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$425+ Cheap flights from Hilton Head Island (HHH) to Caribbean

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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Aug 31 — Sep 71
Sun 8/31
Sun 9/7
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Caribbean

Keep the following information in mind while searching for Hilton Head Island to Caribbean flight deals. Data was last updated August 26, 2025.

Round-trip from

$425
(American Airlines)
From Hilton Head Island to Caribbean
Search Deals

Find flight deals from Hilton Head Island to Caribbean

Cheapest flights from Hilton Head Island to Caribbean
Explore the most affordable flight options available from Hilton Head Island to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2025.

This American Airlines deal was found by Cheapflights users on 8/24. 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 9/155:20 pmHHH - SJU
2 stops17h 51mAmerican Airlines
Mon 9/297:05 pmSJU - HHH
2 stops21h 42mAmerican Airlines
Deal found 8/24$425
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/173:02 pmHHH - SJU
1 stop8h 52mAmerican Airlines
Mon 10/275:00 pmSJU - HHH
2 stops19h 15mAmerican Airlines
Deal found 8/24$473
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Fri 10/103:02 pmHHH - GGT
1 stop21h 33mAmerican Airlines
Fri 10/1712:25 pmGGT - HHH
2 stops23h 07mAmerican Airlines
Deal found 8/26$489
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/185:57 pmHHH - SJU
1 stop5h 57mAmerican Airlines
Mon 10/277:10 amSJU - HHH
1 stop7h 22mAmerican Airlines
Deal found 8/24$499
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/173:02 pmHHH - SJU
1 stop8h 52mAmerican Airlines
Sun 10/267:10 amSJU - HHH
1 stop10h 17mAmerican Airlines
Deal found 8/24$514
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/185:57 pmHHH - SJU
1 stop5h 57mAmerican Airlines
Sun 10/267:10 amSJU - HHH
1 stop10h 17mAmerican Airlines
Deal found 8/24$540
This American Airlines deal was found by Cheapflights users on 8/24. 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 10/2812:45 pmHHH - GND
2 stops26h 04mAmerican Airlines
Fri 10/313:54 pmGND - HHH
2 stops22h 38mAmerican Airlines
Deal found 8/24$650
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 10/105:57 pmHHH - POP
2 stops18h 43mAmerican Airlines
Mon 10/133:50 pmPOP - HHH
2 stops18h 56mAmerican Airlines
Deal found 8/25$659
This American Airlines deal was found by Cheapflights users on 8/24. 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 12/87:08 pmHHH - CUR
2 stops20h 26mAmerican Airlines
Wed 12/105:34 pmCUR - HHH
2 stops21h 13mAmerican Airlines
Deal found 8/24$715
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1512:06 pmHHH - SJU
2 stops27h 36mUnited Airlines
Sun 9/281:05 amSJU - HHH
1 stop10h 11mUnited Airlines
Deal found 8/25$824

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island 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 August 26, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Caribbean that are best for you.

Fly from

Hilton Head Island

Fly to

Caribbean

Route

Depart

Return

Price

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

5:20 pm-11:11 am

2 stops17h 51m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:05 pm-4:47 pm

2 stops21h 42m

$425

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Fri 10/17

5:57 pm-11:54 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Mon 10/27

7:10 am-2:32 pm

1 stop7h 22m

$473

Hilton Head IslandGeorgetown

HHH - GGT

HHHGGT

Hilton Head Island

Fri 10/10

3:02 pm-12:35 pm

1 stop21h 33m

Georgetown Exuma Intl

Fri 10/17

12:25 pm-11:32 am

2 stops23h 07m

$489

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 10/18

5:57 pm-11:54 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Mon 10/27

5:00 pm-12:15 pm

2 stops19h 15m

$499

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Fri 10/17

3:02 pm-11:54 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sun 10/26

7:10 am-5:27 pm

1 stop10h 17m

$514

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 10/18

5:57 pm-11:54 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Sun 10/26

7:10 am-5:27 pm

1 stop10h 17m

$540

Hilton Head IslandSt. George's

HHH - GND

HHHGND

Hilton Head Island

Tue 10/28

3:32 pm-2:49 pm

2 stops23h 17m

St. George's Point Saline Intl

Fri 10/31

3:54 pm-10:46 am

2 stops18h 52m

$650

Hilton Head IslandPuerto Plata

HHH - POP

HHHPOP

Hilton Head Island

Fri 10/10

5:57 pm-12:40 pm

2 stops18h 43m

Puerto Plata La Union

Mon 10/13

3:50 pm-10:46 am

2 stops18h 56m

$659

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Mon 12/8

6:21 pm-4:20 pm

2 stops20h 59m

Willemstad Hato Int.

Wed 12/10

5:40 pm-2:16 pm

2 stops21h 36m

$715

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

Best time to book a flight from Hilton Head Island to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Hilton Head Island 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 Hilton Head Island to Caribbean

What is the cheapest month to book a flight from Hilton Head Island to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $254). Flying from Hilton Head Island 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Caribbean. 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 Hilton Head Island to Caribbean?

    Hilton Head Island (HHH), located 3.3 mi from the city center, is the airport you fly out of when you book flights from Hilton Head Island to Caribbean.

  • How long is the flight from Hilton Head Island to Caribbean?

    A quick flight from Hilton Head Island to Caribbean can take about 17h 51m. American Airlines provides one of the quickest options available for as low as $425. There are 1319 mi between Hilton Head Island and Caribbean.

  • What are the most popular routes from Hilton Head Island to Caribbean?

    While some choose either Hilton Head Island - Willemstad Hato Int. or Hilton Head Island - Road Town Beef Island, Hilton Head Island - San Juan Luis Munoz Marin Intl is the most popular route from Hilton Head Island to Caribbean.

  • Can I find deals for flights from Hilton Head Island to Caribbean that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Caribbean?

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

  • Can I find deals for business class flights from Hilton Head Island to Caribbean?

    Yes. Cheapflights offers flight deals from Hilton Head Island 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 Hilton Head Island to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $254). Flying from Hilton Head Island 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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