HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$144+ Cheap flights from Williamsburg, VA 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Aug 27 — Sep 31
Wed 8/27
Wed 9/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Williamsburg to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Williamsburg to Caribbean

Keep the following information in mind while searching for Williamsburg to Caribbean flight deals. Data was last updated August 22, 2025.

Round-trip from

$399
(American Airlines)

One-way from

$144
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$664
From Williamsburg to Caribbean
Search Deals
One-way flight from Williamsburg to Caribbean
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Williamsburg to Caribbean

Cheapest flights from Williamsburg to Caribbean
Explore the most affordable flight options available from Williamsburg to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/97:59 pmPHF - NAS
1 stop14h 01mAmerican Airlines
Mon 10/136:45 pmNAS - PHF
2 stops17h 36mAmerican Airlines
Deal found 8/20$399
This American Airlines deal was found by Cheapflights users on 8/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/173:51 pmPHF - SJU
1 stop8h 03mAmerican Airlines
Mon 10/207:10 amSJU - PHF
1 stop8h 16mAmerican Airlines
Deal found 8/19$459
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/58:00 pmPHF - MBJ
1 stop14h 13mAmerican Airlines
Sun 10/123:20 pmMBJ - PHF
2 stops18h 36mAmerican Airlines
Deal found 8/21$476
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amPHF - PUJ
1 stop8h 15mAmerican Airlines
Sat 8/304:49 pmPUJ - PHF
2 stops22h 06mAmerican Airlines
Deal found 8/20$535
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/174:03 pmPHF - PUJ
2 stops18h 47mAmerican Airlines
Wed 9/244:25 pmPUJ - PHF
1 stop6h 40mAmerican Airlines
Deal found 8/20$542
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/303:40 pmPHF - SJU
1 stop7h 30mAmerican Airlines
Fri 9/54:43 pmSJU - PHF
1 stop6h 22mAmerican Airlines
Deal found 8/21$575
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/297:59 pmPHF - PUJ
1 stop16h 41mAmerican Airlines
Sun 9/712:08 pmPUJ - PHF
2 stops24h 00mAmerican Airlines
Deal found 8/20$633
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/86:31 amPHF - CUR
1 stop6h 39mAmerican Airlines
Thu 12/113:30 pmCUR - PHF
1 stop7h 23mAmerican Airlines
Deal found 8/20$663
This American Airlines deal was found by Cheapflights users on 8/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/236:07 pmPHF - AUA
2 stops19h 38mAmerican Airlines
Wed 8/274:05 pmAUA - PHF
1 stop6h 57mAmerican Airlines
Deal found 8/22$688
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3011:05 amPHF - SJU
1 stop12h 05mAmerican Airlines
Sat 9/64:45 pmSJU - PHF
1 stop6h 22mAmerican Airlines
Deal found 8/21$730
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:28 amPHF - NAS
1 stop8h 47mAmerican Airlines
Sat 12/274:55 pmNAS - PHF
1 stop15h 40mAmerican Airlines
Deal found 8/20$769
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:23 pmPHF - GND
2 stops25h 32mAmerican Airlines
Wed 12/104:20 pmGND - PHF
2 stops30h 33mAmerican Airlines
Deal found 8/20$917

Cheapflights Fare Finder

 
Customize your flight search to find flights from Williamsburg 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 August 22, 2025.
Use the filters below to find and compare flights from Williamsburg to Caribbean that are best for you.

