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$298+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Mar 17 — Mar 241
Tue 3/17
Tue 3/24
1 adult, Economy
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Cheap 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 February 15, 2026.

This American Airlines deal was found by Cheapflights users on 2/13. 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.
Sat 4/116:50 pm
HHH
-
SJU
1 stop15h 58m
American Airlines
Fri 4/177:25 am
SJU
-
HHH
1 stop10h 44m
American Airlines
Deal found 2/13$396
This American Airlines deal was found by Cheapflights users on 2/12. 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 2/2711:03 am
HHH
-
SJU
1 stop9h 46m
American Airlines
Tue 3/38:40 am
SJU
-
HHH
1 stop9h 04m
American Airlines
Deal found 2/12$556
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/302:58 pm
HHH
-
PUJ
2 stops20h 08m
American Airlines
Mon 4/64:43 pm
PUJ
-
HHH
2 stops19h 54m
American Airlines
Deal found 2/12$561
This United Airlines deal was found by Cheapflights users on 2/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:11 pm
HHH
-
MBJ
2 stops23h 59m
United Airlines
Tue 4/74:12 pm
MBJ
-
HHH
2 stops21h 04m
United Airlines
Deal found 2/14$685
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Mon 3/306:15 pm
HHH
-
GGT
2 stops19h 11m
American Airlines
Mon 4/611:50 am
GGT
-
HHH
2 stops22h 57m
American Airlines
Deal found 2/13$687
This American Airlines deal was found by Cheapflights users on 2/12. 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 2/136:20 pm
HHH
-
SJU
1 stop16h 20m
American Airlines
Tue 2/178:40 am
SJU
-
HHH
1 stop7h 21m
American Airlines
Deal found 2/12$721
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/52:58 pm
HHH
-
SJU
1 stop5h 51m
American Airlines
Sun 3/87:40 am
SJU
-
HHH
1 stop10h 04m
American Airlines
Deal found 2/12$726
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Tue 6/232:48 pm
HHH
-
SJU
1 stop8h 11m
American Airlines
Sat 6/274:38 pm
SJU
-
HHH
2 stops18h 32m
American Airlines
Deal found 2/13$731
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Thu 6/41:45 pm
HHH
-
MBJ
2 stops26h 25m
United Airlines
Mon 6/812:52 pm
MBJ
-
HHH
2 stops24h 09m
United Airlines
Deal found 2/12$739
This American Airlines deal was found by Cheapflights users on 2/13. 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.
Tue 6/232:48 pm
HHH
-
SJU
1 stop8h 11m
American Airlines
Sat 6/2712:59 am
SJU
-
HHH
1 stop12h 37m
American Airlines
Deal found 2/13$742
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/116:15 pm
HHH
-
PUJ
2 stops16h 51m
American Airlines
Mon 3/164:36 pm
PUJ
-
HHH
1 stop24h 08m
American Airlines
Deal found 2/12$764
This American Airlines deal was found by Cheapflights users on 2/12. 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 3/116:15 pm
HHH
-
PUJ
2 stops16h 51m
American Airlines
Tue 3/174:36 pm
PUJ
-
HHH
2 stops23h 05m
American Airlines
Deal found 2/12$782

Find 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 February 15, 2026.

Round-trip from

$396
(American Airlines)

One-way from

$298
(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 February 15, 2026.
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

Sat 4/11

6:50 pm-10:48 am

1 stop15h 58m

San Juan Luis Munoz Marin Intl

Fri 4/17

7:00 pm-12:37 pm

2 stops17h 37m

$396

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Fri 2/27

11:03 am-9:49 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Tue 3/3

8:00 am-4:44 pm

2 stops9h 44m

$556

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 3/30

2:58 pm-11:06 am

2 stops20h 08m

Punta Cana

Mon 4/6

4:43 pm-12:37 pm

2 stops19h 54m

$561

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 3/31

4:11 pm-3:10 pm

2 stops23h 59m

Montego Bay Sangster Intl

Tue 4/7

4:12 pm-2:16 pm

2 stops21h 04m

$685

Hilton Head IslandGeorgetown

HHH - GGT

HHHGGT

Hilton Head Island

Mon 3/30

6:15 pm-1:26 pm

2 stops19h 11m

Georgetown Exuma Intl

Mon 4/6

11:50 am-10:47 am

2 stops22h 57m

$687

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 3/5

2:58 pm-9:49 pm

1 stop5h 51m

San Juan Luis Munoz Marin Intl

Sun 3/8

7:40 am-5:44 pm

1 stop10h 04m

$726

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Thu 6/4

1:45 pm-3:10 pm

2 stops26h 25m

Montego Bay Sangster Intl

Mon 6/8

12:52 pm-2:01 pm

2 stops24h 09m

$739

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Thu 3/12

4:11 pm-1:20 pm

2 stops21h 09m

Punta Cana

Mon 3/16

4:36 pm-4:44 pm

1 stop24h 08m

$764

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Wed 3/11

6:15 pm-11:06 am

2 stops16h 51m

Punta Cana

Mon 3/16

4:36 pm-4:44 pm

1 stop24h 08m

$764

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Wed 3/11

6:15 pm-11:06 am

2 stops16h 51m

Punta Cana

Tue 3/17

4:36 pm-3:41 pm

2 stops23h 05m

$782

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 25 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $84). Flying from Hilton Head Island to Caribbean in June is currently the most expensive (average of $260). 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 15h 58m. American Airlines provides one of the quickest options available for as low as $396. There are 1319 mi between Hilton Head Island and Caribbean. This flight may include one or multiple stops.

  • 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 - Punta Cana, 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean (average of $84). Flying from Hilton Head Island to Caribbean in June is currently the most expensive (average of $260). 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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