PWM - HHH

$149 Find Cheap Flights from Portland to Hilton Head Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Hilton Head Island departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Hilton Head Island

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Hilton Head Island, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Hilton Head Island, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$259
American Airlines
Fri 11/14Thu 11/20
PWM - HHH • 1 stop
Cheapest one-way
$149
American Airlines
Tue 11/11
PWM - HHH • 1 stop
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We hope you love your trip to Hilton Head Island!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Hilton Head Island that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Hilton Head Island

Fri, Nov 14 - Thu, Nov 20
American Airlines Logo
5:43 am - 10:58 amPWM-HHH
5h 15m1 stop
American Airlines Logo
11:32 am - 4:40 pmHHH-PWM
5h 08m1 stop
$259American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
6:00 am - 10:46 amPWM-HHH
4h 46m1 stop
American Airlines Logo
11:16 am - 4:44 pmHHH-PWM
5h 28m1 stop
$297American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
6:00 am - 10:46 amPWM-HHH
4h 46m1 stop
American Airlines Logo
3:32 pm - 12:08 pmHHH-PWM
20h 36m2 stops
$298American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
6:00 am - 2:32 pmPWM-HHH
8h 32m2 stops
American Airlines Logo
3:32 pm - 12:08 pmHHH-PWM
20h 36m2 stops
$303American Airlines
Find Deal
Fri, Nov 14 - Thu, Nov 20
American Airlines Logo
5:43 am - 10:58 amPWM-HHH
5h 15m1 stop
American Airlines Logo
2:51 pm - 11:41 pmHHH-PWM
8h 50m2 stops
$373American Airlines
Find Deal
Thu, Apr 2 - Wed, Apr 22
American Airlines Logo
7:50 am - 2:19 pmPWM-HHH
6h 29m1 stop
American Airlines Logo
6:07 pm - 10:25 pmHHH-PWM
4h 18m1 stop
$413American Airlines
Find Deal
Tue, Mar 31 - Wed, Apr 1
American Airlines Logo
7:50 am - 2:19 pmPWM-HHH
6h 29m1 stop
American Airlines Logo
6:25 pm - 10:30 pmHHH-PWM
4h 05m1 stop
$512American Airlines
Find Deal
Tue, Mar 31 - Wed, Apr 1
American Airlines Logo
5:44 am - 2:19 pmPWM-HHH
8h 35m2 stops
American Airlines Logo
4:10 pm - 10:30 pmHHH-PWM
6h 20m1 stop
$517American Airlines
Find Deal
Thu, Nov 6 - Tue, Nov 11
American Airlines Logo
5:43 am - 10:58 amPWM-HHH
5h 15m1 stop
American Airlines Logo
3:27 pm - 11:59 pmHHH-PWM
8h 32m2 stops
$521American Airlines
Find Deal
Sat, Mar 14 - Sat, Mar 21
American Airlines Logo
5:44 am - 2:19 pmPWM-HHH
8h 35m2 stops
American Airlines Logo
6:25 pm - 10:30 pmHHH-PWM
4h 05m1 stop
$522American Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Portland to Hilton Head Island flights

Get data-powered insights and trends into flights from Portland to Hilton Head Island to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Portland to Hilton Head Island?

The average price of all round-trip flights from Portland to Hilton Head Island clicked on KAYAK for each day over the last 12 months.

When flying from Portland to Hilton Head Island, you should consider leaving on a Wednesday and avoid Fridays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Tuesdays and the most expensive ones on Thursdays.

Good to know

Low seasonSeptember
Cheapest flight$149
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Portland to Hilton Head Island

When to book flights from Portland to Hilton Head Island

Are your dates flexible? Find out the best times to travel from Portland to Hilton Head Island based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Portland to Hilton Head Island

  • What is the cheapest flight from Portland to Hilton Head Island?

    In the last 3 days, the lowest price for a flight from Portland to Hilton Head Island was $149 for a one-way ticket and $259 for a round-trip.

  • Do I need a passport to fly between Portland and Hilton Head Island?

    No

  • Which aircraft models fly most regularly from Portland to Hilton Head Island?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to Hilton Head Island?

    oneworld is the only airline alliance operating flights between Portland and Hilton Head Island.

  • How does KAYAK find such low prices on flights from Portland to Hilton Head Island?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to Hilton Head Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Hilton Head Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Hilton Head Island from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to Hilton Head Island?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Hilton Head Island with an airline and back to Portland with another airline. Booking your flights between Portland and HHH can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to Hilton Head Island?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Hilton Head Island from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Portland to Hilton Head Island

 
See real verified KAYAK customer reviews for airlines flying from Portland to Hilton Head Island. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Hilton Head Island? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11046 reviews
6.9Entertainment
7.5Boarding
8.0Crew
7.2Comfort
6.4Food
Airline reviews

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

8.0 ExcellentRachel, Oct 2025CLE - ORD
Read more American Airlines reviews

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

You can plug your phone in & use their wifi to watch movies, etc, but the plane’s wifi was disconnected for most of the flight.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Everything you need to know for your flight from Portland to Hilton Head Island

Information on your arrival and departure airports

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