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$430+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap 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 December 4, 2025.

This American Airlines deal was found by Cheapflights users on 12/2. 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 12/306:13 pmHHH - SJU
2 stops25h 58mAmerican Airlines
Sun 1/48:35 pmSJU - HHH
2 stops15h 09mAmerican Airlines
Deal found 12/2$1,243
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/306:13 pmHHH - SJU
2 stops25h 58mAmerican Airlines
Sat 1/310:03 pmSJU - HHH
2 stops17h 13mAmerican Airlines
Deal found 12/2$1,267
This American Airlines deal was found by Cheapflights users on 12/3. 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 12/296:13 pmHHH - SJU
2 stops22h 54mAmerican Airlines
Sat 1/36:00 amSJU - HHH
2 stops12h 43mAmerican Airlines
Deal found 12/3$1,315
This American Airlines deal was found by Cheapflights users on 12/3. 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 12/296:13 pmHHH - SJU
2 stops22h 54mAmerican Airlines
Sun 1/45:24 amSJU - HHH
2 stops9h 52mAmerican Airlines
Deal found 12/3$1,345

Find 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 December 4, 2025.

Round-trip from

$430
(American Airlines)
From Hilton Head Island to Puerto Rico
Search Deals

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 December 4, 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

Sat 1/10

12:54 pm-12:30 pm

2 stops22h 36m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:20 am-2:59 pm

1 stop7h 39m

$430

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 4/28

4:00 pm-11:50 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Fri 5/1

7:00 am-3:12 pm

2 stops32h 12m

$860

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Tue 12/30

6:13 pm-9:11 pm

2 stops25h 58m

San Juan Luis Munoz Marin Intl

Sat 1/3

10:03 pm-2:16 pm

2 stops17h 13m

$1,267

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 12/29

6:13 pm-6:07 pm

2 stops22h 54m

San Juan Luis Munoz Marin Intl

Sat 1/3

6:00 am-5:43 pm

2 stops12h 43m

$1,315

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 12/29

6:13 pm-6:07 pm

2 stops22h 54m

San Juan Luis Munoz Marin Intl

Sun 1/4

5:24 am-2:16 pm

2 stops9h 52m

$1,345

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

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, May is the cheapest month in which you can book a flight from Hilton Head Island to Puerto Rico (average of $155). Flying from Hilton Head Island to Puerto Rico in February is currently the most expensive (average of $293). 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 7h 50m. Fly via American Airlines or United Airlines to get the fastest option. Airlines will cover a distance of 1319 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, May is the cheapest month in which you can book a flight from Hilton Head Island to Puerto Rico (average of $155). Flying from Hilton Head Island to Puerto Rico in February is currently the most expensive (average of $293). 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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