$365+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Hilton Head Island to Caribbean Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 June 12, 2025.
Round-trip from | $365 (American Airlines) |
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Find flight deals from Hilton Head Island to Caribbean Islands
Cheapest flights from Hilton Head Island to Caribbean IslandsExplore 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 June 12, 2025.
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 June 12, 2025.
This American Airlines deal was found by Cheapflights users on 6/11. 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.
This Delta deal was found by Cheapflights users on 6/10. 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.
This United Airlines deal was found by Cheapflights users on 6/11. 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.
This United Airlines deal was found by Cheapflights users on 6/10. 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.
This American Airlines deal was found by Cheapflights users on 6/12. 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.
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 June 12, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Hilton Head IslandSan Juan
HHH - SJU
HHHSJU
Hilton Head Island
Mon 9/15
3:26 pm-11:37 pm
2 stops8h 11m
San Juan Luis Munoz Marin Intl
Mon 9/29
1:36 pm-12:17 pm
2 stops22h 41m
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
Hilton Head IslandWillemstad
HHH - CUR
HHHCUR
Hilton Head Island
Wed 6/25
12:03 pm-12:17 pm
2 stops24h 14m
Willemstad Hato Int.
Thu 8/21
1:22 pm-11:21 am
3 stops21h 59m
Hilton Head IslandSan Juan
HHH - SJU
HHHSJU
Hilton Head Island
Mon 9/15
12:06 pm-8:38 pm
2 stops32h 32m
San Juan Luis Munoz Marin Intl
Sun 9/28
1:05 am-11:22 am
1 stop10h 17m
Hilton Head IslandMontego Bay
HHH - MBJ
HHHMBJ
Hilton Head Island
Sun 6/22
6:07 pm-12:10 pm
2 stops19h 03m
Montego Bay Sangster Intl
Sun 6/29
5:05 pm-12:27 pm
2 stops18h 22m
Hilton Head IslandMarsh Harbour
HHH - MHH
HHHMHH
Hilton Head Island
Sun 7/6
1:45 pm-12:00 pm
1 stop22h 15m
Hilton Head IslandSan Juan
HHH - SJU
HHHSJU
Hilton Head Island
Thu 8/21
12:11 pm-10:07 pm
1 stop9h 56m
Hilton Head IslandSan Juan
HHH - SJU
HHHSJU
Hilton Head Island
Thu 8/21
12:06 pm-12:34 pm
2 stops24h 28m
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.
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, 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 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.
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 June 12, 2025.
Get a feel of what it's like to fly with Delta, United Airlines and American Airlines from Hilton Head Island to Caribbean Islands by reading reviews from past customers. 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.
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC
Overall
Food
Boarding
Comfort
Entertainment
Crew
Reviews
Kim,May 2025
PIH - SLC