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Caribbean

$192+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/6. 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 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 stop10h 11mAmerican Airlines
Thu 12/113:50 pmMBJ - PHF
1 stop8h 09mAmerican Airlines
Deal found 11/6$361
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:10 pmPHF - MBJ
2 stops18h 29mAmerican Airlines
Sun 12/142:02 pmMBJ - PHF
2 stops20h 55mAmerican Airlines
Deal found 11/6$371
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/104:26 pmPHF - MBJ
2 stops17h 46mAmerican Airlines
Wed 11/1211:12 amMBJ - PHF
2 stops11h 53mAmerican Airlines
Deal found 11/6$486
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:10 pmPHF - BGI
1 stop17h 24mAmerican Airlines
Wed 12/104:40 pmBGI - PHF
2 stops28h 05mAmerican Airlines
Deal found 11/5$686
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/87:55 amPHF - CUR
1 stop6h 37mAmerican Airlines
Thu 12/113:38 pmCUR - PHF
1 stop9h 21mAmerican Airlines
Deal found 11/5$710
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/77:16 pmPHF - CUR
2 stops20h 24mAmerican Airlines
Thu 11/135:40 pmCUR - PHF
2 stops22h 42mAmerican Airlines
Deal found 11/5$893
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/187:54 amPHF - BGI
2 stops13h 33mAmerican Airlines
Thu 11/277:00 amBGI - PHF
2 stops28h 53mAmerican Airlines
Deal found 11/6$937
This American Airlines deal was found by Cheapflights users on 11/4. 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 12/2711:24 amPHF - SJU
1 stop9h 41mAmerican Airlines
Fri 1/98:20 amSJU - PHF
1 stop8h 06mAmerican Airlines
Deal found 11/4$1,041
This American Airlines deal was found by Cheapflights users on 11/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:03 pmPHF - BGI
1 stop17h 41mAmerican Airlines
Sat 12/274:23 pmBGI - PHF
1 stop8h 36mAmerican Airlines
Deal found 11/5$1,161
This American Airlines deal was found by Cheapflights users on 11/4. 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 - GND
2 stops22h 16mAmerican Airlines
Wed 12/104:04 pmGND - PHF
2 stops19h 56mAmerican Airlines
Deal found 11/4$1,624
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:00 amPHF - SJU
1 stop16h 05mAmerican Airlines
Sun 1/48:35 pmSJU - PHF
2 stops19h 38mAmerican Airlines
Deal found 11/6$1,642
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:03 pmPHF - SJU
2 stops18h 45mAmerican Airlines
Sun 1/48:35 pmSJU - PHF
2 stops19h 38mAmerican Airlines
Deal found 11/6$1,674

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 November 6, 2025.

Round-trip from

$321
(American Airlines)

One-way from

$192
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$634
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 November 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 November 6, 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 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

5:33 pm-11:17 am

2 stops18h 44m

$321

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Sat 12/6

8:10 pm-10:12 am

1 stop14h 02m

Montego Bay Sangster Intl

Thu 12/11

3:50 pm-11:59 pm

1 stop8h 09m

$361

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Sun 12/7

8:10 pm-2:39 pm

2 stops18h 29m

Montego Bay Sangster Intl

Sun 12/14

2:02 pm-10:57 am

2 stops20h 55m

$371

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Wed 4/1

6:29 am-7:45 pm

1 stop13h 16m

San Juan Luis Munoz Marin Intl

Wed 4/15

8:30 am-11:52 pm

1 stop15h 22m

$424

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-11:30 pm

1 stop16h 10m

$430

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Tue 3/10

6:29 am-3:05 pm

1 stop9h 36m

Montego Bay Sangster Intl

Thu 3/12

5:00 pm-9:49 pm

2 stops27h 49m

$460

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Wed 3/25

12:15 pm-7:45 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Wed 4/8

8:30 am-7:33 pm

1 stop11h 03m

$522

Newport NewsSanto Domingo

PHF - SDQ

PHFSDQ

Newport News Intl

Tue 3/3

6:00 am-10:02 am

2 stops27h 02m

Santo Domingo Las Americas

Thu 3/5

11:02 am-10:43 am

2 stops24h 41m

$529

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Tue 1/13

11:42 am-8:50 pm

1 stop8h 08m

San Juan Luis Munoz Marin Intl

Sun 1/18

8:20 am-6:51 pm

1 stop11h 31m

$588

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

1:20 pm-9:49 pm

1 stop8h 29m

$674

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 22 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, May is the cheapest month in which you can book a flight from Williamsburg to Caribbean (average of $113). 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 November 6, 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 November 6, 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
11,040 reviews

Crew

8.0

Entertainment

6.9

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Crew

8.0

Entertainment

6.9

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.4

Reviews

1 / 20
8.0
Excellent

Monica,Nov 2025

JAC - DFW

At least there was an option of entertainment on this flight.

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 16h 56m. Your travel time can differ by up to . Airlines will cover a distance of 1548 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 - Simpson Bay Princess Juliana 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, May is the cheapest month in which you can book a flight from Williamsburg to Caribbean (average of $113). 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

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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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$310FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$108Average$438FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$208Average$596FlexibilityNo cancel feeOn-time69%
DeltaCheapest$231Average$532FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$570FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$240Average$594FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$255Average$641FlexibilityNo cancel feeOn-time63%

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