Caribbean Islands

$405+ Cheap flights from Hilton Head Island (HHH) 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Aug 21 — Aug 281
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Cheap flight deals from Hilton Head Island to Caribbean Islands

Keep the following information in mind while searching for Hilton Head Island to Caribbean Islands flight deals. Data was last updated August 16, 2025.

Round-trip from

$405
(American Airlines)
From Hilton Head Island to Caribbean Islands

Find flight deals from Hilton Head Island to Caribbean Islands

Cheapest flights from Hilton Head Island to Caribbean Islands
Explore the most affordable flight options available from Hilton Head Island to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2025.

This American Airlines deal was found by Cheapflights users on 8/15. 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 stops21h 33mAmerican Airlines
Mon 9/297:05 pmSJU - HHH
2 stops21h 42mAmerican Airlines
Deal found 8/15$405
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1512:14 pmHHH - SJU
1 stop9h 46mDelta
Mon 9/297:30 amSJU - HHH
1 stop7h 55mDelta
Deal found 8/14$588
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/285:21 pmHHH - GND
2 stops21h 28mAmerican Airlines
Fri 10/313:54 pmGND - HHH
2 stops19h 38mAmerican Airlines
Deal found 8/14$650
This American Airlines deal was found by Cheapflights users on 8/15. 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 12/84:09 pmHHH - CUR
2 stops23h 11mAmerican Airlines
Wed 12/105:40 pmCUR - HHH
2 stops21h 36mAmerican Airlines
Deal found 8/15$715
This American Airlines deal was found by Cheapflights users on 8/15. 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 12/86:21 pmHHH - SKB
2 stops18h 54mAmerican Airlines
Thu 12/113:30 pmSKB - HHH
2 stops27h 00mAmerican Airlines
Deal found 8/15$748
This United Airlines deal was found by Cheapflights users on 8/15. 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 stops32h 32mUnited Airlines
Sun 9/281:05 amSJU - HHH
1 stop10h 11mUnited Airlines
Deal found 8/15$782
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2012:02 pmHHH - SJU
1 stop11h 55mUnited Airlines
Tue 8/261:05 amSJU - HHH
1 stop10h 16mUnited Airlines
Deal found 8/13$877
This United Airlines deal was found by Cheapflights users on 8/15. 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 8/3012:02 pmHHH - SJU
2 stops24h 32mUnited Airlines
Tue 9/21:05 amSJU - HHH
1 stop10h 20mUnited Airlines
Deal found 8/15$932
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/912:17 pmHHH - SJU
1 stop9h 42mDelta
Mon 10/137:15 amSJU - HHH
1 stop8h 15mDelta
Deal found 8/14$1,022

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island 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 August 16, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Caribbean Islands that are best for you.

Fly from

Hilton Head Island

Fly to

Caribbean Islands

Route

Depart

Return

Price

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

5:20 pm-2:53 pm

2 stops21h 33m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:05 pm-2:56 pm

2 stops19h 51m

$405

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

12:14 pm-10:00 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:30 am-3:25 pm

1 stop7h 55m

$588

Hilton Head IslandSt. George's

HHH - GND

HHHGND

Hilton Head Island

Tue 10/28

5:21 pm-2:49 pm

2 stops21h 28m

St. George's Point Saline Intl

Fri 10/31

3:54 pm-11:32 am

2 stops19h 38m

$650

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Mon 12/8

4:09 pm-2:15 pm

2 stops21h 06m

Willemstad Hato Int.

Wed 12/10

5:40 pm-5:30 pm

2 stops24h 50m

$715

Hilton Head IslandBasseterre

HHH - SKB

HHHSKB

Hilton Head Island

Mon 12/8

6:21 pm-2:15 pm

2 stops18h 54m

Basseterre Robert Bradshaw Intl

Thu 12/11

3:30 pm-5:30 pm

2 stops27h 00m

$748

Hilton Head IslandRoad Town

HHH - EIS

HHHEIS

Hilton Head Island

Fri 1/23

6:14 pm-1:49 pm

2 stops18h 35m

Road Town Beef Island

Mon 2/9

3:35 pm-2:18 pm

2 stops23h 43m

$777

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

12:06 pm-8:38 pm

2 stops32h 32m

San Juan Luis Munoz Marin Intl

Sun 9/28

1:05 am-11:16 am

1 stop10h 11m

$782

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 8/30

12:02 pm-12:34 pm

2 stops24h 32m

San Juan Luis Munoz Marin Intl

Tue 9/2

1:05 am-11:25 am

1 stop10h 20m

$932

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sat 8/30

12:02 pm-12:34 pm

2 stops24h 32m

$590

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

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

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

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

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

    Located just 3.3 mi from the city center, Hilton Head Island (HHH) is the airport most travelers will use when flying to Caribbean Islands from Hilton Head Island.

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

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

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

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

    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 Islands.

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

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

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