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$211+ 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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$418
(American Airlines)

One-way from

$211
(American Airlines)

Popular in

July

Cheapest in

April

Average price

$919
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. 6% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/3. 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 8/1112:23 pmPHF - SJU
1 stop9h 07mAmerican Airlines
Thu 8/148:00 amSJU - PHF
1 stop11h 29mAmerican Airlines
Deal found 7/3$418
This American Airlines deal was found by Cheapflights users on 7/1. 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 9/64:03 pmPHF - GCM
2 stops20h 07mAmerican Airlines
Sat 9/1312:25 pmGCM - PHF
1 stop9h 42mAmerican Airlines
Deal found 7/1$487
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/245:00 amPHF - AUA
1 stop11h 10mAmerican Airlines
Sun 8/315:05 pmAUA - PHF
2 stops26h 23mAmerican Airlines
Deal found 7/1$560
This American Airlines deal was found by Cheapflights users on 7/1. 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 - SXM
1 stop22h 04mAmerican Airlines
Sat 11/83:30 pmSXM - PHF
2 stops18h 11mAmerican Airlines
Deal found 7/1$586
This American Airlines deal was found by Cheapflights users on 7/2. 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 12/88:18 pmPHF - CUR
1 stop16h 52mAmerican Airlines
Thu 12/113:30 pmCUR - PHF
1 stop9h 27mAmerican Airlines
Deal found 7/2$643
This American Airlines deal was found by Cheapflights users on 7/2. 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 12/68:18 pmPHF - BGI
1 stop17h 22mAmerican Airlines
Wed 12/105:00 pmBGI - PHF
1 stop18h 39mAmerican Airlines
Deal found 7/2$651
This American Airlines deal was found by Cheapflights users on 6/30. 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 8/196:00 amPHF - UVF
1 stop7h 45mAmerican Airlines
Thu 8/212:55 pmUVF - PHF
1 stop9h 11mAmerican Airlines
Deal found 6/30$665
This American Airlines deal was found by Cheapflights users on 7/2. 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 12/63:50 pmPHF - GND
2 stops22h 05mAmerican Airlines
Wed 12/104:20 pmGND - PHF
2 stops28h 12mAmerican Airlines
Deal found 7/2$822
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/1$862
This American Airlines deal was found by Cheapflights users on 7/2. 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 8/18:03 pmPHF - STT
1 stop14h 42mAmerican Airlines
Fri 8/85:10 pmSTT - PHF
2 stops26h 19mAmerican Airlines
Deal found 7/2$1,026

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 July 3, 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 NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Mon 8/11

12:23 pm-9:30 pm

1 stop9h 07m

San Juan Luis Munoz Marin Intl

Thu 8/14

8:00 am-7:29 pm

1 stop11h 29m

$418

Newport NewsGeorge Town

PHF - GCM

PHFGCM

Newport News Intl

Sat 9/6

4:03 pm-11:10 am

2 stops20h 07m

George Town Owen Roberts Intl

Sat 9/13

12:25 pm-11:07 pm

1 stop9h 42m

$487

Newport NewsOranjestad

PHF - AUA

PHFAUA

Newport News Intl

Sun 8/24

5:00 am-4:10 pm

1 stop11h 10m

Oranjestad Reina Beatrix

Sun 8/31

5:05 pm-7:28 pm

2 stops26h 23m

$560

Newport NewsSimpson Bay

PHF - SXM

PHFSXM

Newport News Intl

Sat 11/1

3:51 pm-1:55 pm

1 stop22h 04m

Simpson Bay Princess Juliana

Sat 11/8

3:30 pm-8:41 am

2 stops18h 11m

$586

Newport NewsWillemstad

PHF - CUR

PHFCUR

Newport News Intl

Mon 12/8

8:18 pm-2:10 pm

1 stop16h 52m

Willemstad Hato Int.

Thu 12/11

3:30 pm-11:57 pm

1 stop9h 27m

$643

Newport NewsBridgetown

PHF - BGI

PHFBGI

Newport News Intl

Sat 12/6

8:18 pm-2:40 pm

1 stop17h 22m

Bridgetown Grantley Adams Intl

Wed 12/10

5:00 pm-10:39 am

1 stop18h 39m

$651

Newport NewsCastries

PHF - UVF

PHFUVF

Newport News Intl

Tue 8/19

6:00 am-1:45 pm

1 stop7h 45m

Castries Hewanorra

Thu 8/21

2:55 pm-12:06 am

1 stop9h 11m

$665

Newport NewsSt. George's

PHF - GND

PHFGND

Newport News Intl

Sat 12/6

3:50 pm-2:55 pm

2 stops22h 05m

St. George's Point Saline Intl

Wed 12/10

4:20 pm-7:32 pm

2 stops28h 12m

$822

Newport NewsSaint Thomas Island

PHF - STT

PHFSTT

Newport News Intl

Fri 8/1

8:03 pm-10:45 am

1 stop14h 42m

Saint Thomas Island Cyril E King

Fri 8/8

5:10 pm-7:29 pm

2 stops26h 19m

$1,026

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

Sat 7/26

11:20 am-10:55 pm

1 stop11h 35m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 11 results
1
2

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 July 3, 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 July 3, 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

Boarding

7.5

Crew

8.0

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Crew

8.0

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.5

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.

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 - Providenciales. You may also consider Newport News Intl - San Juan Luis Munoz Marin Intl or Newport News Intl - George Town Owen Roberts 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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$108Average$437FlexibilityNo cancel feeOn-time65%
FrontierCheapest$110Average$281FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$204Average$559FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$208Average$605FlexibilityNo cancel feeOn-time69%
DeltaCheapest$234Average$530FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$257Average$594FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$347Average$656FlexibilityNo cancel feeOn-time63%

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