HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$139+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
ene. 7 — ene. 141
mié. 1/7
mié. 1/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Williamsburg to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 diciembre 8, 2025.

This American Airlines deal was found by Cheapflights users on 12/7. 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.
jue. 12/113:46 pmPHF - AUA
2 stops24h 09mAmerican Airlines
sáb. 12/135:59 pmAUA - PHF
1 stop18h 01mAmerican Airlines
Deal found 12/7$370
This American Airlines deal was found by Cheapflights users on 12/7. 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.
mar. 12/164:26 pmPHF - NAS
2 stops17h 53mAmerican Airlines
lun. 12/227:45 amNAS - PHF
2 stops16h 14mAmerican Airlines
Deal found 12/7$397
This American Airlines deal was found by Cheapflights users on 12/7. 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.
dom. 12/78:10 pmPHF - MBJ
2 stops18h 02mAmerican Airlines
vie. 1/91:58 pmMBJ - PHF
2 stops21h 19mAmerican Airlines
Deal found 12/7$398
This American Airlines deal was found by Cheapflights users on 12/7. 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.
jue. 12/253:42 pmPHF - MBJ
2 stops23h 08mAmerican Airlines
mié. 12/313:51 pmMBJ - PHF
2 stops19h 03mAmerican Airlines
Deal found 12/7$435
This American Airlines deal was found by Cheapflights users on 12/7. 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.
mié. 12/245:00 amPHF - MBJ
2 stops31h 06mAmerican Airlines
mié. 12/313:51 pmMBJ - PHF
2 stops19h 03mAmerican Airlines
Deal found 12/7$448
This American Airlines deal was found by Cheapflights users on 12/7. 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.
jue. 12/253:42 pmPHF - MBJ
2 stops23h 08mAmerican Airlines
mar. 12/302:23 pmMBJ - PHF
2 stops29h 10mAmerican Airlines
Deal found 12/7$450
This American Airlines deal was found by Cheapflights users on 12/7. 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.
mié. 12/245:00 amPHF - MBJ
2 stops33h 51mAmerican Airlines
mar. 12/302:23 pmMBJ - PHF
2 stops29h 10mAmerican Airlines
Deal found 12/7$454
This American Airlines deal was found by Cheapflights users on 12/7. 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.
jue. 12/258:00 amPHF - MBJ
1 stop26h 21mAmerican Airlines
lun. 12/294:24 pmMBJ - PHF
2 stops42h 30mAmerican Airlines
Deal found 12/7$457
This American Airlines deal was found by Cheapflights users on 12/7. 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.
mié. 12/245:00 amPHF - MBJ
2 stops31h 06mAmerican Airlines
lun. 12/294:24 pmMBJ - PHF
2 stops42h 30mAmerican Airlines
Deal found 12/7$463
This American Airlines deal was found by Cheapflights users on 12/7. 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.
lun. 12/228:03 pmPHF - MBJ
2 stops17h 20mAmerican Airlines
mié. 12/313:51 pmMBJ - PHF
2 stops19h 03mAmerican Airlines
Deal found 12/7$474
This American Airlines deal was found by Cheapflights users on 12/7. 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.
mar. 12/2311:24 amPHF - MBJ
2 stops48h 42mAmerican Airlines
mié. 12/3111:12 amMBJ - PHF
2 stops23h 42mAmerican Airlines
Deal found 12/7$487
This American Airlines deal was found by Cheapflights users on 12/8. 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.
lun. 12/298:03 pmPHF - GCM
2 stops18h 46mAmerican Airlines
vie. 1/27:30 amGCM - PHF
2 stops16h 29mAmerican Airlines
Deal found 12/8$824

Find flight deals from Williamsburg to Caribbean

Keep the following information in mind while searching for Williamsburg to Caribbean flight deals. Data was last updated diciembre 8, 2025.

Round-trip from

$231
(American Airlines)

One-way from

$139
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$1,637
From Williamsburg to Caribbean
Search Deals
One-way flight from Williamsburg to Caribbean
Search Deals
Highest demand for flights based on searches. 25% potential increase in price ($241 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($93 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 diciembre 8, 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

