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$385+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — SJU
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$385
(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 July 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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.
Mon 9/153:26 pmHHH - SJU
2 stops8h 11mAmerican Airlines
Mon 9/297:05 pmSJU - HHH
2 stops21h 42mAmerican Airlines
Deal found 7/30$385
This Delta deal was found by Cheapflights users on 7/29. 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.
Mon 9/1512:14 pmHHH - SJU
1 stop9h 46mDelta
Mon 9/297:30 amSJU - HHH
1 stop7h 55mDelta
Deal found 7/29$550
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Mon 9/1512:06 pmHHH - SJU
2 stops32h 32mUnited Airlines
Sun 9/281:05 amSJU - HHH
1 stop10h 11mUnited Airlines
Deal found 7/29$829
This United deal was found by Cheapflights users on 7/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/112:02 pmHHH - SJU
2 stops49h 27mMultiple Airlines
Sun 8/32:05 amSJU - HHH
2 stops33h 12mMultiple Airlines
Deal found 7/29$2,855

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 July 30, 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

Mon 9/15

3:26 pm-11:37 pm

2 stops8h 11m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:05 pm-4:47 pm

2 stops21h 42m

$385

Hilton Head IslandSan Juan

HHH - SJU

HHHSJU

Hilton Head Island

Mon 9/15

12:14 pm-10:00 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Mon 9/29

7:30 am-3:25 pm

1 stop7h 55m

$550

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-11:16 am

1 stop10h 11m

$829

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Hilton Head Island to Puerto Rico, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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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