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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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/3. 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 9/155:20 pmHHH - SJU
2 stops17h 51mAmerican Airlines
Mon 9/297:05 pmSJU - HHH
2 stops21h 42mAmerican Airlines
Deal found 7/3$365
This Delta deal was found by Cheapflights users on 7/3. 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 9/1512:10 pmHHH - SJU
1 stop9h 50mDelta
Mon 9/297:30 amSJU - HHH
1 stop7h 52mDelta
Deal found 7/3$490
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Sun 9/76:20 pmHHH - MBJ
2 stops18h 45mAmerican Airlines
Sat 9/133:36 pmMBJ - HHH
2 stops18h 54mAmerican Airlines
Deal found 7/2$560
This American Airlines deal was found by Cheapflights users on 7/2. 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 10/285:25 pmHHH - GND
2 stops21h 24mAmerican Airlines
Fri 10/313:54 pmGND - HHH
2 stops19h 38mAmerican Airlines
Deal found 7/2$630
This American Airlines deal was found by Cheapflights users on 7/2. 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 12/86:21 pmHHH - CUR
2 stops20h 59mAmerican Airlines
Wed 12/105:40 pmCUR - HHH
2 stops24h 50mAmerican Airlines
Deal found 7/2$695
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Fri 7/412:02 pmHHH - SJU
2 stops17h 28mUnited Airlines
Sun 7/61:10 amSJU - HHH
1 stop10h 07mUnited Airlines
Deal found 7/1$761

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 July 3, 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

Mon 9/15

5:20 pm-11:11 am

2 stops17h 51m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:05 pm-4:47 pm

2 stops21h 42m

$365

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

12:10 pm-10:00 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:30 am-3:22 pm

1 stop7h 52m

$490

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Sun 9/7

6:20 pm-12:05 pm

2 stops18h 45m

Montego Bay Sangster Intl

Sat 9/13

3:36 pm-11:30 am

2 stops18h 54m

$560

Hilton Head IslandSt. George's

HHH - GND

HHHGND

Hilton Head Island

Tue 10/28

5:25 pm-2:49 pm

2 stops21h 24m

St. George's Point Saline Intl

Fri 10/31

3:54 pm-11:32 am

2 stops19h 38m

$630

Hilton Head IslandWillemstad

HHH - CUR

HHHCUR

Hilton Head Island

Mon 12/8

6:21 pm-4:20 pm

2 stops20h 59m

Willemstad Hato Int.

Wed 12/10

5:40 pm-5:30 pm

2 stops24h 50m

$695

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

12:06 pm-3:42 pm

2 stops27h 36m

San Juan Luis Munoz Marin Intl

Sun 9/28

1:05 am-11:22 am

1 stop10h 17m

$909

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sun 8/3

12:05 pm-10:23 pm

1 stop10h 18m

$689

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Sun 8/3

12:02 pm-8:38 pm

2 stops32h 36m

$1,011

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated July 3, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Hilton Head Island to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,861 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,982 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 - Christiansted Henry Rohlsen, 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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