HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$303+ 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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
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.

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 October 22, 2025.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:16 pmPHF - PUJ
2 stops18h 16mAmerican Airlines
Fri 12/124:11 pmPUJ - PHF
1 stop7h 55mAmerican Airlines
Deal found 10/20$306
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:46 pmPHF - NAS
2 stops18h 33mAmerican Airlines
Thu 12/113:00 pmNAS - PHF
1 stop8h 59mAmerican Airlines
Deal found 10/20$333
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/66:10 amPHF - MBJ
1 stop8h 28mAmerican Airlines
Thu 12/113:50 pmMBJ - PHF
1 stop8h 09mAmerican Airlines
Deal found 10/21$361
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amPHF - STT
1 stop6h 00mAmerican Airlines
Mon 11/31:36 pmSTT - PHF
1 stop10h 29mAmerican Airlines
Deal found 10/20$472
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/228:12 pmPHF - MBJ
1 stop13h 56mAmerican Airlines
Sat 12/61:55 pmMBJ - PHF
1 stop10h 04mAmerican Airlines
Deal found 10/21$475
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:14 pmPHF - MBJ
2 stops17h 46mAmerican Airlines
Sun 10/264:22 pmMBJ - PHF
1 stop6h 44mAmerican Airlines
Deal found 10/20$491
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Sun 10/263:51 pmPHF - SJU
1 stop8h 03mAmerican Airlines
Mon 10/277:10 amSJU - PHF
1 stop12h 24mAmerican Airlines
Deal found 10/19$528
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:00 pmPHF - MBJ
2 stops22h 00mAmerican Airlines
Mon 11/34:28 pmMBJ - PHF
2 stops18h 15mAmerican Airlines
Deal found 10/20$604
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/63:46 pmPHF - FPO
2 stops22h 28mAmerican Airlines
Sat 12/132:54 pmFPO - PHF
2 stops20h 06mAmerican Airlines
Deal found 10/21$622
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:03 pmPHF - SJU
1 stop14h 36mAmerican Airlines
Sun 12/218:25 amSJU - PHF
1 stop16h 34mAmerican Airlines
Deal found 10/21$908

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 October 22, 2025.

Round-trip from

$306
(American Airlines)

One-way from

$303
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$644
From Williamsburg to Caribbean
Search Deals
One-way flight from Williamsburg to Caribbean
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($149 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($55 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 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 October 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 NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

Fri 12/5

7:16 pm-2:32 pm

2 stops18h 16m

Punta Cana

Fri 12/12

12:53 pm-11:06 pm

2 stops11h 13m

$306

Newport NewsSimpson Bay

PHF - SXM

PHFSXM

Newport News Intl

Sat 1/3

8:03 pm-1:59 pm

1 stop16h 56m

Simpson Bay Princess Juliana

Sun 1/25

2:03 pm-11:17 am

2 stops22h 14m

$321

Newport NewsNassau

PHF - NAS

PHFNAS

Newport News Intl

Thu 12/4

3:46 pm-10:19 am

2 stops18h 33m

Nassau Intl

Thu 12/11

12:07 pm-11:59 pm

2 stops11h 52m

$333

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Sat 12/6

8:10 pm-12:55 pm

1 stop16h 45m

Montego Bay Sangster Intl

Thu 12/11

11:12 am-7:45 pm

1 stop8h 33m

$361

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

Sun 4/5

8:06 pm-12:40 pm

2 stops16h 34m

Punta Cana

Wed 4/8

3:15 pm-10:37 am

2 stops19h 22m

$366

Newport NewsSanto Domingo

PHF - SDQ

PHFSDQ

Newport News Intl

Mon 2/23

12:23 pm-3:30 pm

2 stops26h 07m

Santo Domingo Las Americas

Sat 2/28

6:45 am-9:46 pm

2 stops16h 01m

$406

Newport NewsSanto Domingo

PHF - SDQ

PHFSDQ

Newport News Intl

Sun 2/22

8:15 pm-11:00 pm

2 stops25h 45m

Santo Domingo Las Americas

Sat 2/28

8:50 am-10:34 am

2 stops26h 44m

$406

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Sun 2/1

7:16 pm-1:08 pm

1 stop16h 52m

San Juan Luis Munoz Marin Intl

Sat 2/7

8:20 am-6:51 pm

1 stop11h 31m

$407

Newport NewsSanto Domingo

PHF - SDQ

PHFSDQ

Newport News Intl

Tue 3/3

8:15 pm-1:20 pm

2 stops16h 05m

Santo Domingo Las Americas

Thu 3/5

4:20 pm-9:46 pm

2 stops30h 26m

$421

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Wed 4/1

8:06 pm-10:40 am

1 stop14h 34m

San Juan Luis Munoz Marin Intl

Wed 4/15

11:45 am-11:52 pm

1 stop12h 07m

$465

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 25 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, May is the cheapest month in which you can book a flight from Williamsburg to Caribbean (average of $109). Flying from Williamsburg 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 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 October 22, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 23% on flights from Williamsburg to Caribbean by exploring options for tickets in the evening.

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

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

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

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 October 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
11,029 reviews

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,029 reviews
American Airlines
7.2
Good
11,029 reviews

Boarding

7.5

Crew

8.0

Food

6.4

Overall

7.2

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 18h 16m. Your travel time can differ by up to . Airlines will cover a distance of 1373 mi.

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

    The most popular route from Williamsburg to Caribbean is Newport News Intl - Montego Bay Sangster Intl. You may also consider Newport News Intl - Santo Domingo Las Americas or Newport News Intl - San Juan Luis Munoz Marin Intl.

  • 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, May is the cheapest month in which you can book a flight from Williamsburg to Caribbean (average of $109). Flying from Williamsburg 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

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 Las Vegas flights
Dulles Intl to Cancún flights
Dulles Intl to Miami flights
Dulles Intl to Dallas/Fort Worth flights
Reagan-National to Miami flights
Reagan-National to Las Vegas flights
Dulles Intl to Orlando flights
Dulles Intl to Atlanta flights
Reagan-National to Dallas/Fort Worth flights
Dulles Intl to Los Angeles flights
Reagan-National to Los Angeles flights
Dulles Intl to Luis Munoz Marin Intl flights
Dulles Intl to Hobby flights
Dulles Intl to Heathrow flights
Reagan-National to Atlanta flights
Reagan-National to O'Hare Intl flights
Reagan-National to Hobby flights
Dulles Intl to O'Hare Intl flights
Reagan-National to Orlando flights
Dulles Intl to Mexico City flights
Raleigh to John F Kennedy Intl flights
Reagan-National to Cancún flights
Dulles Intl to New Orleans flights
Raleigh to Miami flights
Raleigh to LaGuardia flights
Reagan-National to Fort Lauderdale flights
Reagan-National to San Francisco flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to Sky Harbor Intl flights
Dulles Intl to Tampa flights
Dulles Intl to Boston flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to Boston flights
Dulles Intl to Charles de Gaulle flights
Raleigh to Newark flights
Reagan-National to Tampa flights
Reagan-National to Seattle flights
Dulles Intl to Haneda flights
Dulles Intl to Madrid flights
Dulles Intl to San Francisco flights
Raleigh to Orlando flights
Reagan-National to New Orleans flights
Raleigh to Dallas/Fort Worth flights
Dulles Intl to Denver flights
Dulles Intl to Seattle flights
Reagan-National to George Bush Intcntl flights
Dulles Intl to Detroit flights
Raleigh to Boston flights
Dulles Intl to San Salvador 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 October 22, 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$584FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$529FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$244Average$588FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$615FlexibilityNo 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.