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$180+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Round-trip from

$439
(American Airlines)

One-way from

$180
(American Airlines)

Popular in

August

Cheapest in

April

Average price

$597
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. 3% potential increase in price ($28 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 March 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 March 28, 2025.

This American Airlines deal was found by Cheapflights users on 3/27. 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 6/216:09 pmPHF - STT
1 stop16h 40mAmerican Airlines
Thu 6/2611:29 amSTT - PHF
1 stop8h 00mAmerican Airlines
Deal found 3/27$439
This American Airlines deal was found by Cheapflights users on 3/27. 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 5/118:17 pmPHF - NAS
2 stops14h 53mAmerican Airlines
Sun 5/187:45 amNAS - PHF
2 stops16h 05mAmerican Airlines
Deal found 3/27$456
This American Airlines deal was found by Cheapflights users on 3/27. 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 - PUJ
2 stops16h 26mAmerican Airlines
Tue 7/11:25 pmPUJ - PHF
2 stops21h 08mAmerican Airlines
Deal found 3/27$487
This American Airlines deal was found by Cheapflights users on 3/26. 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 3/278:06 pmPHF - MBJ
1 stop14h 09mAmerican Airlines
Tue 4/110:15 amMBJ - PHF
1 stop10h 57mAmerican Airlines
Deal found 3/26$538
This American Airlines deal was found by Cheapflights users on 3/27. 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 8/295:00 amPHF - PLS
1 stop9h 05mAmerican Airlines
Mon 9/111:20 amPLS - PHF
1 stop12h 36mAmerican Airlines
Deal found 3/27$542
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/86:21 amPHF - SJU
1 stop8h 24mAmerican Airlines
Tue 4/1511:45 amSJU - PHF
1 stop12h 06mAmerican Airlines
Deal found 3/27$586
This American Airlines deal was found by Cheapflights users on 3/27. 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
1 stop17h 21mAmerican Airlines
Sun 6/292:30 pmSXM - PHF
2 stops28h 59mAmerican Airlines
Deal found 3/27$597
This American Airlines deal was found by Cheapflights users on 3/27. 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 6/307:59 pmPHF - CUR
2 stops17h 46mAmerican Airlines
Sat 7/54:15 pmCUR - PHF
2 stops18h 23mAmerican Airlines
Deal found 3/27$782

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 March 28, 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 NewsSaint Thomas Island

PHF - STT

PHFSTT

Newport News Intl

Sat 6/21

6:09 pm-10:49 am

1 stop16h 40m

Saint Thomas Island Cyril E King

Thu 6/26

11:29 am-7:29 pm

1 stop8h 00m

$439

Newport NewsNassau

PHF - NAS

PHFNAS

Newport News Intl

Sun 5/11

8:17 pm-11:10 am

2 stops14h 53m

Nassau Intl

Sun 5/18

7:45 am-11:50 pm

2 stops16h 05m

$456

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

Thu 6/26

7:59 pm-12:25 pm

2 stops16h 26m

Punta Cana

Tue 7/1

1:25 pm-10:33 am

2 stops21h 08m

$487

Newport NewsProvidenciales

PHF - PLS

PHFPLS

Newport News Intl

Fri 8/29

5:00 am-2:05 pm

1 stop9h 05m

Providenciales

Mon 9/1

11:20 am-11:56 pm

1 stop12h 36m

$542

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Tue 4/8

6:21 am-2:45 pm

1 stop8h 24m

San Juan Luis Munoz Marin Intl

Tue 4/15

11:45 am-11:51 pm

1 stop12h 06m

$586

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Wed 4/23

8:06 pm-11:55 am

2 stops16h 49m

Montego Bay Sangster Intl

Sat 4/26

12:55 pm-10:52 am

2 stops20h 57m

$589

Newport NewsSimpson Bay

PHF - SXM

PHFSXM

Newport News Intl

Thu 6/26

7:59 pm-1:20 pm

1 stop17h 21m

Simpson Bay Princess Juliana

Sun 6/29

2:30 pm-7:29 pm

2 stops28h 59m

$597

Newport NewsWillemstad

PHF - CUR

PHFCUR

Newport News Intl

Mon 6/30

7:59 pm-1:45 pm

2 stops17h 46m

Willemstad Hato Int.

Sat 7/5

4:15 pm-10:38 am

2 stops18h 23m

$782

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

Thu 4/24

8:06 pm-9:45 am

2 stops14h 39m

$180

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Thu 4/24

8:06 pm-10:50 am

1 stop14h 44m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

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 March 28, 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 March 28, 2025.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Food

6.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Overall

7.2

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Food

6.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Overall

7.2

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation

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 - San Juan Luis Munoz Marin Intl. You may also consider Newport News Intl - Saint Thomas Island Cyril E King or Newport News Intl - Simpson Bay Princess Juliana.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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See prices for flight routes from nearby airports that may be better suited for you.
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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$128Average$390FlexibilityNo cancel feeOn-time65%
FrontierCheapest$135Average$297FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$625FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$599FlexibilityNo cancel feeOn-time71%
DeltaCheapest$232Average$527FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$256Average$579FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$349Average$611FlexibilityNo cancel feeOn-time63%
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