pm-11:56 pm

1 stop10h 45m

San Juan Luis Munoz Marin Intl

Sat 12/6

7:00 am-2:40 pm

1 stop8h 40m

$247

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sun 12/7

2:20 pm-6:43 pm

Nonstop3h 23m

San Juan Luis Munoz Marin Intl

Mon 12/8

10:45 am-1:25 pm

Nonstop3h 40m

$258

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sun 12/7

2:20 pm-6:43 pm

Nonstop3h 23m

San Juan Luis Munoz Marin Intl

Wed 12/10

10:45 am-1:25 pm

Nonstop3h 40m

$258

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sun 12/7

2:20 pm-6:43 pm

Nonstop3h 23m

San Juan Luis Munoz Marin Intl

Tue 12/9

10:45 am-1:25 pm

Nonstop3h 40m

$258

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Fri 12/5

2:20 pm-6:43 pm

Nonstop3h 23m

San Juan Luis Munoz Marin Intl

Tue 12/9

10:45 am-1:25 pm

Nonstop3h 40m

$258

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Wed 11/19

4:55 pm-3:48 am

1 stop9h 53m

San Juan Luis Munoz Marin Intl

Mon 11/24

6:10 pm-9:08 pm

Nonstop3h 58m

$291

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 11/2

7:05 am-5:33 pm

1 stop9h 28m

San Juan Luis Munoz Marin Intl

Tue 11/11

3:32 pm-9:32 pm

1 stop7h 00m

$295

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 12/7

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Wed 12/10

6:51 pm-9:48 pm

Nonstop3h 57m

$295

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 11/3

8:00 am-12:50 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 11/6

6:57 pm-9:54 pm

Nonstop3h 57m

$296

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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 $109). Flying from Virginia to Caribbean in February is currently the most expensive (average of $230). 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 October 23, 2025.

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 in the evening, which can drop the price by up to 23% versus a flight in the morning.

What is the cheapest day to fly from Virginia to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Virginia to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Virginia to Caribbean flight should consider departing on Tuesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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. JetBlue provides one of the quickest options available for as low as $224. 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 Delta ($93), United Airlines ($108), and JetBlue ($108).

  • 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 $109). Flying from Virginia to Caribbean in February is currently the most expensive (average of $230). 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$436FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$576FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$589FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$546FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$244Average$614FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$615FlexibilityNo cancel feeOn-time63%

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