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Caribbean

$201+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$395
(American Airlines)

One-way from

$201
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$609
From Williamsburg to Caribbean
Search Deals
One-way flight from Williamsburg to Caribbean
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Highest demand for flights based on searches. 3% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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 11/13:51 pmPHF - MBJ
1 stop22h 03mAmerican Airlines
Thu 11/63:50 pmMBJ - PHF
1 stop8h 08mAmerican Airlines
Deal found 9/14$395
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/296:00 amPHF - PUJ
1 stop9h 29mAmerican Airlines
Wed 11/53:02 pmPUJ - PHF
1 stop9h 03mAmerican Airlines
Deal found 9/14$398
This American Airlines deal was found by Cheapflights users on 9/15. 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 - MBJ
2 stops17h 01mAmerican Airlines
Sat 10/112:30 pmMBJ - PHF
2 stops19h 26mAmerican Airlines
Deal found 9/15$505
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/298:03 pmPHF - MBJ
2 stops17h 15mAmerican Airlines
Thu 1/11:16 pmMBJ - PHF
2 stops21h 38mAmerican Airlines
Deal found 9/15$559
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/293:42 pmPHF - AUA
2 stops21h 57mAmerican Airlines
Sun 1/44:50 pmAUA - PHF
2 stops19h 04mAmerican Airlines
Deal found 9/14$597
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/298:03 pmPHF - PUJ
2 stops19h 01mAmerican Airlines
Thu 1/16:02 pmPUJ - PHF
2 stops17h 52mAmerican Airlines
Deal found 9/15$642
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/227:14 pmPHF - FPO
2 stops18h 25mAmerican Airlines
Mon 10/272:21 pmFPO - PHF
2 stops22h 00mAmerican Airlines
Deal found 9/14$651
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/298:03 pmPHF - AUA
2 stops19h 47mAmerican Airlines
Mon 1/52:51 pmAUA - PHF
2 stops20h 42mAmerican Airlines
Deal found 9/15$662
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/253:42 pmPHF - MBJ
2 stops21h 36mAmerican Airlines
Thu 1/11:16 pmMBJ - PHF
2 stops21h 38mAmerican Airlines
Deal found 9/15$672
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/298:03 pmPHF - MBJ
2 stops17h 15mAmerican Airlines
Sun 1/46:06 pmMBJ - PHF
2 stops25h 27mAmerican Airlines
Deal found 9/15$683
This American Airlines deal was found by Cheapflights users on 9/15. 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 - MBJ
2 stops17h 01mAmerican Airlines
Mon 10/133:00 pmMBJ - PHF
1 stop8h 06mAmerican Airlines
Deal found 9/15$687
This American Airlines deal was found by Cheapflights users on 9/15. 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 - MBJ
2 stops17h 01mAmerican Airlines
Sun 10/123:00 pmMBJ - PHF
1 stop8h 06mAmerican Airlines
Deal found 9/15$692

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 September 15, 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 NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Sat 11/1

3:51 pm-12:54 pm

1 stop22h 03m

Montego Bay Sangster Intl

Thu 11/6

3:50 pm-11:58 pm

1 stop8h 08m

$395

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

Wed 10/29

6:00 am-3:29 pm

1 stop9h 29m

Punta Cana

Wed 11/5

3:02 pm-11:05 pm

1 stop9h 03m

$398

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Sun 2/1

8:17 pm-11:45 am

1 stop14h 28m

San Juan Luis Munoz Marin Intl

Sat 2/7

4:40 pm-11:52 pm

1 stop8h 12m

$405

Newport NewsOranjestad

PHF - AUA

PHFAUA

Newport News Intl

Fri 1/23

8:17 pm-4:00 pm

2 stops18h 43m

Oranjestad Reina Beatrix

Fri 1/30

5:00 pm-11:52 pm

1 stop7h 52m

$452

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Tue 3/10

8:06 pm-9:15 am

1 stop14h 09m

Montego Bay Sangster Intl

Thu 3/12

5:00 pm-9:49 pm

2 stops27h 49m

$459

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Tue 1/6

8:17 pm-12:05 pm

1 stop15h 48m

Montego Bay Sangster Intl

Sun 1/18

11:50 am-9:46 pm

1 stop9h 56m

$461

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Tue 3/10

8:06 pm-10:40 am

1 stop14h 34m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:35 pm-9:49 pm

1 stop6h 14m

$530

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Mon 12/29

8:03 pm-1:18 pm

2 stops17h 15m

Montego Bay Sangster Intl

Thu 1/1

1:16 pm-10:54 am

2 stops21h 38m

$559

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Mon 12/29

8:03 pm-1:18 pm

2 stops17h 15m

Montego Bay Sangster Intl

Mon 1/5

6:06 pm-10:33 am

2 stops16h 27m

$559

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Tue 3/10

8:06 pm-10:40 am

1 stop14h 34m

San Juan Luis Munoz Marin Intl

Thu 3/12

8:25 am-9:49 pm

1 stop13h 24m

$590

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 32 results
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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 September 15, 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 September 15, 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

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

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 22h 03m. Your travel time can differ by up to . Airlines will cover a distance of 1289 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 - Punta Cana or Newport News Intl - Montego Bay Sangster 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, 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

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$428FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$204Average$560FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$590FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$525FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$605FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$647FlexibilityNo cancel feeOn-time63%

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