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$360+ Cheap flights from Hilton Head Island (HHH) to Caribbean Islands

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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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Cheap 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 23, 2025.

Round-trip from

$360
(American Airlines)
From Hilton Head Island to Caribbean Islands
Search Deals

Find 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 23, 2025.

This American Airlines deal was found by Cheapflights users on 2/23. 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 4/286:06 pmHHH - SJU
2 stops18h 30mAmerican Airlines
Sat 5/33:35 pmSJU - HHH
2 stops18h 48mAmerican Airlines
Deal found 2/23$360
This Delta deal was found by Cheapflights users on 2/23. 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 4/281:15 pmHHH - SJU
1 stop10h 00mDelta
Sat 5/36:15 amSJU - HHH
1 stop10h 26mDelta
Deal found 2/23$410
This American Airlines deal was found by Cheapflights users on 2/22. 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 9/156:22 pmHHH - MBJ
2 stops17h 33mAmerican Airlines
Mon 9/223:05 pmMBJ - HHH
2 stops18h 36mAmerican Airlines
Deal found 2/22$517
This United Airlines deal was found by Cheapflights users on 2/23. 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.
Mon 4/284:18 pmHHH - SJU
1 stop7h 39mUnited Airlines
Fri 5/21:05 amSJU - HHH
2 stops12h 54mUnited Airlines
Deal found 2/23$744
This American Airlines deal was found by Cheapflights users on 2/23. 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 4/166:06 pmHHH - GGT
2 stops22h 57mAmerican Airlines
Sat 4/191:09 pmGGT - HHH
1 stop25h 11mAmerican Airlines
Deal found 2/23$1,212
This United deal was found by Cheapflights users on 2/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/284:18 pmHHH - SJU
3 stops25h 12mMultiple Airlines
Sat 5/32:00 pmSJU - HHH
2 stops49h 29mMultiple Airlines
Deal found 2/23$2,643

Find flights from Hilton Head Island to Caribbean Islands within your budget

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 23, 2025.

Fly from

Hilton Head Island

Fly to

Caribbean Islands

Route

Depart

Return

Price

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 4/28

6:06 pm-12:36 pm

2 stops18h 30m

San Juan Luis Munoz Marin Intl

Sat 5/3

3:35 pm-10:23 am

2 stops18h 48m

$360

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 4/28

1:15 pm-11:15 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Sat 5/3

6:15 am-4:41 pm

1 stop10h 26m

$410

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 4/28

4:18 pm-11:57 pm

1 stop7h 39m

San Juan Luis Munoz Marin Intl

Fri 5/2

1:05 am-1:59 pm

2 stops12h 54m

$744

Hilton Head IslandGeorgetown

HHH - GGT

HHHGGT

Hilton Head Island

Wed 4/16

6:06 pm-5:03 pm

2 stops22h 57m

Georgetown Exuma Intl

Sat 4/19

1:09 pm-2:20 pm

1 stop25h 11m

$1,212

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 4/28

4:18 pm-5:30 pm

3 stops25h 12m

San Juan Luis Munoz Marin Intl

Sat 5/3

2:00 pm-3:29 pm

2 stops49h 29m

$2,643

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

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.

Travel insights for flights from Hilton Head Island to Caribbean Islands

Get recent, data-driven insights about flights from Hilton Head Island to Caribbean Islands including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Hilton Head Island to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean Islands (average of $254). Flying from Hilton Head Island to Caribbean Islands in March is currently the most expensive (average of $363). 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 Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 23, 2025.
Delta
8.0
Very good
8,191 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Entertainment

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
8,191 reviews
Delta
8.0
Very good
8,191 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Entertainment

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.

United Airlines
7.4
Good
8,746 reviews
Delta
8.0
Very good
8,191 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Entertainment

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
8,191 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Comfort

8.0

Crew

8.5

Entertainment

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 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.

  • 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 - Montego Bay Sangster Intl, Hilton Head Island - San Juan Luis Munoz Marin Intl and Hilton Head Island - Georgetown Exuma 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, September is the cheapest month in which you can book a flight from Hilton Head Island to Caribbean Islands (average of $254). Flying from Hilton Head Island to Caribbean Islands in March is currently the most expensive (average of $363). 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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