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$365+ Cheap flights from Hilton Head Island (HHH) to Caribbean

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$365
(American Airlines)
From Hilton Head Island to Caribbean
Search Deals

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 septiembre 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
jue. 12/46:52 pmHHH - SJU
2 stops16h 07mAmerican Airlines
lun. 12/86:42 pmSJU - HHH
2 stops21h 15mAmerican Airlines
Deal found 9/15$365
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/143:32 pmHHH - SJU
1 stop6h 38mAmerican Airlines
mié. 10/227:45 amSJU - HHH
1 stop9h 06mAmerican Airlines
Deal found 9/14$515
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/143:32 pmHHH - SJU
1 stop6h 38mAmerican Airlines
mar. 10/217:45 amSJU - HHH
1 stop9h 06mAmerican Airlines
Deal found 9/14$535
This American Airlines deal was found by Cheapflights users on 9/14. 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.
mar. 10/143:32 pmHHH - SJU
1 stop6h 38mAmerican Airlines
lun. 10/207:10 amSJU - HHH
1 stop7h 22mAmerican Airlines
Deal found 9/14$575
This American Airlines deal was found by Cheapflights users on 9/14. 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.
lun. 9/153:26 pmHHH - SJU
2 stops8h 11mAmerican Airlines
lun. 9/291:37 pmSJU - HHH
2 stops22h 40mAmerican Airlines
Deal found 9/14$605
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/2812:45 pmHHH - GND
2 stops26h 04mAmerican Airlines
vie. 10/313:54 pmGND - HHH
2 stops19h 38mAmerican Airlines
Deal found 9/13$710
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/83:27 pmHHH - CUR
2 stops22h 17mAmerican Airlines
mié. 12/103:44 pmCUR - HHH
2 stops20h 15mAmerican Airlines
Deal found 9/13$715
This American Airlines deal was found by Cheapflights users on 9/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/83:27 pmHHH - SKB
2 stops21h 53mAmerican Airlines
jue. 12/113:21 pmSKB - HHH
2 stops20h 38mAmerican Airlines
Deal found 9/13$758
This American Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 9/263:26 pmHHH - MBJ
2 stops21h 39mAmerican Airlines
dom. 9/281:56 pmMBJ - HHH
1 stop24h 00mAmerican Airlines
Deal found 9/14$786
This Trip.com deal was found by Cheapflights users on 9/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/111:57 amHHH - CUR
2 stops48h 20mUnited Airlines
dom. 10/51:16 pmCUR - HHH
2 stops46h 00mUnited Airlines
Deal found 9/15$984
This United Airlines deal was found by Cheapflights users on 9/15. 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.
vie. 9/1912:06 pmHHH - SJU
2 stops27h 36mUnited Airlines
dom. 9/211:05 amSJU - HHH
1 stop10h 20mUnited Airlines
Deal found 9/15$1,029
This Delta deal was found by Cheapflights users on 9/14. 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.
vie. 9/264:05 pmHHH - MBJ
2 stops20h 55mDelta
dom. 9/282:35 pmMBJ - HHH
2 stops19h 55mDelta
Deal found 9/14$1,344

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 septiembre 15, 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

jue. 12/4

6:52 pm-11:59 am

2 stops16h 07m

San Juan Luis Munoz Marin Intl

lun. 12/8

6:42 pm-2:57 pm

2 stops21h 15m

$365

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

mar. 10/14

3:32 pm-10:10 pm

1 stop6h 38m

San Juan Luis Munoz Marin Intl

mié. 10/22

7:00 am-4:51 pm

2 stops9h 51m

$515

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

mar. 10/14

3:32 pm-10:10 pm

1 stop6h 38m

San Juan Luis Munoz Marin Intl

mar. 10/21

7:00 am-4:51 pm

2 stops9h 51m

$515

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

mié. 2/4

6:14 pm-10:15 am

1 stop16h 01m

Montego Bay Sangster Intl

dom. 2/8

11:50 am-5:34 pm

1 stop5h 44m

$586

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

mar. 3/10

11:04 am-3:05 pm

1 stop5h 01m

Montego Bay Sangster Intl

mié. 3/11

5:00 pm-5:34 pm

2 stops23h 34m

$645

Hilton Head IslandSt. George's

HHH - GND

HHHGND

Hilton Head Island

mar. 10/28

12:45 pm-2:49 pm

2 stops26h 04m

St. George's Point Saline Intl

vie. 10/31

3:54 pm-11:32 am

2 stops19h 38m

$710

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

lun. 12/8

3:27 pm-2:44 pm

2 stops22h 17m

Willemstad Hato Int.

mié. 12/10

3:44 pm-10:59 am

2 stops20h 15m

$715

Hilton Head IslandBasseterre

HHH - SKB

HHHSKB

Hilton Head Island

lun. 12/8

3:27 pm-2:20 pm

2 stops21h 53m

Basseterre Robert Bradshaw Intl

jue. 12/11

3:21 pm-10:59 am

2 stops20h 38m

$758

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

vie. 9/26

3:26 pm-12:05 pm

2 stops21h 39m

Montego Bay Sangster Intl

dom. 9/28

1:56 pm-2:56 pm

1 stop24h 00m

$786

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

vie. 9/26

4:05 pm-12:00 pm

2 stops20h 55m

Montego Bay Sangster Intl

dom. 9/28

2:35 pm-11:30 am

2 stops19h 55m

$1,344

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 11 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, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $254). Flying from Hilton Head Island to Caribbean 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. 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 16h 07m. American Airlines provides one of the quickest options available for as low as $365. 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 - Montego Bay Sangster Intl or Hilton Head Island - Willemstad Hato Int., 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, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $254). Flying from Hilton Head Island to Caribbean 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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