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$219+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Round-trip from

$445
(American Airlines)

One-way from

$219
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$383
From Williamsburg to Caribbean
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One-way flight from Williamsburg to Caribbean
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Highest demand for flights based on searches. 13% potential increase in price ($107 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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 6/137:59 pmPHF - MBJ
2 stops18h 26mAmerican Airlines
Thu 6/192:25 pmMBJ - PHF
2 stops19h 08mAmerican Airlines
Deal found 4/23$445
This American Airlines deal was found by Cheapflights users on 4/23. 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 8/108:15 pmPHF - PUJ
2 stops18h 41mAmerican Airlines
Sat 8/163:30 pmPUJ - PHF
2 stops19h 00mAmerican Airlines
Deal found 4/23$473
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/215:00 amPHF - STT
1 stop5h 49mAmerican Airlines
Thu 6/2611:29 amSTT - PHF
1 stop8h 00mAmerican Airlines
Deal found 4/23$503
This American Airlines deal was found by Cheapflights users on 4/23. 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 7/37:59 pmPHF - PLS
1 stop16h 26mAmerican Airlines
Sun 7/63:20 pmPLS - PHF
1 stop9h 01mAmerican Airlines
Deal found 4/23$547
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/267:59 pmPHF - SXM
2 stops17h 35mAmerican Airlines
Sun 6/292:34 pmSXM - PHF
2 stops28h 55mAmerican Airlines
Deal found 4/23$597
This American Airlines deal was found by Cheapflights users on 4/23. 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 5/308:17 pmPHF - GND
2 stops42h 13mAmerican Airlines
Mon 6/23:30 pmGND - PHF
2 stops19h 14mAmerican Airlines
Deal found 4/23$674
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Mon 6/233:47 pmPHF - SJU
1 stop8h 21mAmerican Airlines
Tue 7/13:45 pmSJU - PHF
1 stop8h 14mAmerican Airlines
Deal found 4/22$754
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/73:47 pmPHF - UVF
2 stops21h 58mAmerican Airlines
Sat 6/142:00 pmUVF - PHF
2 stops29h 29mAmerican Airlines
Deal found 4/23$1,143

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 April 24, 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

Fri 6/13

7:59 pm-1:25 pm

2 stops18h 26m

Montego Bay Sangster Intl

Thu 6/19

2:25 pm-10:33 am

2 stops19h 08m

$445

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

Sun 8/10

8:15 pm-2:56 pm

2 stops18h 41m

Punta Cana

Sat 8/16

3:30 pm-10:30 am

2 stops19h 00m

$473

Newport NewsSaint Thomas Island

PHF - STT

PHFSTT

Newport News Intl

Sat 6/21

5:00 am-10:49 am

1 stop5h 49m

Saint Thomas Island Cyril E King

Thu 6/26

11:29 am-7:29 pm

1 stop8h 00m

$503

Newport NewsProvidenciales

PHF - PLS

PHFPLS

Newport News Intl

Thu 7/3

7:59 pm-12:25 pm

1 stop16h 26m

Providenciales

Sun 7/6

3:20 pm-12:21 am

1 stop9h 01m

$547

Newport NewsSimpson Bay

PHF - SXM

PHFSXM

Newport News Intl

Thu 6/26

7:59 pm-1:34 pm

2 stops17h 35m

Simpson Bay Princess Juliana

Sun 6/29

2:34 pm-7:29 pm

2 stops28h 55m

$597

Newport NewsSt. George's

PHF - GND

PHFGND

Newport News Intl

Fri 5/30

8:17 pm-2:30 pm

2 stops42h 13m

St. George's Point Saline Intl

Mon 6/2

3:30 pm-10:44 am

2 stops19h 14m

$674

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Mon 6/23

3:47 pm-12:08 am

1 stop8h 21m

San Juan Luis Munoz Marin Intl

Tue 7/1

3:45 pm-11:59 pm

1 stop8h 14m

$754

Newport NewsCastries

PHF - UVF

PHFUVF

Newport News Intl

Sat 6/7

3:47 pm-1:45 pm

2 stops21h 58m

Castries Hewanorra

Sat 6/14

2:00 pm-7:29 pm

2 stops29h 29m

$1,143

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Tue 4/29

8:06 pm-10:50 am

1 stop14h 44m

$219

Newport NewsSaint Thomas Island

PHF - STT

PHFSTT

Newport News Intl

Tue 4/29

6:21 am-2:28 pm

1 stop8h 07m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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 December is currently the most expensive (average of $336). 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 April 24, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 24, 2025.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Comfort

7.2

Boarding

7.5

Food

6.5

Overall

7.2

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2025

MYR - CLT

This flight was impacted by a nearly 4, yes 4 hour delay. They replaced a 777 with another one and it had to be cleaned and catered before we could depart. Great crew did it without complaint.

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.

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

    The most popular route from Williamsburg to Caribbean is Newport News Intl - Saint Thomas Island Cyril E King. You may also consider Newport News Intl - Montego Bay Sangster Intl 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, 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 December is currently the most expensive (average of $336). 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$423FlexibilityNo cancel feeOn-time65%
FrontierCheapest$130Average$231FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$611FlexibilityNo cancel feeOn-time69%
DeltaCheapest$233Average$519FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$255Average$602FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$255Average$579FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$359Average$616FlexibilityNo cancel feeOn-time63%

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