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$353+ Cheap flights from Hilton Head Island (HHH) 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Round-trip from

$411
(American Airlines)

One-way from

$353
(United Airlines)
From Hilton Head Island to Caribbean
Search Deals
One-way flight from Hilton Head Island to Caribbean
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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 January 8, 2026.

This American Airlines deal was found by Cheapflights users on 1/7. 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.
Wed 2/255:19 pmHHH - SJU
2 stops19h 14mAmerican Airlines
Sat 2/287:01 pmSJU - HHH
2 stops16h 32mAmerican Airlines
Deal found 1/7$411
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Wed 4/296:39 pmHHH - SJU
2 stops14h 34mAmerican Airlines
Mon 5/411:38 amSJU - HHH
1 stop6h 31mAmerican Airlines
Deal found 1/8$515
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/206:20 pmHHH - PUJ
1 stop16h 14mAmerican Airlines
Fri 2/2712:50 pmPUJ - HHH
2 stops22h 43mAmerican Airlines
Deal found 1/6$531
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Wed 4/296:39 pmHHH - SJU
2 stops14h 34mAmerican Airlines
Sun 5/311:38 amSJU - HHH
1 stop6h 31mAmerican Airlines
Deal found 1/8$590
This United Airlines deal was found by Cheapflights users on 1/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:00 pmHHH - SJU
1 stop7h 50mUnited Airlines
Sun 5/31:00 amSJU - HHH
2 stops13h 01mUnited Airlines
Deal found 1/8$603
This United Airlines deal was found by Cheapflights users on 1/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:00 pmHHH - SJU
1 stop7h 50mUnited Airlines
Sat 5/21:00 amSJU - HHH
2 stops13h 01mUnited Airlines
Deal found 1/8$653
This American Airlines deal was found by Cheapflights users on 1/8. 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.
Thu 4/301:08 pmHHH - SJU
1 stop7h 43mAmerican Airlines
Sun 5/311:38 amSJU - HHH
1 stop6h 31mAmerican Airlines
Deal found 1/8$706
This American Airlines deal was found by Cheapflights users on 1/7. 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.
Fri 1/1612:51 pmHHH - PUJ
1 stop24h 00mAmerican Airlines
Mon 1/194:09 pmPUJ - HHH
2 stops21h 11mAmerican Airlines
Deal found 1/7$958
This United Airlines deal was found by Cheapflights users on 1/6. 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.
Sat 3/72:50 pmHHH - MBJ
2 stops46h 15mUnited Airlines
Thu 3/122:20 pmMBJ - HHH
2 stops46h 39mUnited Airlines
Deal found 1/6$1,176
This United Airlines deal was found by Cheapflights users on 1/6. 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.
Thu 6/253:00 pmHHH - PUJ
1 stop23h 27mUnited Airlines
Sun 6/281:50 pmPUJ - HHH
1 stop24h 11mUnited Airlines
Deal found 1/6$1,526

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 January 8, 2026.
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

Wed 2/25

5:19 pm-1:33 pm

2 stops19h 14m

San Juan Luis Munoz Marin Intl

Sat 2/28

7:01 pm-10:33 am

2 stops16h 32m

$411

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Wed 4/29

6:39 pm-9:13 am

2 stops14h 34m

San Juan Luis Munoz Marin Intl

Mon 5/4

11:38 am-6:09 pm

1 stop6h 31m

$515

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Fri 2/20

6:20 pm-11:34 am

1 stop16h 14m

Punta Cana

Fri 2/27

12:50 pm-10:33 am

2 stops22h 43m

$531

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Wed 4/29

6:39 pm-9:13 am

2 stops14h 34m

San Juan Luis Munoz Marin Intl

Sun 5/3

11:38 am-6:09 pm

1 stop6h 31m

$590

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 4/30

4:00 pm-11:50 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Sun 5/3

1:00 am-2:01 pm

2 stops13h 01m

$603

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 4/30

4:00 pm-11:50 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Sat 5/2

1:00 am-2:01 pm

2 stops13h 01m

$653

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 4/30

1:08 pm-8:51 pm

1 stop7h 43m

San Juan Luis Munoz Marin Intl

Sun 5/3

11:38 am-6:09 pm

1 stop6h 31m

$706

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sat 3/7

2:50 pm-1:05 pm

2 stops46h 15m

Montego Bay Sangster Intl

Thu 3/12

2:20 pm-1:59 pm

2 stops46h 39m

$1,176

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Thu 6/25

3:00 pm-2:27 pm

1 stop23h 27m

Punta Cana

Sun 6/28

1:50 pm-2:01 pm

1 stop24h 11m

$1,526

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Fri 5/15

4:00 pm-11:50 pm

1 stop7h 50m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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, December is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $104). Flying from Hilton Head Island to Caribbean in June is currently the most expensive (average of $261). 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 19h 14m. American Airlines provides one of the quickest options available for as low as $411. There are 1319 mi between Hilton Head Island and Caribbean. This flight may include one or multiple stops.

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

    While some choose either Hilton Head Island - Montego Bay Sangster Intl or Hilton Head Island - San Juan Luis Munoz Marin Intl, Hilton Head Island - Punta Cana 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, December is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $104). Flying from Hilton Head Island to Caribbean in June is currently the most expensive (average of $261). 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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