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Cheap flights from Portland, Maine to Hilton Head Island from $443

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Hilton Head Island departing on 6/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Portland, Maine to Hilton Head Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:15 am - 2:13 pm
PWM
-
HHH
6h 58m
1 stop
American Airlines Logo
5:21 pm - 10:46 pm
HHH
-
PWM
5h 25m
1 stop
$443American Airlines
Mon, Jun 1 - Sun, Jun 7
American Airlines Logo
8:04 am - 4:32 pm
PWM
-
HHH
8h 28m
2 stops
American Airlines Logo
5:21 pm - 10:46 pm
HHH
-
PWM
5h 25m
1 stop
$512American Airlines
Mon, Jun 1 - Sun, Jun 7
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:59 pm
HHH
-
PWM
10h 14m
2 stops
$524United Airlines
Tue, Sep 1 - Wed, Sep 2
Delta Logo
6:00 am - 11:23 am
PWM
-
HHH
5h 23m
1 stop
Delta Logo
4:00 pm - 11:11 pm
HHH
-
PWM
7h 11m
1 stop
$553Delta
Sun, Sep 13 - Fri, Sep 18
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:59 pm
HHH
-
PWM
10h 14m
2 stops
$566United Airlines
Tue, Sep 1 - Wed, Sep 2
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:31 pm
HHH
-
PWM
9h 46m
1 stop
$582United Airlines
Tue, Sep 1 - Wed, Sep 2
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:31 pm
HHH
-
PWM
9h 46m
1 stop
$610United Airlines
Tue, Sep 1 - Wed, Sep 2
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:31 pm
HHH
-
PWM
9h 46m
1 stop
$640United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:31 pm
HHH
-
PWM
9h 46m
1 stop
$645United Airlines
Tue, Aug 25 - Wed, Aug 26
United Airlines Logo
6:00 am - 12:52 pm
PWM
-
HHH
6h 52m
1 stop
United Airlines Logo
1:45 pm - 11:59 pm
HHH
-
PWM
10h 14m
2 stops
$648United Airlines
Tue, Aug 25 - Wed, Aug 26

American Airlines flights from Portland, Maine to Hilton Head Island

Our best American Airlines deals on Portland, Maine to Hilton Head Island flight tickets
American Airlines
Jun 1
PWM7:15 amPortland
6h 58m
1 stop
HHH2:13 pmHilton Head Island
Jun 7
HHH5:21 pmHilton Head Island
5h 25m
1 stop
PWM10:46 pmPortland
$443
American Airlines
May 14
PWM6:00 amPortland
10h 34m
2 stops
HHH4:34 pmHilton Head Island
May 28
HHH5:21 pmHilton Head Island
5h 26m
1 stop
PWM10:47 pmPortland
$448
American Airlines
Jun 1
PWM8:04 amPortland
8h 28m
2 stops
HHH4:32 pmHilton Head Island
Jun 7
HHH5:21 pmHilton Head Island
5h 25m
1 stop
PWM10:46 pmPortland
$512

Delta flights from Portland, Maine to Hilton Head Island

Our best Delta deals on Portland, Maine to Hilton Head Island flight tickets
Delta
Sep 13
PWM6:00 amPortland
5h 23m
1 stop
HHH11:23 amHilton Head Island
Sep 18
HHH4:00 pmHilton Head Island
7h 11m
1 stop
PWM11:11 pmPortland
$553
Delta
Jun 7
PWM6:00 amPortland
5h 31m
1 stop
HHH11:31 amHilton Head Island
Jun 13
HHH4:20 pmHilton Head Island
5h 15m
1 stop
PWM9:35 pmPortland
$686
Delta
Sep 13
PWM6:00 amPortland
9h 20m
2 stops
HHH3:20 pmHilton Head Island
Sep 18
HHH4:00 pmHilton Head Island
7h 11m
1 stop
PWM11:11 pmPortland
$801

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine to Hilton Head Island that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 8, 2026.
Use the filters below to find and compare flights from Portland, Maine to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 6/1

