PWM - HHH

$303 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 3/4. 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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Everything you should know

Cheapest round-trip
$303
American Airlines
Wed 3/4Wed 3/11
PWM - HHH • 1 stop
Cheapest one-way
$425
American Airlines
Fri 2/20
PWM - HHH • 1 stop
Top airlines
Delta
Cheapest • from $303 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Mar 4 - Wed, Mar 11
American Airlines Logo
10:55 am - 3:41 pm
PWM
-
HHH
4h 46m
1 stop
American Airlines Logo
6:15 pm - 10:50 pm
HHH
-
PWM
4h 35m
1 stop
$303American Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
10:55 am - 3:41 pm
PWM
-
HHH
4h 46m
1 stop
American Airlines Logo
2:58 pm - 11:55 pm
HHH
-
PWM
8h 57m
2 stops
$308American Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
6:00 am - 3:01 pm
PWM
-
HHH
9h 01m
2 stops
American Airlines Logo
2:58 pm - 11:55 pm
HHH
-
PWM
8h 57m
2 stops
$314American Airlines
Tue, Apr 14 - Tue, Apr 21
Delta Logo
6:00 am - 11:18 am
PWM
-
HHH
5h 18m
1 stop
Delta Logo
11:58 am - 11:24 pm
HHH
-
PWM
11h 26m
2 stops
$336Delta
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
7:00 am - 2:59 pm
PWM
-
HHH
7h 59m
1 stop
American Airlines Logo
3:29 pm - 10:07 pm
HHH
-
PWM
6h 38m
1 stop
$347American Airlines
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
7:00 am - 12:20 pm
PWM
-
HHH
5h 20m
1 stop
American Airlines Logo
12:51 pm - 10:54 pm
HHH
-
PWM
10h 03m
2 stops
$352American Airlines
Thu, Jan 29 - Mon, Feb 2
American Airlines Logo
6:00 am - 2:59 pm
PWM
-
HHH
8h 59m
2 stops
American Airlines Logo
3:29 pm - 10:54 pm
HHH
-
PWM
7h 25m
2 stops
$358American Airlines
Wed, Feb 25 - Sat, Feb 28
American Airlines Logo
6:00 am - 3:01 pm
PWM
-
HHH
9h 01m
2 stops
American Airlines Logo
6:20 pm - 10:50 pm
HHH
-
PWM
4h 30m
1 stop
$374American Airlines
Wed, Feb 25 - Fri, Mar 6
American Airlines Logo
6:00 am - 3:01 pm
PWM
-
HHH
9h 01m
2 stops
American Airlines Logo
6:20 pm - 10:50 pm
HHH
-
PWM
4h 30m
1 stop
$385American Airlines
Tue, Apr 14 - Tue, Apr 21
Delta Logo
6:00 am - 3:10 pm
PWM
-
HHH
9h 10m
2 stops
Delta Logo
11:58 am - 11:24 pm
HHH
-
PWM
11h 26m
2 stops
$404Delta
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.

Which airlines provide the cheapest flights from Portland to Hilton Head Island?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Hilton Head Island were found on Delta ($303) and American Airlines ($303).

Which airlines fly non-stop between Portland and Hilton Head Island?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Portland to Hilton Head Island.

There is just one airline that flies from Portland to Hilton Head Island direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is $258.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$303
Best time to beat the crowds with an average 46% drop in price.
Most popular time to fly and prices are also 23% lower on average.
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 $425 for a one-way ticket and $303 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 11129 reviews
6.4Food
8.0Crew
7.2Comfort
6.9Entertainment
7.5Boarding
Airline reviews

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

6.0 GoodKathleen, Jan 2026
LGA - MCO
Read more American Airlines reviews

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

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)