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Caribbean Islands

$75+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This Super.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/148:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Sat 2/214:17 pm
SJU
-
IAD
Nonstop4h 08m
Frontier
Deal found 2/2$166
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/148:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Fri 2/204:17 pm
SJU
-
IAD
Nonstop4h 08m
Frontier
Deal found 2/2$168
This Super.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/288:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Mon 3/95:30 am
SJU
-
IAD
1 stop8h 14m
Frontier
Deal found 2/2$169
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/91:31 pm
IAD
-
SJU
1 stop22h 26m
Frontier
Sat 2/144:17 pm
SJU
-
IAD
Nonstop4h 08m
Frontier
Deal found 2/1$172
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Mon 3/28:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Wed 3/1112:15 pm
SJU
-
IAD
1 stop25h 29m
Frontier
Deal found 2/2$174
This Frontier deal was found by Cheapflights users on 2/3. 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 3/28:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Mon 3/95:30 am
SJU
-
IAD
1 stop8h 14m
Frontier
Deal found 2/3$177
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/148:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Sun 2/226:00 am
SJU
-
IAD
1 stop27h 09m
Frontier
Deal found 2/3$178
This Frontier deal was found by Cheapflights users on 2/2. 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 3/28:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Thu 3/125:30 am
SJU
-
IAD
1 stop8h 14m
Frontier
Deal found 2/2$179
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/208:20 pm
IAD
-
SJU
Nonstop3h 45m
Frontier
Wed 2/253:53 am
SJU
-
IAD
1 stop6h 32m
Frontier
Deal found 2/1$180
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 2/91:31 pm
IAD
-
SJU
1 stop22h 26m
Frontier
Fri 2/134:17 pm
SJU
-
IAD
Nonstop4h 08m
Frontier
Deal found 2/1$181
This CheapOair deal was found by Cheapflights users on 2/3. 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 4/1112:28 pm
IAD
-
SJU
Nonstop3h 53m
Frontier
Wed 4/156:30 am
SJU
-
IAD
1 stop24h 57m
Frontier
Deal found 2/3$182
This Frontier deal was found by Cheapflights users on 2/1. 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.
Sat 3/219:07 pm
RDU
-
SJU
Nonstop3h 21m
Frontier
Sat 3/284:19 pm
SJU
-
RDU
Nonstop3h 53m
Frontier
Deal found 2/1$183

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 February 3, 2026.

Round-trip from

$166
(Super.com)

One-way from

$75
(eDestinos)

Popular in

December

Cheapest in

September

Average price

$372
From Virginia to Caribbean Islands
Search Deals
One-way flight from Virginia to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($49 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 February 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 February 3, 2026.
Use the filters below to find and compare flights from Virginia to Caribbean Islands that are best for you.

Fly from

Virginia

Fly to

Caribbean Islands

Route

Depart

Return

Price

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sun 3/22

8:59 am-12:56 pm

Nonstop3h 57m

Saint Thomas Island Cyril E King

Thu 3/26

2:35 pm-11:51 pm

1 stop9h 16m

$196

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 2/23

8:59 am-1:56 pm

Nonstop3h 57m

Saint Thomas Island Cyril E King

Wed 2/25

5:25 pm-11:21 pm

1 stop6h 56m

$196

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sun 3/8

8:59 am-12:56 pm

Nonstop3h 57m

Saint Thomas Island Cyril E King

Tue 3/17

4:25 pm-11:19 pm

1 stop6h 54m

$217

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 2/23

7:15 am-3:04 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Fri 2/27

3:10 pm-12:21 am

1 stop10h 11m

$220

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 2/24

7:15 am-3:04 pm

1 stop6h 49m

Saint Thomas Island Cyril E King

Fri 2/27

3:10 pm-12:21 am

1 stop10h 11m

$220

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Tue 4/14

8:15 am-12:20 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Tue 4/21

4:45 pm-8:58 pm

Nonstop4h 13m

$223

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sat 5/2

8:20 am-5:00 pm

1 stop8h 40m

Saint Thomas Island Cyril E King

Tue 5/5

4:45 pm-8:58 pm

Nonstop4h 13m

$228

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Sat 2/21

6:00 am-4:22 pm

1 stop9h 22m

Saint Thomas Island Cyril E King

Thu 2/26

3:10 pm-12:21 am

1 stop10h 11m

$231

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Sat 2/21

11:40 am-4:07 pm

Nonstop3h 27m

San Juan Luis Munoz Marin Intl

Sun 2/22

8:00 am-10:44 am

Nonstop3h 44m

$237

RaleighSan Juan

RDU - SJU

RDUSJU

Raleigh-Durham

Tue 3/3

11:45 am-4:12 pm

Nonstop3h 27m

San Juan Luis Munoz Marin Intl

Sun 3/8

7:35 am-11:20 am

Nonstop3h 45m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 60 results
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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, May is the cheapest month in which you can book a flight from Virginia to Caribbean Islands (average of $113). Flying from Virginia to Caribbean Islands in June is currently the most expensive (average of $214). 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 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 United Airlines, Delta, and JetBlue fly from Virginia to Caribbean Islands in about 3h 27m. The time it takes to get you to your destination can typically vary by up to 3h 22m. 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 Spirit Airlines, which is currently one of the cheapest options available, starting at $69. Delta flights start at $73 while deals on Frontier start at $85 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, May is the cheapest month in which you can book a flight from Virginia to Caribbean Islands (average of $113). Flying from Virginia to Caribbean Islands in June is currently the most expensive (average of $214). 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 Islands

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 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$264FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$90Average$397FlexibilityNo cancel feeOn-time65%
DeltaCheapest$146Average$551FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$183Average$494FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$225Average$580FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$614FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$245Average$652FlexibilityNo cancel feeOn-time63%

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