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 11/9. 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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Flights 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

Tue, Sep 2 - Fri, Sep 5
United Airlines Logo
6:00 am - 11:25 amPWM-HHH
5h 25m1 stop
United Airlines Logo
12:06 pm - 6:26 pmHHH-PWM
6h 20m1 stop
$357United Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
American Airlines Logo
5:41 am - 10:58 amPWM-HHH
5h 17m1 stop
American Airlines Logo
11:29 am - 4:39 pmHHH-PWM
5h 10m1 stop
$369American Airlines
Find Deal
Tue, Sep 2 - Fri, Sep 5
Delta Logo
6:00 am - 11:31 amPWM-HHH
5h 31m1 stop
Delta Logo
12:11 pm - 12:48 amHHH-PWM
12h 37m2 stops
$405Delta
Find Deal
Thu, Nov 6 - Sun, Nov 9
American Airlines Logo
5:41 am - 10:58 amPWM-HHH
5h 17m1 stop
American Airlines Logo
6:40 pm - 11:49 amHHH-PWM
17h 09m2 stops
$417American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
6:00 am - 10:34 amPWM-HHH
4h 34m1 stop
American Airlines Logo
11:04 am - 11:45 pmHHH-PWM
12h 41m1 stop
$436American Airlines
Find Deal
Sun, Nov 16 - Sat, Nov 22
American Airlines Logo
5:41 am - 10:59 amPWM-HHH
5h 18m1 stop
American Airlines Logo
2:51 pm - 11:38 pmHHH-PWM
8h 47m2 stops
$468American Airlines
Find Deal
Tue, Sep 2 - Fri, Sep 5
American Airlines Logo
6:00 am - 3:05 pmPWM-HHH
9h 05m2 stops
American Airlines Logo
12:56 pm - 11:45 pmHHH-PWM
10h 49m2 stops
$488American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
6:00 am - 10:34 amPWM-HHH
4h 34m1 stop
American Airlines Logo
6:20 pm - 11:37 pmHHH-PWM
5h 17m1 stop
$498American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
6:00 am - 10:34 amPWM-HHH
4h 34m1 stop
American Airlines Logo
2:36 pm - 11:45 pmHHH-PWM
9h 09m2 stops
$532American Airlines
Find Deal
Sun, Nov 16 - Sat, Nov 22
American Airlines Logo
5:41 am - 6:09 pmPWM-HHH
12h 28m2 stops
American Airlines Logo
6:40 pm - 11:49 amHHH-PWM
17h 09m2 stops
$568American 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

Cheapest flight$149
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 $357 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, Star Alliance, and SkyTeam are the airline alliances operating flights between Portland and Hilton Head Island, with SkyTeam being the most commonly used for this route.

  • 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 10000 reviews
7.5Boarding
6.5Food
6.9Entertainment
8.0Crew
7.2Comfort
Airline reviews

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

6.0 Goodpaul, Aug 2025SEA - ORD
Read more American Airlines reviews

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

We had to turn around and head back to Manchester. Problem with a plane engine.

Flight was delayed. Staff at the gate effectively and proactively communicated about the delay.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

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

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