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Caribbean Islands

$390+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

Round-trip from

$390
(American Airlines)
From Hilton Head Island to Caribbean Islands
Search Deals

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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 12/46:52 pmHHH - SJU
2 stops16h 07mAmerican Airlines
Mon 12/86:42 pmSJU - HHH
2 stops21h 15mAmerican Airlines
Deal found 10/27$425
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.
Mon 12/87:08 pmHHH - CUR
2 stops18h 36mAmerican Airlines
Wed 12/104:32 pmCUR - HHH
2 stops19h 27mAmerican Airlines
Deal found 10/26$715
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 12/87:08 pmHHH - EIS
2 stops18h 48mAmerican Airlines
Wed 12/104:45 pmEIS - HHH
2 stops26h 36mAmerican Airlines
Deal found 10/25$993
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 12/812:52 pmHHH - SKB
2 stops24h 35mAmerican Airlines
Thu 12/113:27 pmSKB - HHH
2 stops28h 06mAmerican Airlines
Deal found 10/25$1,203

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 October 28, 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

Fri 2/6

12:51 pm-10:48 am

2 stops20h 57m

San Juan Luis Munoz Marin Intl

Thu 2/12

7:00 pm-10:33 am

2 stops16h 33m

$390

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 12/4

2:17 pm-10:09 am

2 stops18h 52m

San Juan Luis Munoz Marin Intl

Mon 12/8

8:20 am-6:33 pm

1 stop11h 13m

$425

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/7

11:02 am-11:00 am

2 stops23h 58m

San Juan Luis Munoz Marin Intl

Wed 4/8

6:55 pm-5:36 pm

2 stops22h 41m

$473

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 4/6

6:25 pm-12:40 pm

2 stops18h 15m

Punta Cana

Wed 4/8

12:50 pm-10:14 am

2 stops21h 24m

$582

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

3:29 pm-10:10 am

2 stops18h 41m

Montego Bay Sangster Intl

Sun 2/8

4:16 pm-12:20 pm

2 stops20h 04m

$591

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 3/24

6:25 pm-1:00 pm

2 stops19h 35m

Montego Bay Sangster Intl

Thu 3/26

5:00 pm-10:24 am

2 stops16h 24m

$646

Hilton Head IslandPuerto Plata

HHH - POP

HHHPOP

Hilton Head Island

Mon 3/30

4:10 pm-2:15 pm

2 stops22h 05m

Puerto Plata La Union

Thu 4/2

3:35 pm-5:34 pm

2 stops25h 59m

$703

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Mon 12/8

7:08 pm-2:44 pm

2 stops18h 36m

Willemstad Hato Int.

Wed 12/10

4:32 pm-10:59 am

2 stops19h 27m

$715

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 4/6

3:00 pm-12:40 pm

2 stops21h 40m

Punta Cana

Wed 4/8

4:35 pm-1:52 pm

3 stops21h 17m

$965

Hilton Head IslandRoad Town

HHH - EIS

HHHEIS

Hilton Head Island

Mon 12/8

7:08 pm-2:56 pm

2 stops18h 48m

Road Town Beef Island

Wed 12/10

4:45 pm-6:21 pm

2 stops26h 36m

$993

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 11 results
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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, May is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean Islands (average of $155). Flying from Hilton Head Island to Caribbean Islands in December is currently the most expensive (average of $325). 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.

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

    A quick flight from Hilton Head Island to Caribbean Islands can take about 20h 57m. American Airlines provides one of the quickest options available for as low as $390. Hilton Head Island and Caribbean Islands are separated by a distance of 1319 mi.

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

    The most popular flight routes from Hilton Head Island to Caribbean Islands are Hilton Head Island - San Juan Luis Munoz Marin Intl, Hilton Head Island - Punta Cana and Hilton Head Island - Montego Bay Sangster Intl.

  • 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, May is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean Islands (average of $155). Flying from Hilton Head Island to Caribbean Islands in December is currently the most expensive (average of $325). 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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