PDX - HHH

$232 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 4/29. 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
$389
American Airlines
Tue 4/14Tue 4/21
PDX - HHH • 1 stop
Cheapest one-way
$232
American Airlines
Wed 4/29
PDX - HHH • 2 stops
Top airlines
American Airlines
Cheapest • from $389 (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 (PDX-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, Apr 14 - Tue, Apr 21
American Airlines Logo
11:23 pm - 12:37 pm
PDX
-
HHH
10h 14m
1 stop
American Airlines Logo
2:54 pm - 8:19 pm
HHH
-
PDX
8h 25m
1 stop
$389American Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
11:23 pm - 10:32 am
PDX
-
HHH
8h 09m
1 stop
American Airlines Logo
2:54 pm - 11:53 pm
HHH
-
PDX
11h 59m
2 stops
$394American Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
11:47 pm - 2:26 pm
PDX
-
HHH
11h 39m
2 stops
American Airlines Logo
11:17 am - 10:42 pm
HHH
-
PDX
14h 25m
2 stops
$399American Airlines
Fri, Mar 6 - Wed, Mar 11
American Airlines Logo
9:44 pm - 10:33 am
PDX
-
HHH
9h 49m
1 stop
American Airlines Logo
2:58 pm - 8:44 pm
HHH
-
PDX
8h 46m
1 stop
$414American Airlines
Fri, Mar 6 - Wed, Mar 11
American Airlines Logo
9:44 pm - 10:33 am
PDX
-
HHH
9h 49m
1 stop
American Airlines Logo
2:58 pm - 12:34 am
HHH
-
PDX
12h 36m
2 stops
$419American Airlines
Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
11:23 pm - 10:32 am
PDX
-
HHH
8h 09m
1 stop
American Airlines Logo
2:54 pm - 8:19 pm
HHH
-
PDX
8h 25m
1 stop
$447American Airlines
Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
11:47 pm - 2:26 pm
PDX
-
HHH
11h 39m
2 stops
American Airlines Logo
2:54 pm - 8:19 pm
HHH
-
PDX
8h 25m
1 stop
$452American Airlines
Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
11:47 pm - 2:26 pm
PDX
-
HHH
11h 39m
2 stops
American Airlines Logo
1:08 pm - 11:53 pm
HHH
-
PDX
13h 45m
2 stops
$458American Airlines
Thu, Apr 16 - Sat, Apr 18
American Airlines Logo
10:23 pm - 10:32 am
PDX
-
HHH
9h 09m
1 stop
American Airlines Logo
2:54 pm - 11:53 pm
HHH
-
PDX
11h 59m
2 stops
$511American Airlines
Fri, Mar 6 - Wed, Mar 11
American Airlines Logo
5:43 pm - 10:33 am
PDX
-
HHH
13h 50m
2 stops
American Airlines Logo
11:03 am - 9:52 pm
HHH
-
PDX
13h 49m
2 stops
$516American Airlines
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 American Airlines ($389) and United Airlines ($563).

Find deals

Good to know

Low seasonNovember
Cheapest flight$232
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly and prices are also 6% 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 $232 for a one-way ticket and $389 for a round-trip.

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

    A passport is not required to fly from Portland to Hilton Head Island.

  • 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 11212 reviews
7.2Comfort
6.9Entertainment
6.4Food
7.5Boarding
8.0Crew
Airline reviews

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

2.0 MediocreSteven, Feb 2026
DCA - PVD
Read more American Airlines reviews

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

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

Information on your arrival and departure airports

Portland (PDX)
Hilton Head Island (HHH)