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Caribbean Islands

$123+ Cheap flights from Virginia to Caribbean Islands

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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jul 10 — Jul 171
Fri 7/10
Fri 7/17
1 adult, Economy
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Cheap flight deals from Virginia to Caribbean Islands

Cheapest flights from Virginia to Caribbean Islands
Explore the most affordable flight options available from Virginia to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 10, 2026.

This Frontier deal was found by Cheapflights users on 6/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:56 pm
RDU
-
SJU
Nonstop3h 38m
Frontier
Thu 9/38:00 am
SJU
-
RDU
Nonstop3h 43m
Frontier
Deal found 6/5$261
This Super.com deal was found by Cheapflights users on 6/5. 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 8/28:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Sun 8/93:36 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 6/5$263
This Frontier deal was found by Cheapflights users on 6/7. 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 7/308:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Tue 8/113:36 pm
SJU
-
RDU
Nonstop3h 52m
Frontier
Deal found 6/7$264
This Frontier deal was found by Cheapflights users on 6/7. 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 7/288:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Tue 8/46:00 am
SJU
-
RDU
1 stop11h 09m
Frontier
Deal found 6/7$265
This Kiwi.com deal was found by Cheapflights users on 6/6. 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 8/2312:56 pm
RDU
-
SJU
Nonstop3h 38m
Frontier
Wed 8/266:41 pm
SJU
-
RDU
1 stop12h 40m
Frontier
Deal found 6/6$267
This Super.com deal was found by Cheapflights users on 6/5. 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 8/2312:56 pm
RDU
-
SJU
Nonstop3h 38m
Frontier
Thu 9/38:00 am
SJU
-
RDU
Nonstop3h 43m
Frontier
Deal found 6/5$268
This Kiwi.com deal was found by Cheapflights users on 6/9. 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 8/118:56 am
RDU
-
SJU
1 stop7h 15m
Frontier
Thu 8/206:00 am
SJU
-
RDU
1 stop8h 04m
Frontier
Deal found 6/9$271
This Frontier deal was found by Cheapflights users on 6/9. 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.
Tue 8/48:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Tue 8/116:00 am
SJU
-
RDU
1 stop11h 15m
Frontier
Deal found 6/9$272
This Flightnetwork deal was found by Cheapflights users on 6/10. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:23 pm
RDU
-
SJU
Nonstop3h 44m
Frontier
Tue 7/143:00 pm
SJU
-
RDU
1 stop17h 48m
Frontier
Deal found 6/10$273
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:09 pm
IAD
-
SJU
1 stop22h 02m
Frontier
Fri 8/216:00 am
SJU
-
IAD
1 stop13h 52m
Frontier
Deal found 6/5$274
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:28 pm
IAD
-
SJU
1 stop12h 13m
Frontier
Fri 8/216:00 am
SJU
-
IAD
1 stop13h 52m
Frontier
Deal found 6/5$275
This Frontier deal was found by Cheapflights users on 6/7. 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 8/1812:56 pm
RDU
-
SJU
Nonstop3h 38m
Frontier
Tue 8/183:06 am
SJU
-
RDU
1 stop6h 13m
Frontier
Deal found 6/7$275

Find flight deals from Virginia to Caribbean Islands

Keep the following information in mind while searching for Virginia to Caribbean Islands flight deals. Data was last updated June 10, 2026.

Round-trip from

$261
(Frontier)

One-way from

$123
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$414
From Virginia to Caribbean Islands
Search Deals
One-way flight from Virginia to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Virginia to Caribbean Islands 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 June 10, 2026.
Use the filters below to find and compare flights from Virginia to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 8/29

11:55 am-7:20 pm

1 stop7h 25m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:45 pm-11:55 pm

1 stop6h 10m

$286

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sat 8/22

8:28 am-3:02 pm

1 stop6h 34m

Saint Thomas Island Cyril E King

Mon 8/31

2:49 pm-12:34 am

1 stop9h 45m

$342

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 8/18

6:10 am-4:25 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Sat 8/22

6:25 am-3:55 pm

1 stop9h 30m

$351

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Thu 9/3

12:55 pm-8:05 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Mon 9/7

5:45 pm-11:55 pm

1 stop6h 10m

$361

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Mon 8/24

7:56 pm-11:34 pm

Nonstop3h 38m

San Juan Luis Munoz Marin Intl

Wed 8/26

6:50 am-1:04 pm

1 stop6h 14m

$367

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 8/26

9:00 am-12:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Tue 9/1

3:56 pm-12:44 am

1 stop8h 48m

$376

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Wed 9/2

6:15 am-1:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Sun 9/6

4:55 pm-8:47 pm

Nonstop3h 52m

$376

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Sat 8/29

8:20 am-12:19 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Wed 9/2

3:01 pm-9:16 pm

1 stop6h 15m

$376

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sun 8/16

1:55 pm-12:30 am

2 stops10h 35m

San Juan Luis Munoz Marin Intl

Fri 8/21

6:30 am-4:10 pm

2 stops9h 40m

$389

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Fri 9/4

2:50 pm-11:05 pm

1 stop8h 15m

San Juan Luis Munoz Marin Intl

Mon 9/7

6:30 am-2:40 pm

2 stops8h 10m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/6

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Virginia to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Virginia to Caribbean Islands?

Currently, October is the cheapest month in which you can book a flight from Virginia to Caribbean Islands (average of $116). Flying from Virginia to Caribbean Islands in August is currently the most expensive (average of $1,054). 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 EPX?

Find hourly flight availability from Virginia to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 10, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 30% on flights from Virginia to Caribbean Islands by exploring options for tickets at noon.

How far ahead should I book a flight from Virginia to Caribbean Islands?

To ensure you get the cheapest price possible for a flight from Virginia to Caribbean Islands, you should look to book at least 52 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Related info for your journey

Find useful and relevant information for your journey from Virginia to Caribbean Islands. 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 Islands?

    Airlines like Southwest, Delta, and JetBlue fly from Virginia to Caribbean Islands in about 3h 38m. The time it takes to get you to your destination can typically vary by up to 3h 47m. Airlines will cover a distance of 1435 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Virginia to Caribbean Islands one-way?

    To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $84. Delta flights start at $94 while deals on American Airlines start at $98 one-way.

  • Can I find deals for flights from Virginia to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Virginia to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Virginia to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Virginia to Caribbean Islands.

  • Can I find deals for business class flights from Virginia to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Virginia to Caribbean Islands 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 Islands?

    Currently, October is the cheapest month in which you can book a flight from Virginia to Caribbean Islands (average of $116). Flying from Virginia to Caribbean Islands in August is currently the most expensive (average of $1,054). 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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Alternative routes for Virginia to Caribbean Islands

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Top 7 airlines flying from Virginia to Caribbean Islands

Discover the top 7 airlines that operate flights from Virginia to Caribbean Islands. 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 June 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$96Average$300FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$107Average$501FlexibilityNo cancel feeOn-time62%
DeltaCheapest$112Average$507FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$205Average$595FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$212Average$602FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$533FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$646Average$646FlexibilityNo cancel feeOn-time75%

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