$149 Cheap Flights from Portland (PWM) to Hilton Head Island (HHH)

View $149 flight on Sat, Oct 25, 2025Opens in a new window

Popular airlines from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH)

Cheap Flights from Portland to Hilton Head Island (PWM-HHH)

Prices were available within the past 7 days and start at $149 for one-way flights and $259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Nov 12 - Sat, Nov 15
PWM
Portland
HHH
Hilton Head Island
$259 Roundtrip, found 2 hours ago
$259
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Nov 12 from Portland to Hilton Head Island, returning Sat, Nov 15, priced at $259 found 2 hours ago
American Airlines
Thu, Oct 30 - Mon, Nov 3
PWM
Portland
HHH
Hilton Head Island
$268 Roundtrip, found 2 days ago
$268
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 30 from Portland to Hilton Head Island, returning Mon, Nov 3, priced at $268 found 2 days ago
American Airlines
Thu, Oct 30 - Mon, Nov 3
PWM
Portland
HHH
Hilton Head Island
$274 Roundtrip, found 4 days ago
$274
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Oct 30 from Portland to Hilton Head Island, returning Mon, Nov 3, priced at $274 found 4 days ago
American Airlines
Fri, Oct 24 - Tue, Oct 28
PWM
Portland
HHH
Hilton Head Island
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Oct 24 from Portland to Hilton Head Island, returning Tue, Oct 28, priced at $277 found 4 days ago
American Airlines
Thu, Oct 30 - Mon, Nov 3
PWM
Portland
HHH
Hilton Head Island
$283 Roundtrip, found 19 hours ago
$283
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Thu, Oct 30 from Portland to Hilton Head Island, returning Mon, Nov 3, priced at $283 found 19 hours ago
American Airlines
Thu, Oct 30 - Mon, Nov 3
PWM
Portland
HHH
Hilton Head Island
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Oct 30 from Portland to Hilton Head Island, returning Mon, Nov 3, priced at $289 found 6 days ago
Delta
Sat, Oct 25 - Sat, Nov 1
PWM
Portland
HHH
Hilton Head Island
$301 Roundtrip, found 4 days ago
$301
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 25 from Portland to Hilton Head Island, returning Sat, Nov 1, priced at $301 found 4 days ago
American Airlines
Wed, Nov 19 - Tue, Dec 9
PWM
Portland
HHH
Hilton Head Island
$329 Roundtrip, just found
$329
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov 19 from Portland to Hilton Head Island, returning Tue, Dec 9, priced at $329 just found
American Airlines
Wed, Nov 19 - Sat, Dec 6
PWM
Portland
HHH
Hilton Head Island
$334 Roundtrip, just found
$334
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov 19 from Portland to Hilton Head Island, returning Sat, Dec 6, priced at $334 just found
United
Mon, Apr 6 - Tue, Apr 14
PWM
Portland
HHH
Hilton Head Island
$541 Roundtrip, found 6 days ago
$541
Roundtrip
found 6 days ago
Select United flight, departing Mon, Apr 6 from Portland to Hilton Head Island, returning Tue, Apr 14, priced at $541 found 6 days ago

Alternative airports near Hilton Head Island

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Savannah - Hilton Head Intl. SAV. Cheapest option available. Average driving time to city center is 59 minutes. Flights from $278
SAV
Savannah - Hilton Head Intl.
Cheapest
Average driving time to city center59 min
Flights from $278

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH) cost?
Get a cheap one-way flight from $149 or cheap return flight from $259 from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH)?
Planning your trip for November is a great way to save, as it's the cheapest month for flights between PWM and HHH. You'll often find the lowest prices during the off-season.
What is the cheapest airline that flies from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH)?
To find the cheapest airline flying from PWM to HHH, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH)?
Direct flights from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel details and click on either "1 Stop" or "2+ Stops."
What day of the week has the most flights from PWM to HHH?
Generally you'll have the most choice when it comes to flights on a Friday. Tuesdays are often the quietest.* But this can vary based on the airline, season and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH)?
To touch down at Hilton Head Island Airport (HHH) without delays, pick a flight that leaves Portland Intl. Jetport Airport (PWM) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH) last-minute?
Last-minute fares from PWM to HHH are usually more expensive. To lock in the cheapest rates, start searching for flights as soon as possible. That said, if you're flexible with your travel dates, you may score a cheap ticket right before you leave.
Is it cheaper to book a PWM to HHH flight and hotel package?
Securing a PWM to HHH flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our impressive range of hotels and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to Hilton Head Island Airport (HHH)?
It's usually possible to reschedule or cancel your PWM to HHH flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Check your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

Travel information

Origin airport
Portland Intl. Jetport
Destination airport
Hilton Head Island
Airlines serving
American Airlines, Delta, United
Roundtrip price
$258
Distance
969 mi

Book with confidence

Portland to Hilton Head Island Flights

The cheapest times to fly from Portland to Hilton Head Island

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Hilton Head Island are during the month of November. You can find some of the cheapest flights from Portland to Hilton Head Island with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Hilton Head Island

Sunday is one of the best days to book for cheap flights from Portland to Hilton Head Island: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Hilton Head Island

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Hilton Head Island in 2025. You can also book with separate airlines for your outbound and return journeys, from $149 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Hilton Head Island flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Hilton Head Island airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Portland to Hilton Head Island Flights

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*Available to One Key members.