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$391+ 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
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Round-trip from

$391
(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 April 29, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 9/154:07 pmHHH - SJU
2 stops19h 08mAmerican Airlines
Mon 9/293:58 pmSJU - HHH
2 stops18h 14mAmerican Airlines
Deal found 4/29$391
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/146:20 pmHHH - MHH
2 stops16h 55mAmerican Airlines
Wed 6/252:08 pmMHH - HHH
2 stops21h 07mAmerican Airlines
Deal found 4/29$614
This Delta deal was found by Cheapflights users on 4/29. 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 9/1512:00 pmHHH - SJU
1 stop10h 08mDelta
Mon 9/297:30 amSJU - HHH
1 stop7h 50mDelta
Deal found 4/29$665
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/206:06 pmHHH - EIS
2 stops19h 52mAmerican Airlines
Thu 7/244:50 pmEIS - HHH
2 stops18h 36mAmerican Airlines
Deal found 4/29$756
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/135:50 pmHHH - PUJ
2 stops18h 45mAmerican Airlines
Fri 6/203:10 pmPUJ - HHH
2 stops19h 23mAmerican Airlines
Deal found 4/29$758

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 April 29, 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

4:07 pm-11:15 am

2 stops19h 08m

San Juan Luis Munoz Marin Intl

Mon 9/29

3:58 pm-10:12 am

2 stops18h 14m

$391

Hilton Head IslandMarsh Harbour

HHH - MHH

HHHMHH

Hilton Head Island

Sat 6/14

6:20 pm-11:15 am

2 stops16h 55m

Marsh Harbour

Wed 6/25

2:08 pm-11:15 am

2 stops21h 07m

$614

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

12:00 pm-10:08 pm

1 stop10h 08m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:30 am-3:20 pm

1 stop7h 50m

$665

Hilton Head IslandRoad Town

HHH - EIS

HHHEIS

Hilton Head Island

Sun 7/20

6:06 pm-1:58 pm

2 stops19h 52m

Road Town Beef Island

Thu 7/24

4:50 pm-11:26 am

2 stops18h 36m

$756

Hilton Head IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Fri 6/13

5:50 pm-12:35 pm

2 stops18h 45m

Punta Cana

Fri 6/20

3:10 pm-10:33 am

2 stops19h 23m

$758

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 December is currently the most expensive (average of $336). 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 29, 2025.
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Overall

8.0

Food

7.3

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 - Puerto Plata La Union, 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 December is currently the most expensive (average of $336). 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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