PWM - HHH

$336 Find Cheap Flights from Portland to Hilton Head Island

This is the cheapest round-trip 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 4/22. 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, 0 bags

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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$336
American Airlines
Wed 4/22Tue 4/28
PWM - HHH • 1 stop
Cheapest one-way
Multiple Airlines
Fri 11/28
PWM - HHH • multi-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
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

Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
5:46 am - 11:04 amPWM-HHH
5h 18m1 stop
American Airlines Logo
4:05 pm - 10:25 pmHHH-PWM
6h 20m1 stop
$336American Airlines
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Sat, Jan 17 - Wed, Jan 21
American Airlines Logo
7:00 am - 2:59 pmPWM-HHH
7h 59m1 stop
American Airlines Logo
3:29 pm - 10:07 pmHHH-PWM
6h 38m1 stop
$353American Airlines
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Sat, Jan 17 - Wed, Jan 21
American Airlines Logo
5:30 am - 12:20 pmPWM-HHH
6h 50m2 stops
American Airlines Logo
3:29 pm - 10:07 pmHHH-PWM
6h 38m1 stop
$358American Airlines
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Sat, Jan 17 - Wed, Jan 21
American Airlines Logo
6:00 am - 2:59 pmPWM-HHH
8h 59m2 stops
American Airlines Logo
12:51 pm - 11:43 pmHHH-PWM
10h 52m2 stops
$363American Airlines
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Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
7:06 am - 2:20 pmPWM-HHH
7h 14m2 stops
American Airlines Logo
4:05 pm - 10:25 pmHHH-PWM
6h 20m1 stop
$394American Airlines
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Sat, May 2 - Sat, May 9
American Airlines Logo
5:46 am - 11:04 amPWM-HHH
5h 18m1 stop
American Airlines Logo
11:32 am - 11:39 pmHHH-PWM
12h 07m1 stop
$497American Airlines
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Sat, May 2 - Sat, May 9
American Airlines Logo
5:46 am - 11:04 amPWM-HHH
5h 18m1 stop
American Airlines Logo
4:05 pm - 10:27 pmHHH-PWM
6h 22m2 stops
$515American Airlines
Find Deal
Wed, Apr 22 - Tue, Apr 28
American Airlines Logo
7:06 am - 2:20 pmPWM-HHH
7h 14m2 stops
American Airlines Logo
4:05 pm - 11:39 pmHHH-PWM
7h 34m2 stops
$520American Airlines
Find Deal
Sat, May 2 - Sat, May 9
American Airlines Logo
6:01 am - 5:36 pmPWM-HHH
11h 35m2 stops
American Airlines Logo
4:05 pm - 10:27 pmHHH-PWM
6h 22m2 stops
$553American Airlines
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Mon, Mar 23 - Fri, Mar 27
American Airlines Logo
10:53 am - 3:41 pmPWM-HHH
4h 48m1 stop
American Airlines Logo
6:20 pm - 10:50 pmHHH-PWM
4h 30m1 stop
$849American Airlines
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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.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$336
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly with an average 17% 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 $336 for a round-trip ticket.

  • 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 11042 reviews
6.9Entertainment
7.5Boarding
7.2Comfort
8.0Crew
6.4Food
Airline reviews

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

8.0 ExcellentWayne, Nov 2025MIA - BWI
Read more American Airlines reviews

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

I had a positive experience on American. I'm blind and traveling with a guide dog and the flight attendants were so kind, friendly, and helpful towards us. They checked in on us during the flight and they made us feel comfortable and welcomed. There was an hour delay before depature, but overall the flight was a smooth ride. I appreciate that there were no issues on this long flight back home.

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

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

Information on your arrival and departure airports

Portland (PWM)
Hilton Head Island (HHH)