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$333+ 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 11/22. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
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 October 16, 2025.

This American Airlines deal was found by Cheapflights users on 10/14. 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.
Sat 11/296:40 pmHHH - MBJ
1 stop15h 28mAmerican Airlines
Sat 12/611:12 amMBJ - HHH
1 stop7h 00mAmerican Airlines
Deal found 10/14$632
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Sat 11/222:51 pmHHH - SJU
2 stops18h 19mAmerican Airlines
Sat 11/298:00 amSJU - HHH
1 stop11h 09mAmerican Airlines
Deal found 10/15$655
This American Airlines deal was found by Cheapflights users on 10/15. 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 12/811:30 amHHH - CUR
2 stops26h 14mAmerican Airlines
Wed 12/103:44 pmCUR - HHH
2 stops20h 15mAmerican Airlines
Deal found 10/15$715
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 12/252:46 pmHHH - MBJ
1 stop25h 36mAmerican Airlines
Mon 12/2911:27 amMBJ - HHH
1 stop6h 16mAmerican Airlines
Deal found 10/15$724
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 12/252:46 pmHHH - MBJ
1 stop25h 36mAmerican Airlines
Sun 12/2811:27 amMBJ - HHH
1 stop6h 16mAmerican Airlines
Deal found 10/15$729
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Thu 12/252:46 pmHHH - MBJ
1 stop25h 36mAmerican Airlines
Sat 12/276:00 pmMBJ - HHH
2 stops23h 43mAmerican Airlines
Deal found 10/15$753
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 12/242:46 pmHHH - MBJ
2 stops22h 06mAmerican Airlines
Mon 12/2911:27 amMBJ - HHH
1 stop6h 16mAmerican Airlines
Deal found 10/15$779
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 12/242:46 pmHHH - MBJ
2 stops22h 06mAmerican Airlines
Sun 12/282:23 pmMBJ - HHH
2 stops20h 21mAmerican Airlines
Deal found 10/15$784
This American Airlines deal was found by Cheapflights users on 10/15. 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.
Wed 12/242:46 pmHHH - MBJ
2 stops22h 06mAmerican Airlines
Sat 12/2711:49 amMBJ - HHH
1 stop5h 54mAmerican Airlines
Deal found 10/15$804
This American Airlines deal was found by Cheapflights users on 10/14. 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 10/283:32 pmHHH - GND
2 stops23h 17mAmerican Airlines
Fri 10/313:54 pmGND - HHH
2 stops18h 52mAmerican Airlines
Deal found 10/14$863
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 12/87:08 pmHHH - EIS
2 stops18h 48mAmerican Airlines
Wed 12/105:48 pmEIS - HHH
2 stops19h 03mAmerican Airlines
Deal found 10/14$893
This American Airlines deal was found by Cheapflights users on 10/16. 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 12/296:13 pmHHH - EIS
2 stops27h 01mAmerican Airlines
Thu 1/88:00 amEIS - HHH
2 stops29h 20mAmerican Airlines
Deal found 10/16$915

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 October 16, 2025.

Round-trip from

$442
(American Airlines)
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 October 16, 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

Sun 3/1

6:15 pm-1:35 pm

2 stops18h 20m

San Juan Luis Munoz Marin Intl

Thu 3/5

9:30 am-5:31 pm

1 stop9h 01m

$442

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

6:55 pm-5:36 pm

2 stops22h 41m

$473

Hilton Head IslandMarsh Harbour

HHH - MHH

HHHMHH

Hilton Head Island

Mon 3/30

11:04 am-11:10 am

2 stops24h 06m

Marsh Harbour

Wed 4/1

12:50 pm-10:24 am

2 stops21h 34m

$559

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 4/6

4:10 pm-2:40 pm

2 stops22h 30m

Punta Cana

Wed 4/8

4:45 pm-10:14 am

2 stops17h 29m

$582

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

4:16 pm-12:20 pm

2 stops20h 04m

$591

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sat 11/29

6:40 pm-10:08 am

1 stop15h 28m

Montego Bay Sangster Intl

Sat 12/6

11:12 am-6:12 pm

1 stop7h 00m

$632

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 3/24

4:10 pm-9:05 am

2 stops17h 55m

Montego Bay Sangster Intl

Thu 3/26

10:55 am-10:24 am

2 stops22h 29m

$646

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 3/10

11:04 am-3:05 pm

1 stop5h 01m

Montego Bay Sangster Intl

Wed 3/11

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-4:34 pm

2 stops20h 26m

Willemstad Hato Int.

Wed 12/10

5:34 pm-11:51 am

2 stops19h 17m

$715

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 27 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 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. 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 18h 20m. American Airlines provides one of the quickest options available for as low as $442. 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 - San Juan Luis Munoz Marin Intl or Hilton Head Island - Willemstad Hato Int., Hilton Head Island - Montego Bay Sangster 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 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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