$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
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Hilton Head Island to Caribbean 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
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) |
|---|
Find flight deals from Hilton Head Island to Caribbean
Cheapest flights from Hilton Head Island to CaribbeanExplore 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.
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![American Airlines logo]()
$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![American Airlines logo]()
$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![Delta logo]()
$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![American Airlines logo]()
$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![United Airlines logo]()
$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
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
Goodsheila,Mar 2025
DFW - MSP
Food
6.5
Boarding
7.5
Crew
8.0
Entertainment
6.9
Overall
7.2
Comfort
7.2
Reviews
1 / 20
6.0
Goodsheila,Mar 2025
DFW - MSP