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Caribbean

$153+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
RIC — SJU
feb. 26 — mar. 51
jue. 2/26
jue. 3/5
1 adult, Economy
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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 enero 27, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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.
mié. 4/15:00 am
PHF
-
SJU
1 stop10h 28m
American Airlines
mié. 4/154:30 pm
SJU
-
PHF
1 stop7h 29m
American Airlines
Deal found 1/26$305
This American Airlines deal was found by Cheapflights users on 1/27. 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.
jue. 2/267:55 pm
PHF
-
SDQ
2 stops19h 12m
American Airlines
mié. 3/47:00 am
SDQ
-
PHF
2 stops17h 24m
American Airlines
Deal found 1/27$319
This American Airlines deal was found by Cheapflights users on 1/27. 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.
lun. 2/237:55 pm
PHF
-
NAS
2 stops18h 49m
American Airlines
sáb. 2/2812:09 pm
NAS
-
PHF
2 stops11h 50m
American Airlines
Deal found 1/27$326
This American Airlines deal was found by Cheapflights users on 1/26. 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.
sáb. 7/118:00 pm
PHF
-
MBJ
2 stops18h 58m
American Airlines
sáb. 7/182:15 pm
MBJ
-
PHF
2 stops19h 31m
American Airlines
Deal found 1/26$337
This American Airlines deal was found by Cheapflights users on 1/27. 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.
sáb. 5/167:59 pm
PHF
-
PUJ
2 stops18h 36m
American Airlines
mar. 5/264:17 pm
PUJ
-
PHF
2 stops18h 29m
American Airlines
Deal found 1/27$373
This American Airlines deal was found by Cheapflights users on 1/27. 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.
mié. 2/2512:26 pm
PHF
-
SJU
1 stop7h 13m
American Airlines
mié. 3/48:40 am
SJU
-
PHF
1 stop11h 13m
American Airlines
Deal found 1/27$378
This American Airlines deal was found by Cheapflights users on 1/25. 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. 3/17:55 pm
PHF
-
PUJ
1 stop14h 39m
American Airlines
mar. 3/35:41 pm
PUJ
-
PHF
1 stop6h 43m
American Airlines
Deal found 1/25$379
This American Airlines deal was found by Cheapflights users on 1/25. 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. 2/267:55 pm
PHF
-
PUJ
2 stops19h 00m
American Airlines
mar. 3/35:41 pm
PUJ
-
PHF
1 stop6h 43m
American Airlines
Deal found 1/25$383
This American Airlines deal was found by Cheapflights users on 1/25. 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. 3/17:55 pm
PHF
-
PUJ
1 stop16h 41m
American Airlines
mié. 3/45:41 pm
PUJ
-
PHF
1 stop18h 03m
American Airlines
Deal found 1/25$385
This American Airlines deal was found by Cheapflights users on 1/25. 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. 3/17:55 pm
PHF
-
PUJ
1 stop14h 39m
American Airlines
jue. 3/55:41 pm
PUJ
-
PHF
1 stop7h 18m
American Airlines
Deal found 1/25$389
This American Airlines deal was found by Cheapflights users on 1/25. 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. 2/267:55 pm
PHF
-
PUJ
2 stops19h 00m
American Airlines
mié. 3/45:41 pm
PUJ
-
PHF
1 stop18h 03m
American Airlines
Deal found 1/25$390
This American Airlines deal was found by Cheapflights users on 1/26. 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.
jue. 8/67:59 pm
PHF
-
NAS
1 stop13h 53m
American Airlines
dom. 8/97:05 pm
NAS
-
PHF
2 stops15h 35m
American Airlines
Deal found 1/26$401

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 enero 27, 2026.

Round-trip from

$305
(American Airlines)

One-way from

$153
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$588
From Williamsburg to Caribbean
Search Deals
One-way flight from Williamsburg to Caribbean
Search Deals
Highest demand for flights based on searches. 27% potential increase in price ($258 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 15% potential price decrease ($95 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 enero 27, 2026.
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. 4/1

5:00 am-3:28 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

mié. 4/15

4:30 pm-11:59 pm

1 stop7h 29m

$305

Newport NewsSanto Domingo

PHF - SDQ

PHFSDQ

Newport News Intl

jue. 2/26

7:55 pm-5:50 pm

2 stops20h 55m

Santo Domingo Las Americas

mié. 3/4

5:07 pm-10:44 am

2 stops18h 37m

$319

Newport NewsNassau

PHF - NAS

PHFNAS

Newport News Intl

lun. 2/23

7:55 pm-10:58 am

2 stops15h 03m

Nassau Intl

sáb. 2/28

4:36 pm-11:59 pm

1 stop7h 23m

$326

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

sáb. 7/11

8:00 pm-1:58 pm

2 stops18h 58m

Montego Bay Sangster Intl

sáb. 7/18

2:15 pm-10:46 am

2 stops19h 31m

$337

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

sáb. 2/28

7:55 pm-11:40 am

1 stop14h 45m

San Juan Luis Munoz Marin Intl

mié. 3/4

8:40 am-11:24 pm

1 stop15h 44m

$378

Newport NewsSan Juan

PHF - SJU

PHFSJU

Newport News Intl

mié. 2/25

12:26 pm-8:39 pm

1 stop7h 13m

San Juan Luis Munoz Marin Intl

mié. 3/4

1:58 pm-11:24 pm

1 stop10h 26m

$378

Newport NewsMontego Bay

PHF - MBJ

PHFMBJ

Newport News Intl

lun. 3/23

7:55 pm-10:21 am

1 stop15h 26m

Montego Bay Sangster Intl

mar. 3/31

2:18 pm-11:24 pm

1 stop8h 06m

$438

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

sáb. 5/16

7:59 pm-10:45 am

1 stop14h 46m

Punta Cana

mar. 5/26

3:58 pm-10:46 am

1 stop18h 48m

$445

Newport NewsPunta Cana

PHF - PUJ

PHFPUJ

Newport News Intl

vie. 6/26

5:05 am-3:49 pm

1 stop10h 44m

Punta Cana

mar. 6/30

1:31 pm-10:46 am

2 stops21h 15m

$446

Newport NewsProvidenciales

PHF - PLS

PHFPLS

Newport News Intl

jue. 3/12

5:00 am-2:30 pm

1 stop9h 30m

Providenciales

lun. 3/16

3:30 pm-11:59 pm

1 stop8h 29m

$492

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 31 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 June is currently the most expensive (average of $212). 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.

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 enero 27, 2026.
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
11,197 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,197 reviews
American Airlines
7.2
Good
11,197 reviews

Food

6.4

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 10h 28m. 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 - Punta Cana or Newport News Intl - Castries Hewanorra.

  • What are the cheapest flights from Williamsburg to Caribbean?

    Looking for the cheapest flight from Williamsburg to Caribbean? While on average our users pay $429, our data indicates the cheapest price to be $245. The most popular route (Newport News Intl - San Juan Luis Munoz Marin Intl), is priced around $324.

  • 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 $212). 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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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 enero 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$265FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$90Average$390FlexibilityNo cancel feeOn-time65%
DeltaCheapest$146Average$536FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$204Average$543FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$225Average$575FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$592FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$245Average$648FlexibilityNo cancel feeOn-time63%

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