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$365+ Cheap flights from Hilton Head Island (HHH) to Puerto Rico

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Puerto Rico

Keep the following information in mind while searching for Hilton Head Island to Puerto Rico flight deals. Data was last updated September 16, 2025.

Round-trip from

$365
(American Airlines)
From Hilton Head Island to Puerto Rico
Search Deals

Find flight deals from Hilton Head Island to Puerto Rico

Cheapest flights from Hilton Head Island to Puerto Rico
Explore the most affordable flight options available from Hilton Head Island to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 12/46:52 pmHHH - SJU
2 stops16h 07mAmerican Airlines
Mon 12/86:42 pmSJU - HHH
2 stops21h 15mAmerican Airlines
Deal found 9/15$365
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/143:32 pmHHH - SJU
1 stop6h 38mAmerican Airlines
Wed 10/227:45 amSJU - HHH
1 stop9h 06mAmerican Airlines
Deal found 9/14$515
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/143:32 pmHHH - SJU
1 stop6h 38mAmerican Airlines
Tue 10/217:45 amSJU - HHH
1 stop9h 06mAmerican Airlines
Deal found 9/14$535
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/143:32 pmHHH - SJU
1 stop6h 38mAmerican Airlines
Mon 10/207:10 amSJU - HHH
1 stop7h 22mAmerican Airlines
Deal found 9/14$575
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/153:26 pmHHH - SJU
2 stops8h 11mAmerican Airlines
Mon 9/291:37 pmSJU - HHH
2 stops22h 40mAmerican Airlines
Deal found 9/14$605
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 9/1912:06 pmHHH - SJU
2 stops27h 36mUnited Airlines
Sun 9/211:05 amSJU - HHH
1 stop10h 20mUnited Airlines
Deal found 9/15$1,029

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Puerto Rico 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 September 16, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Puerto Rico that are best for you.

Fly from

Hilton Head Island

Fly to

Puerto Rico

Route

Depart

Return

Price

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Thu 12/4

6:52 pm-11:59 am

2 stops16h 07m

San Juan Luis Munoz Marin Intl

Mon 12/8

6:42 pm-2:57 pm

2 stops21h 15m

$365

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 10/14

3:32 pm-10:10 pm

1 stop6h 38m

San Juan Luis Munoz Marin Intl

Wed 10/22

7:00 am-4:51 pm

2 stops9h 51m

$515

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 10/14

3:32 pm-10:10 pm

1 stop6h 38m

San Juan Luis Munoz Marin Intl

Tue 10/21

7:00 am-4:51 pm

2 stops9h 51m

$515

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Best time to book a flight from Hilton Head Island to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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 Puerto Rico

What is the cheapest month to book a flight from Hilton Head Island to Puerto Rico?

Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Puerto Rico (average of $254). Flying from Hilton Head Island to Puerto Rico 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Puerto Rico. 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 Puerto Rico?

    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 Puerto Rico.

  • How long is the flight from Hilton Head Island to Puerto Rico?

    There are many flights that can get you from Hilton Head Island to Puerto Rico in 16h 07m. Fly via American Airlines to get the fastest option. Airlines will cover a distance of 1319 mi.

  • Can I find deals for flights from Hilton Head Island to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Puerto Rico?

    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 Puerto Rico.

  • Can I find deals for business class flights from Hilton Head Island to Puerto Rico?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Puerto Rico 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 Puerto Rico?

    Currently, September is the cheapest month in which you can book a flight from Hilton Head Island to Puerto Rico (average of $254). Flying from Hilton Head Island to Puerto Rico 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.

See more FAQs

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Alternative routes for Hilton Head Island to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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