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Caribbean Islands

$654+ Cheap flights from Staunton (SHD) to Caribbean Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
SHD — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Staunton to Caribbean Islands

Keep the following information in mind while searching for Staunton to Caribbean Islands flight deals. Data was last updated October 28, 2025.

Round-trip from

$654
(American Airlines)
From Staunton Shenandoah Valley to Caribbean Islands
Search Deals

Find flight deals from Staunton to Caribbean Islands

Best flights from Staunton to Caribbean Islands
Discover carefully curated flight deals from Staunton to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 3/2912:45 pmSHD - POP
2 stops25h 20mAmerican Airlines
Wed 4/13:30 pmPOP - SHD
1 stop20h 45mAmerican Airlines
Deal found 10/26$654
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 3/105:15 amSHD - SJU
1 stop9h 15mAmerican Airlines
Wed 3/113:45 pmSJU - SHD
2 stops20h 30mAmerican Airlines
Deal found 10/26$783

Cheapflights Fare Finder

 
Customize your flight search to find flights from Staunton to Caribbean Islands 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 October 28, 2025.
Use the filters below to find and compare flights from Staunton to Caribbean Islands that are best for you.

Fly from

Staunton

Fly to

Caribbean Islands

Route

Depart

Return

Price

StauntonPuerto Plata

SHD - POP

SHDPOP

Staunton Shenandoah Valley

Sun 3/29

12:45 pm-2:05 pm

2 stops25h 20m

Puerto Plata La Union

Wed 4/1

3:30 pm-12:15 pm

1 stop20h 45m

$654

StauntonSan Juan

SHD - SJU

SHDSJU

Staunton Shenandoah Valley

Tue 3/10

5:15 am-2:30 pm

1 stop9h 15m

San Juan Luis Munoz Marin Intl

Wed 3/11

3:45 pm-12:15 pm

2 stops20h 30m

$783

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Best time to book a flight from Staunton to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Staunton 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 Staunton to Caribbean Islands

What is the cheapest month to book a flight from Staunton to Caribbean Islands?

Currently, January is the cheapest month in which you can book a flight from Staunton to Caribbean Islands (average of $217). Flying from Staunton to Caribbean Islands in July is currently the most expensive (average of $422). 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.

Related info for your journey

Find useful and relevant information for your journey from Staunton to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Staunton to Caribbean Islands?

    Staunton Shenandoah Valley (SHD) is the airport you will fly out of if you book a flight from Staunton to Caribbean Islands. It is only a 12.1 mi journey to Shenandoah Valley (SHD) from Staunton’s city center.

  • How long is the flight from Staunton to Caribbean Islands?

    A quick flight from Staunton to Caribbean Islands can take about 25h 20m. American Airlines provides one of the quickest options available for as low as $654. Airlines will cover a distance of 1372 mi.

  • Can I find deals for flights from Staunton to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Staunton to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Staunton to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Staunton to Caribbean Islands.

  • Can I find deals for business class flights from Staunton to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Staunton to Caribbean Islands 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 Staunton to Caribbean Islands?

    Currently, January is the cheapest month in which you can book a flight from Staunton to Caribbean Islands (average of $217). Flying from Staunton to Caribbean Islands in July is currently the most expensive (average of $422). 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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