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Caribbean Islands

$283+ Cheap flights from Hilton Head Island (HHH) to Caribbean Islands

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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
1 adult, Economy
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Cheap 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 February 22, 2026.

This American Airlines deal was found by Cheapflights users on 2/21. 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 5/45:04 pm
HHH
-
SJU
2 stops17h 49m
American Airlines
Thu 5/73:44 pm
SJU
-
HHH
2 stops18h 48m
American Airlines
Deal found 2/21$396
This Delta deal was found by Cheapflights users on 2/21. 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.
Mon 4/1312:08 pm
HHH
-
SJU
1 stop8h 16m
Delta
Sat 4/187:30 am
SJU
-
HHH
1 stop7h 50m
Delta
Deal found 2/21$421
This Delta deal was found by Cheapflights users on 2/21. 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.
Mon 4/1312:08 pm
HHH
-
SJU
1 stop8h 16m
Delta
Fri 4/177:30 am
SJU
-
HHH
1 stop7h 50m
Delta
Deal found 2/21$466
This Delta deal was found by Cheapflights users on 2/21. 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.
Mon 4/1312:08 pm
HHH
-
SJU
1 stop8h 16m
Delta
Wed 4/156:15 am
SJU
-
HHH
1 stop9h 05m
Delta
Deal found 2/21$476
This American Airlines deal was found by Cheapflights users on 2/21. 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 4/142:54 pm
HHH
-
SJU
2 stops19h 59m
American Airlines
Thu 4/163:44 pm
SJU
-
HHH
2 stops18h 48m
American Airlines
Deal found 2/21$506
This American Airlines deal was found by Cheapflights users on 2/21. 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 4/82:58 pm
HHH
-
SJU
1 stop5h 53m
American Airlines
Fri 4/173:44 pm
SJU
-
HHH
2 stops18h 48m
American Airlines
Deal found 2/21$526
This Delta deal was found by Cheapflights users on 2/21. 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.
Mon 4/1312:08 pm
HHH
-
SJU
1 stop8h 16m
Delta
Thu 4/167:30 am
SJU
-
HHH
1 stop7h 50m
Delta
Deal found 2/21$527
This American Airlines deal was found by Cheapflights users on 2/21. 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 4/142:54 pm
HHH
-
SJU
1 stop5h 57m
American Airlines
Sat 4/186:02 pm
SJU
-
HHH
2 stops16h 30m
American Airlines
Deal found 2/21$531
This Delta deal was found by Cheapflights users on 2/21. 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.
Tue 4/1412:08 pm
HHH
-
SJU
1 stop8h 16m
Delta
Thu 4/166:15 am
SJU
-
HHH
1 stop9h 05m
Delta
Deal found 2/21$536
This American Airlines deal was found by Cheapflights users on 2/21. 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 4/86:39 pm
HHH
-
SJU
1 stop16h 09m
American Airlines
Sat 4/186:02 pm
SJU
-
HHH
2 stops16h 30m
American Airlines
Deal found 2/21$551
This American Airlines deal was found by Cheapflights users on 2/21. 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
Thu 4/163:44 pm
SJU
-
HHH
2 stops18h 48m
American Airlines
Deal found 2/21$566
This United Airlines deal was found by Cheapflights users on 2/21. 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 4/143:05 pm
HHH
-
MBJ
2 stops49h 05m
United Airlines
Mon 4/204:12 pm
MBJ
-
HHH
2 stops21h 04m
United Airlines
Deal found 2/21$578

Find 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 February 22, 2026.

Round-trip from

$396
(American Airlines)

One-way from

$283
(American Airlines)
From Hilton Head Island to Caribbean Islands
Search Deals
One-way flight from Hilton Head Island to Caribbean Islands
Search Deals

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 February 22, 2026.
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

Mon 5/4

2:58 pm-8:51 pm

1 stop5h 53m

San Juan Luis Munoz Marin Intl

Thu 5/7

7:25 am-4:34 pm

1 stop9h 09m

$416

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/14

12:08 pm-8:24 pm

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Sat 4/18

7:30 am-3:20 pm

1 stop7h 50m

$421

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Wed 4/15

3:05 pm-3:10 pm

2 stops25h 05m

Montego Bay Sangster Intl

Mon 4/20

4:12 pm-2:16 pm

2 stops21h 04m

$578

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Tue 4/14

3:05 pm-3:10 pm

2 stops49h 05m

Montego Bay Sangster Intl

Mon 4/20

4:12 pm-2:16 pm

2 stops21h 04m

$578

Hilton Head IslandGeorgetown

HHH - GGT

HHHGGT

Hilton Head Island

Sun 4/12

6:39 pm-11:21 am

2 stops16h 42m

Georgetown Exuma Intl

Tue 4/21

2:50 pm-10:32 am

2 stops19h 42m

$585

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 4/9

2:58 pm-8:51 pm

1 stop5h 53m

San Juan Luis Munoz Marin Intl

Sun 4/12

7:00 pm-2:26 pm

2 stops19h 26m

$762

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Mon 6/8

3:05 pm-12:40 pm

2 stops21h 35m

Punta Cana

Thu 6/11

4:00 pm-2:21 pm

2 stops22h 21m

$881

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sat 6/13

1:45 pm-1:30 pm

2 stops24h 45m

Montego Bay Sangster Intl

Sat 6/20

4:12 pm-12:52 pm

2 stops19h 40m

$908

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 4/6

3:05 pm-2:44 pm

1 stop23h 39m

San Juan Luis Munoz Marin Intl

Fri 4/10

7:40 am-2:16 pm

1 stop30h 36m

$1,059

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 4/6

3:05 pm-2:44 pm

1 stop23h 39m

San Juan Luis Munoz Marin Intl

Sun 4/12

7:40 am-2:16 pm

1 stop30h 36m

$1,180

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 13 results
1
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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, January is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean Islands (average of $84). Flying from Hilton Head Island to Caribbean Islands 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 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 5h 53m. American Airlines provides one of the quickest options available for as low as $416. Hilton Head Island and Caribbean Islands are separated by a distance of 1319 mi. This flight may include one or multiple stops.

  • 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 - Road Town Beef Island, Hilton Head Island - Montego Bay Sangster Intl and Hilton Head Island - San Juan Luis Munoz Marin 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean Islands (average of $84). Flying from Hilton Head Island to Caribbean Islands 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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