Fly from

Williamsburg

Fly to

Caribbean

Route

Depart

Return

Price

Newport NewsNassau

PHF - NAS

PHFNAS

Newport News Intl

Thu 10/9

7:59 pm-10:00 am

1 stop14h 01m

Nassau Intl

Mon 10/13

6:45 pm-12:21 pm

2 stops17h 36m

$399

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Fri 10/17

3:51 pm-11:54 pm

1 stop8h 03m

San Juan Luis Munoz Marin Intl

Mon 10/20

7:10 am-3:26 pm

1 stop8h 16m

$459

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Sun 10/5

8:00 pm-9:13 am

1 stop14h 13m

Montego Bay Sangster Intl

Sun 10/12

3:20 pm-10:56 am

2 stops18h 36m

$476

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

Wed 9/17

4:03 pm-10:50 am

2 stops18h 47m

Punta Cana

Wed 9/24

3:35 pm-10:53 am

2 stops19h 18m

$542

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Mon 9/1

5:00 am-2:55 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Fri 9/5

4:43 pm-11:05 pm

1 stop6h 22m

$575

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Sun 8/31

8:50 am-11:10 pm

1 stop14h 20m

San Juan Luis Munoz Marin Intl

Fri 9/5

4:43 pm-11:05 pm

1 stop6h 22m

$575

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Sat 2/14

8:15 pm-11:45 am

1 stop14h 30m

San Juan Luis Munoz Marin Intl

Fri 2/20

4:45 pm-9:46 pm

1 stop6h 01m

$601

Newport NewsWillemstad

PHF - CUR

PHFCUR

Newport News Intl

Mon 12/8

5:00 am-2:10 pm

1 stop8h 10m

Willemstad Hato Int.

Thu 12/11

3:30 pm-9:53 pm

1 stop7h 23m

$663

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Sun 8/31

3:40 pm-11:10 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Sat 9/6

4:45 pm-11:07 pm

1 stop6h 22m

$730

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Mon 9/1

5:00 am-2:55 pm

1 stop9h 55m

San Juan Luis Munoz Marin Intl

Sat 9/6

4:45 pm-11:07 pm

1 stop6h 22m

$730

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 28 results
1
2
3

Best time to book a flight from Williamsburg to Caribbean

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

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

Currently, September is the cheapest month in which you can book a flight from Williamsburg to Caribbean (average of $254). Flying from Williamsburg 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 W11 to CB?

Find hourly flight availability from Williamsburg 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 August 22, 2025.

When flying from Williamsburg to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 22, 2025.
Read reviews from past customers who have flown American Airlines from Williamsburg to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Entertainment

6.9

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Entertainment

6.9

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

Find useful and relevant information for your journey from Williamsburg 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 Williamsburg to Caribbean?

    American Airlines can get you from Williamsburg to Caribbean in just under 14h 01m. Your travel time can differ by up to . Airlines will cover a distance of 836 mi.

  • What are the most popular routes from Williamsburg to Caribbean?

    The most popular route from Williamsburg to Caribbean is Newport News Intl - San Juan Luis Munoz Marin Intl. You may also consider Newport News Intl - Saint Thomas Island Cyril E King or Newport News Intl - Punta Cana.

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

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

  • How can I find direct flights from Williamsburg to Caribbean?

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

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

    Yes. Cheapflights offers flight deals from Williamsburg 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 Williamsburg to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Williamsburg to Caribbean (average of $254). Flying from Williamsburg 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Williamsburg to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Atlanta flights
Reagan-National to O'Hare Intl flights
Reagan-National to Dallas/Fort Worth flights
Dulles Intl to Cancún flights
Dulles Intl to Miami flights
Reagan-National to Los Angeles flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Las Vegas flights
Dulles Intl to Los Angeles flights
Dulles Intl to Boston flights
Dulles Intl to Seattle flights
Raleigh to LaGuardia flights
Reagan-National to Las Vegas flights
Dulles Intl to Heathrow flights
Reagan-National to Seattle flights
Dulles Intl to Orlando flights
Dulles Intl to San Francisco flights
Reagan-National to Atlanta flights
Dulles Intl to Minneapolis flights
Reagan-National to San Francisco flights
Reagan-National to Hobby flights
Reagan-National to Minneapolis flights
Raleigh to John F Kennedy Intl flights
Reagan-National to Boston flights
Dulles Intl to Luis Munoz Marin Intl flights
Raleigh to Las Vegas flights
Reagan-National to Cancún flights
Reagan-National to Denver flights
Dulles Intl to Midway flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to New Orleans flights
Reagan-National to Miami flights
Dulles Intl to Hobby flights
Dulles Intl to Denver flights
Dulles Intl to Tampa flights
Raleigh to Newark flights
Dulles Intl to Mexico City flights
Reagan-National to Orlando flights
Dulles Intl to Haneda flights
Raleigh to O'Hare Intl flights
Dulles Intl to Charles de Gaulle flights
Dulles Intl to San Salvador flights
Dulles Intl to San Diego flights
Dulles Intl to George Bush Intcntl flights
Dulles Intl to Leonardo da Vinci/Fiumicino flights
Raleigh to Boston flights
Raleigh to Denver flights
Dulles Intl to Detroit flights
Reagan-National to George Bush Intcntl flights

Top 7 airlines flying from Williamsburg to Caribbean

Discover the top 7 airlines that operate flights from Williamsburg 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 August 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$294FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$427FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$564FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$603FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$527FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$586FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$264Average$641FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.