mié. 2/25

6:00 am-2:59 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

mié. 3/4

5:51 pm-11:28 pm

1 stop6h 37m

$231

Newport NewsSimpson Bay

PHF - SXM

PHFSXM

Newport News Intl

sáb. 1/3

8:03 pm-2:26 pm

2 stops17h 23m

Simpson Bay Princess Juliana

dom. 1/25

5:33 pm-11:17 am

2 stops18h 44m

$303

Newport NewsNassau

PHF - NAS

PHFNAS

Newport News Intl

jue. 1/29

7:28 am-12:13 pm

1 stop4h 45m

Nassau Intl

lun. 2/2

2:22 pm-6:51 pm

1 stop4h 29m

$325

Newport NewsNassau

PHF - NAS

PHFNAS

Newport News Intl

lun. 2/23

3:43 pm-9:48 am

2 stops18h 05m

Nassau Intl

sáb. 2/28

5:45 pm-10:43 am

2 stops16h 58m

$329

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

dom. 2/1

7:16 pm-1:08 pm

1 stop16h 52m

San Juan Luis Munoz Marin Intl

sáb. 2/7

5:55 pm-11:30 pm

1 stop6h 35m

$353

Newport NewsGeorge Town

PHF - GCM

PHFGCM

Newport News Intl

sáb. 2/14

7:58 pm-3:25 pm

2 stops19h 27m

George Town Owen Roberts Intl

sáb. 2/21

4:25 pm-10:43 am

2 stops18h 18m

$376

Newport NewsGeorge Town

PHF - GCM

PHFGCM

Newport News Intl

dom. 3/8

7:55 pm-7:15 pm

2 stops24h 20m

George Town Owen Roberts Intl

dom. 3/15

2:36 pm-11:59 pm

2 stops32h 23m

$378

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

jue. 1/29

11:42 am-8:50 pm

1 stop8h 08m

San Juan Luis Munoz Marin Intl

sáb. 1/31

8:20 am-3:27 pm

1 stop8h 07m

$426

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

jue. 12/25

3:42 pm-2:50 pm

2 stops23h 08m

Montego Bay Sangster Intl

mié. 12/31

3:51 pm-10:54 am

2 stops19h 03m

$435

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

jue. 12/25

3:42 pm-10:21 am

1 stop18h 39m

Montego Bay Sangster Intl

mar. 12/30

2:23 pm-7:33 pm

2 stops29h 10m

$448

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/7

Showing 1-10 of 38 results
1
2
3
4

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 June is currently the most expensive (average of $208). 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 diciembre 8, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 22% 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 diciembre 8, 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
11,042 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Boarding

7.5

Food

6.5

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit
American Airlines
7.2
Good
11,042 reviews
American Airlines
7.2
Good
11,042 reviews

Crew

8.0

Comfort

7.2

Overall

7.2

Boarding

7.5

Food

6.5

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Jeremy,Dec 2025

OKC - CLT

Was an okay flight. Had extra seat empty beside me so was able to stretch a bit

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 7h 59m. Your travel time can differ by up to . Airlines will cover a distance of 1439 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 - Freeport Grand Bahama Intl 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 June is currently the most expensive (average of $208). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Williamsburg to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Cancún flights
Reagan-National to Miami flights
Dulles Intl to Miami flights
Dulles Intl to Las Vegas flights
Dulles Intl to Dallas/Fort Worth flights
Dulles Intl to Orlando flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Orlando flights
Reagan-National to Los Angeles flights
Reagan-National to Fort Lauderdale flights
Reagan-National to Las Vegas flights
Reagan-National to Cancún flights
Dulles Intl to Los Angeles flights
Dulles Intl to Tampa flights
Reagan-National to Luis Munoz Marin Intl flights
Dulles Intl to Sky Harbor Intl flights
Reagan-National to Dallas/Fort Worth flights
Reagan-National to Hobby flights
Dulles Intl to San Salvador flights
Raleigh to LaGuardia flights
Dulles Intl to Heathrow flights
Reagan-National to Seattle flights
Dulles Intl to Hobby flights
Dulles Intl to Seattle flights
Dulles Intl to Mexico City flights
Dulles Intl to Haneda flights
Dulles Intl to Denver flights
Raleigh to Dallas/Fort Worth flights
Dulles Intl to Atlanta flights
Reagan-National to Tampa flights
Dulles Intl to Charles de Gaulle flights
Dulles Intl to San Francisco flights
Raleigh to John F Kennedy Intl flights
Dulles Intl to O'Hare Intl flights
Raleigh to Miami flights
Dulles Intl to New Orleans flights
Reagan-National to Atlanta flights
Dulles Intl to Salt Lake City flights
Dulles Intl to Punta Cana flights
Reagan-National to Boston flights
Reagan-National to O'Hare Intl flights
Reagan-National to Salt Lake City flights
Reagan-National to San Francisco flights
Dulles Intl to George Bush Intcntl flights
Reagan-National to Sky Harbor Intl flights
Raleigh to Las Vegas flights
Dulles Intl to Leonardo da Vinci/Fiumicino flights
Dulles Intl to Honolulu flights
Reagan-National to George Bush Intcntl flights

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 diciembre 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$90Average$419FlexibilityNo cancel feeOn-time65%
DeltaCheapest$214Average$538FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$225Average$606FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$229Average$596FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$236Average$552FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$250Average$627FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.