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Hilton Head Island

$437+ Cheap flights from Pensacola to Hilton Head Island (PNS - HHH)

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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — HHH
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheap flight deals from Pensacola to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$437
(American Airlines)
Provider with most accurate pricing for Pensacola-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Hilton Head Island flights.
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From Pensacola to Hilton Head Island
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Find flight deals from Pensacola to Hilton Head Island

Cheapest flights from Pensacola to Hilton Head Island
Explore the most affordable flight options available from Pensacola to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 11/105:24 amPNS - HHH
1 stop6h 05mAmerican Airlines
Fri 11/141:02 pmHHH - PNS
1 stop4h 23mAmerican Airlines
Deal found 10/26$519
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/31:52 pmPNS - HHH
1 stop3h 45mAmerican Airlines
Wed 11/53:27 pmHHH - PNS
1 stop4h 06mAmerican Airlines
Deal found 10/26$647
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/56:00 amPNS - HHH
2 stops11h 37mAmerican Airlines
Fri 11/73:27 pmHHH - PNS
1 stop4h 06mAmerican Airlines
Deal found 10/27$652

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola to Hilton Head Island 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 October 28, 2025.
Use the filters below to find and compare flights from Pensacola to Hilton Head Island that are best for you.

Fly from

Pensacola

Fly to

Hilton Head Island

Route

Depart

Return

Price

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Tue 3/31

5:34 am-10:24 am

1 stop3h 50m

Hilton Head Island

Wed 4/1

4:10 pm-7:00 pm

1 stop3h 50m

$437

PensacolaHilton Head Island

PNS - HHH

PNSHHH

Pensacola

Mon 11/10

5:24 am-12:29 pm

1 stop6h 05m

Hilton Head Island

Fri 11/14

1:02 pm-4:25 pm

1 stop4h 23m

$519

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Compare providers for flights from Pensacola to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pensacola to Hilton Head Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Pensacola-Hilton Head Island flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pensacola-Hilton Head Island flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Pensacola-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-Hilton Head Island flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Pensacola-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pensacola to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Pensacola 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 Pensacola to Hilton Head Island

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

Currently, October is the cheapest month in which you can book a flight from Pensacola to Hilton Head Island (average of $96). Flying from Pensacola to Hilton Head Island in January is currently the most expensive (average of $280). 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 Pensacola to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Airlines like American Airlines fly from Pensacola to Hilton Head Island in about 3h 50m. The time it takes to get you to your destination can typically vary by up to . There are 401 mi between Pensacola and Hilton Head Island.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pensacola to Hilton Head Island.

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

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

    Currently, October is the cheapest month in which you can book a flight from Pensacola to Hilton Head Island (average of $96). Flying from Pensacola to Hilton Head Island in January is currently the most expensive (average of $280). 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

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton

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