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$317+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/5. 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 12/42:17 pmHHH - SJU
1 stop6h 48mAmerican Airlines
Mon 12/88:20 amSJU - HHH
1 stop7h 37mAmerican Airlines
Deal found 11/5$465
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Tue 12/97:08 pmHHH - SJU
2 stops14h 01mAmerican Airlines
Sun 12/146:42 pmSJU - HHH
2 stops21h 15mAmerican Airlines
Deal found 11/6$505
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/105:34 pmCUR - HHH
2 stops19h 17mAmerican Airlines
Deal found 11/5$715
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/206:13 pmHHH - PUJ
1 stop16h 15mAmerican Airlines
Tue 12/2312:29 pmPUJ - HHH
2 stops23h 15mAmerican Airlines
Deal found 11/5$717
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/206:13 pmHHH - PUJ
2 stops20h 51mAmerican Airlines
Wed 12/2412:29 pmPUJ - HHH
2 stops23h 15mAmerican Airlines
Deal found 11/5$834
This American Airlines deal was found by Cheapflights users on 11/6. 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 11/216:40 pmHHH - SJU
2 stops14h 30mAmerican Airlines
Tue 11/256:00 amSJU - HHH
2 stops9h 19mAmerican Airlines
Deal found 11/6$840
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/186:13 pmHHH - PUJ
2 stops22h 36mAmerican Airlines
Wed 12/245:23 pmPUJ - HHH
2 stops18h 21mAmerican Airlines
Deal found 11/5$859
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/206:13 pmHHH - PUJ
2 stops22h 36mAmerican Airlines
Thu 12/253:39 pmPUJ - HHH
2 stops20h 05mAmerican Airlines
Deal found 11/5$867
This American Airlines deal was found by Cheapflights users on 11/5. 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 12/186:13 pmHHH - PUJ
2 stops20h 51mAmerican Airlines
Thu 12/251:15 pmPUJ - HHH
2 stops22h 29mAmerican Airlines
Deal found 11/5$892
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 12/46:52 pmHHH - EIS
2 stops20h 09mAmerican Airlines
Fri 12/193:55 pmEIS - HHH
2 stops19h 49mAmerican Airlines
Deal found 11/6$1,128

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 November 6, 2025.

Round-trip from

$465
(American Airlines)

One-way from

$317
(American Airlines)
From Hilton Head Island to Caribbean
Search Deals
One-way flight from Hilton Head Island to Caribbean
Search Deals

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 November 6, 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

Thu 12/4

2:17 pm-10:05 pm

1 stop6h 48m

San Juan Luis Munoz Marin Intl

Mon 12/8

8:20 am-2:57 pm

1 stop7h 37m

$465

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 12/9

3:27 pm-10:09 am

2 stops17h 42m

San Juan Luis Munoz Marin Intl

Sun 12/14

8:18 am-6:21 pm

1 stop11h 03m

$465

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/7

6:07 pm-12:35 pm

2 stops18h 28m

San Juan Luis Munoz Marin Intl

Wed 4/8

3:50 pm-10:14 am

2 stops18h 24m

$473

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 2/4

12:51 pm-10:10 am

2 stops21h 19m

Montego Bay Sangster Intl

Sun 2/8

11:10 am-12:20 pm

2 stops25h 10m

$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-5:34 pm

2 stops23h 34m

$646

Hilton Head IslandPuerto Plata

HHH - POP

HHHPOP

Hilton Head Island

Mon 3/30

6:25 pm-2:15 pm

2 stops19h 50m

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

5:34 pm-6:21 pm

2 stops25h 47m

$715

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Sat 12/20

6:13 pm-11:28 am

1 stop16h 15m

Punta Cana

Wed 12/24

1:15 pm-10:44 am

2 stops22h 29m

$717

Hilton Head IslandSt. George's

HHH - GND

HHHGND

Hilton Head Island

Mon 5/4

4:05 pm-1:45 pm

2 stops21h 40m

St. George's Point Saline Intl

Wed 5/6

3:30 pm-10:14 am

2 stops18h 44m

$731

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Sat 12/20

6:13 pm-5:49 pm

2 stops22h 36m

Punta Cana

Tue 12/23

5:23 pm-10:44 am

2 stops18h 21m

$834

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 23 results
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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, May is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $155). Flying from Hilton Head Island to Caribbean in June is currently the most expensive (average of $284). 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 6h 48m. American Airlines provides one of the quickest options available for as low as $465. 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 - Punta Cana or Hilton Head Island - Montego Bay Sangster Intl, 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, May is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $155). Flying from Hilton Head Island to Caribbean in June is currently the most expensive (average of $284). 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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