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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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/246:55 amIAD - SJU
2 stops12h 32mMultiple Airlines
Tue 11/254:08 pmSJU - IAD
Nonstop4h 03mMultiple Airlines
Deal found 11/6$187
This Super.com deal was found by Cheapflights users on 11/6. 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.
Thu 12/1110:38 amIAD - SJU
Nonstop3h 54mFrontier
Sun 12/146:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/6$189
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/198:40 amIAD - SJU
1 stop15h 26mFrontier
Sat 11/223:58 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 11/6$190
This Super.com deal was found by Cheapflights users on 11/5. 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 12/710:38 amIAD - SJU
Nonstop3h 54mFrontier
Thu 12/116:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/5$199
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1812:39 pmDCA - SJU
1 stop9h 34mDelta
Thu 11/203:20 pmSJU - DCA
1 stop8h 44mDelta
Deal found 11/4$200
This Kiwi.com deal was found by Cheapflights users on 11/6. 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
Tue 11/259:30 pmSJU - IAD
1 stop15h 22mFrontier
Deal found 11/6$201
This Super.com deal was found by Cheapflights users on 11/5. 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 12/710:38 amIAD - SJU
Nonstop3h 54mFrontier
Sun 12/146:30 amSJU - IAD
Nonstop4h 13mFrontier
Deal found 11/5$203
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/164:04 pmIAD - SJU
1 stop8h 28mFrontier
Sat 11/223:58 pmSJU - IAD
Nonstop4h 03mFrontier
Deal found 11/6$204
This Trip.com deal was found by Cheapflights users on 11/5. 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.
Mon 11/178:00 amDCA - SJU
Nonstop3h 50mJetBlue
Thu 11/206:10 pmSJU - DCA
Nonstop3h 58mJetBlue
Deal found 11/5$204
This Super.com deal was found by Cheapflights users on 11/6. 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.
Fri 11/288:06 pmIAD - SJU
Nonstop3h 47mFrontier
Sat 12/64:31 pmSJU - IAD
1 stop7h 34mFrontier
Deal found 11/6$208
This CheapOair deal was found by Cheapflights users on 11/5. 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 11/297:56 pmIAD - SJU
Nonstop3h 47mFrontier
Fri 12/53:55 amSJU - IAD
1 stop17h 29mFrontier
Deal found 11/5$210
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/167:26 pmIAD - SJU
Nonstop3h 52mMultiple Airlines
Sat 11/2211:55 amSJU - IAD
2 stops13h 04mMultiple Airlines
Deal found 11/6$211

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 November 6, 2025.

Round-trip from

$187
(Kiwi.com)

One-way from

$83
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$400
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 ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 6, 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

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Mon 1/19

7:15 am-2:30 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-11:44 am

1 stop6h 29m

$225

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Thu 12/11

5:32 pm-10:22 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 12/18

5:50 pm-8:55 pm

Nonstop4h 05m

$226

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sun 11/16

8:00 am-12:50 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 11/19

6:51 pm-9:48 pm

Nonstop3h 57m

$256

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 11/13

7:30 am-5:05 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Thu 11/20

8:55 am-5:25 pm

2 stops9h 30m

$265

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 1/1

7:20 am-6:15 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Tue 1/13

6:45 pm-9:46 pm

Nonstop4h 01m

$278

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Tue 1/20

11:20 am-3:47 pm

Nonstop3h 27m

San Juan Luis Munoz Marin Intl

Fri 2/13

7:56 am-10:40 am

Nonstop3h 44m

$282

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 12/12

8:00 am-12:51 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Mon 12/15

6:40 pm-9:37 pm

Nonstop3h 57m

$290

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Mon 12/22

8:00 am-12:40 pm

Nonstop3h 40m

San Juan Luis Munoz Marin Intl

Wed 12/24

6:47 pm-9:44 pm

Nonstop3h 57m

$290

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 11/13

7:30 am-5:05 pm

1 stop8h 35m

San Juan Luis Munoz Marin Intl

Tue 11/18

3:55 pm-10:50 pm

1 stop7h 55m

$292

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Mon 12/8

2:20 pm-6:43 pm

Nonstop3h 23m

San Juan Luis Munoz Marin Intl

Tue 12/16

4:55 pm-10:17 pm

1 stop6h 22m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 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 November 6, 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 50m. Delta provides one of the quickest options available for as low as $226. 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 Frontier ($83), Delta ($93), and United Airlines ($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 $113). 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

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$310FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$438FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$208Average$598FlexibilityNo cancel feeOn-time69%
DeltaCheapest$231Average$528FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$570FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$240Average$609FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$641FlexibilityNo cancel feeOn-time63%

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