7:15 am-2:13 pm

1 stop6h 58m

Hilton Head Island

Sun 6/7

5:21 pm-10:46 pm

1 stop5h 25m

$443

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 6/1

8:04 am-4:32 pm

2 stops8h 28m

Hilton Head Island

Sun 6/7

5:21 pm-10:46 pm

1 stop5h 25m

$512

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 9/1

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 9/2

1:45 pm-11:59 pm

2 stops10h 14m

$524

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sun 9/13

6:00 am-11:23 am

1 stop5h 23m

Hilton Head Island

Fri 9/18

4:00 pm-11:11 pm

1 stop7h 11m

$553

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 9/1

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 9/2

1:45 pm-11:59 pm

2 stops10h 14m

$566

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 9/1

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 9/2

1:45 pm-11:31 pm

1 stop9h 46m

$582

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 9/1

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 9/2

1:45 pm-11:31 pm

1 stop9h 46m

$610

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 8/25

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 8/26

1:45 pm-11:31 pm

1 stop9h 46m

$640

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 8/25

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 8/26

1:45 pm-11:31 pm

1 stop9h 46m

$645

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 8/25

6:00 am-12:52 pm

1 stop6h 52m

Hilton Head Island

Wed 8/26

1:45 pm-11:59 pm

2 stops10h 14m

$648

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Hilton Head Island from

How to get the cheapest flight ticket from Portland, Maine to Hilton Head Island

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Portland, Maine and Hilton Head Island?

What is the cheapest month to fly to Hilton Head Island?

If you don’t want to visit Hilton Head Island in August, then you should wait until January to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $0.

When to book flights from Portland, Maine to Hilton Head Island

Are you open to changing your travel dates? Check out the ideal times to fly from Portland, Maine to Hilton Head Island according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Portland, Maine to Hilton Head Island (PWM to HHH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Portland, Maine to Hilton Head Island

Fastest flight time

5h 23m

Direct flights

None
The fastest flight from Portland, Maine to Hilton Head Island takes 5h 23m
There are no direct flights from Portland, Maine to Hilton Head Island. There are no popular flight routes from Portland, Maine to Hilton Head Island.
Search flight deals

Frequently asked questions about flying from Portland, Maine to Hilton Head Island

  • How far is Portland to Hilton Head Island by plane?

    The straight-line distance from Portland to Hilton Head Island is 973.5 mi. In terms of flight time, this usually takes a little over 5h 23m.

  • When did momondo last update prices for flights from Portland Airport to Hilton Head Island Airport?

    Prices for flights from Portland Airport to Hilton Head Island Airport refresh daily.

  • How many operators does momondo search for flights from Portland Airport to Hilton Head Island Airport?

  • How old do you have to be to fly from Portland Airport to Hilton Head Island Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Portland Airport to Hilton Head Island Airport.

  • What documentation or ID do you need to fly to Hilton Head Island Airport?

    The travel and health documents required for your trip to Hilton Head Island Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Hilton Head Island Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Portland, Maine to Hilton Head Island?

Best airlines flying from Portland, Maine to Hilton Head Island

Compare and see reviews for airlines that fly from Portland, Maine to Hilton Head Island with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $279Free CancellationRating
7.1
11,667 reviews
Search American Airlines flights

Traveling to a place near Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort
Bluffton
Daufuskie Island

Why use momondo?

Why should I use momondo to find a flight deal from Portland to Hilton Head Island?

Finding the right flight to Hilton Head Island from Portland is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Hilton Head Island quick and easy, saving you time and money.

Can I find flights from Portland to Hilton Head Island with flexible booking policies on momondo?

Yes. All flights to Hilton Head Island from Portland on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Portland to Hilton Head Island?

Once all potential Portland to Hilton Head Island flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Portland to Hilton Head Island right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Hilton Head Island, momondo offers a useful price alert feature which will track prices for flights to Hilton Head Island from Portland and alert you when they change.

An easier way to manage your Hilton Head Island trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
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Sun 6/7
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