Caribbean

$491+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Apr 5 — Apr 121
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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 March 31, 2025.

Round-trip from

$491
(American Airlines)
From Hilton Head Island to Caribbean

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 March 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/31. 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 5/156:20 pmHHH - PUJ
1 stop16h 15mAmerican Airlines
Thu 5/222:12 pmPUJ - HHH
1 stop24h 31mAmerican Airlines
Deal found 3/31$491
This American Airlines deal was found by Cheapflights users on 3/30. 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 7/92:45 pmHHH - SJU
1 stop9h 42mAmerican Airlines
Fri 7/187:00 pmSJU - HHH
2 stops16h 26mAmerican Airlines
Deal found 3/30$503
This Delta deal was found by Cheapflights users on 3/30. 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.
Wed 7/912:00 pmHHH - SJU
1 stop7h 44mDelta
Fri 7/186:15 amSJU - HHH
1 stop9h 07mDelta
Deal found 3/30$513
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/116:06 pmHHH - MBJ
2 stops16h 39mAmerican Airlines
Mon 4/144:00 pmMBJ - HHH
2 stops19h 17mAmerican Airlines
Deal found 3/30$574
This United Airlines deal was found by Cheapflights users on 3/30. 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 4/14:18 pmHHH - PUJ
2 stops20h 22mUnited Airlines
Sat 4/54:35 pmPUJ - HHH
2 stops23h 02mUnited Airlines
Deal found 3/30$970

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 March 31, 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 IslandPunta Cana

HHH - PUJ

HHHPUJ

Hilton Head Island

Thu 5/15

6:20 pm-10:35 am

1 stop16h 15m

Punta Cana

Thu 5/22

2:12 pm-2:43 pm

1 stop24h 31m

$491

Hilton Head IslandMontego Bay

HHH - MBJ

HHHMBJ

Hilton Head Island

Fri 4/11

6:06 pm-9:45 am

2 stops16h 39m

Montego Bay Sangster Intl

Mon 4/14

4:00 pm-12:17 pm

2 stops19h 17m

$574

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Fri 4/25

12:47 pm-8:28 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Mon 4/28

7:15 am-5:36 pm

1 stop10h 21m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 March 31, 2025.

Food

6.5

Boarding

7.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Comfort

7.2

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation

Food

6.5

Boarding

7.5

Crew

8.0

Entertainment

6.9

Overall

7.2

Comfort

7.2

Reviews

1 / 20
6.0
Good

sheila,Mar 2025

DFW - MSP

We were delayed for 3 hours with no real reason or offer for compensation

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?

  • 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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