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Cheap flights from Portland, Maine to Hilton Head Island from $310

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 3/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
7:00 am - 11:53 am
PWM
-
HHH
4h 53m
1 stop
American Airlines Logo
6:15 pm - 10:50 pm
HHH
-
PWM
4h 35m
1 stop
$310American Airlines
Wed, Mar 4 - Mon, Mar 9
American Airlines Logo
6:00 am - 3:01 pm
PWM
-
HHH
9h 01m
2 stops
American Airlines Logo
6:15 pm - 10:50 pm
HHH
-
PWM
4h 35m
1 stop
$315American Airlines
Wed, Mar 4 - Mon, Mar 9
Delta Logo
6:00 am - 11:28 am
PWM
-
HHH
5h 28m
1 stop
Delta Logo
4:00 pm - 11:24 pm
HHH
-
PWM
7h 24m
1 stop
$325Delta
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
10:58 am - 3:41 pm
PWM
-
HHH
4h 43m
1 stop
American Airlines Logo
6:15 pm - 10:50 pm
HHH
-
PWM
4h 35m
1 stop
$336American Airlines
Wed, Mar 11 - Wed, Mar 18
American Airlines Logo
6:00 am - 10:30 am
PWM
-
HHH
4h 30m
1 stop
American Airlines Logo
5:54 pm - 10:40 pm
HHH
-
PWM
4h 46m
1 stop
$337American Airlines
Thu, May 28 - Mon, Jun 1
American Airlines Logo
6:00 am - 2:22 pm
PWM
-
HHH
8h 22m
2 stops
American Airlines Logo
6:15 pm - 10:50 pm
HHH
-
PWM
4h 35m
1 stop
$374American Airlines
Mon, Mar 9 - Wed, Mar 11
American Airlines Logo
6:00 am - 2:22 pm
PWM
-
HHH
8h 22m
2 stops
American Airlines Logo
2:58 pm - 11:55 pm
HHH
-
PWM
8h 57m
2 stops
$380American Airlines
Mon, Mar 9 - Wed, Mar 11
Delta Logo
6:00 am - 3:20 pm
PWM
-
HHH
9h 20m
2 stops
Delta Logo
4:00 pm - 11:24 pm
HHH
-
PWM
7h 24m
1 stop
$402Delta
Tue, Apr 14 - Tue, Apr 21
Delta Logo
6:30 am - 3:18 pm
PWM
-
HHH
8h 48m
2 stops
Delta Logo
4:00 pm - 11:11 pm
HHH
-
PWM
7h 11m
1 stop
$407Delta
Thu, May 28 - Mon, Jun 1
American Airlines Logo
6:00 am - 2:22 pm
PWM
-
HHH
8h 22m
2 stops
American Airlines Logo
2:54 pm - 10:13 pm
HHH
-
PWM
7h 19m
1 stop
$408American Airlines
Fri, Apr 3 - Tue, Apr 7

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
Mar 4
PWM7:00 amPortland
4h 53m
1 stop
HHH11:53 amHilton Head Island
Mar 9
HHH6:15 pmHilton Head Island
4h 35m
1 stop
PWM10:50 pmPortland
$310
American Airlines
Mar 4
PWM6:00 amPortland
9h 01m
2 stops
HHH3:01 pmHilton Head Island
Mar 9
HHH6:15 pmHilton Head Island
4h 35m
1 stop
PWM10:50 pmPortland
$315
American Airlines
Mar 11
PWM10:58 amPortland
4h 43m
1 stop
HHH3:41 pmHilton Head Island
Mar 18
HHH6:15 pmHilton Head Island
4h 35m
1 stop
PWM10:50 pmPortland
$336

Delta flights from Portland, Maine to Hilton Head Island

Our best Delta deals on Portland, Maine to Hilton Head Island flight tickets
Delta
Apr 14
PWM6:00 amPortland
5h 28m
1 stop
HHH11:28 amHilton Head Island
Apr 21
HHH4:00 pmHilton Head Island
7h 24m
1 stop
PWM11:24 pmPortland
$325
Delta
Apr 14
PWM6:00 amPortland
9h 20m
2 stops
HHH3:20 pmHilton Head Island
Apr 21
HHH4:00 pmHilton Head Island
7h 24m
1 stop
PWM11:24 pmPortland
$402
Delta
May 28
PWM6:30 amPortland
8h 48m
2 stops
HHH3:18 pmHilton Head Island
Jun 1
HHH4:00 pmHilton Head Island
7h 11m
1 stop
PWM11:11 pmPortland
$407

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 January 29, 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

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 3/4

7:00 am-11:53 am

1 stop4h 53m

Hilton Head Island

Mon 3/9

6:15 pm-10:50 pm

1 stop4h 35m

$310

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 3/4

6:00 am-3:01 pm

2 stops9h 01m

Hilton Head Island

Mon 3/9

6:15 pm-10:50 pm

1 stop4h 35m

$315

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 4/14

6:00 am-11:28 am

1 stop5h 28m

Hilton Head Island

Tue 4/21

4:00 pm-11:24 pm

1 stop7h 24m

$325

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 3/11

10:58 am-3:41 pm

1 stop4h 43m

Hilton Head Island

Wed 3/18

6:15 pm-10:50 pm

1 stop4h 35m

$336

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 5/28

6:00 am-10:30 am

1 stop4h 30m

Hilton Head Island

Mon 6/1

5:54 pm-10:40 pm

1 stop4h 46m

$337

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 3/9

6:00 am-2:22 pm

2 stops8h 22m

Hilton Head Island

Wed 3/11

6:15 pm-10:50 pm

1 stop4h 35m

$374

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 3/9

6:00 am-2:22 pm

2 stops8h 22m

Hilton Head Island

Wed 3/11

2:58 pm-11:55 pm

2 stops8h 57m

$380

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 4/14

6:00 am-3:20 pm

2 stops9h 20m

Hilton Head Island

Tue 4/21

4:00 pm-11:24 pm

1 stop7h 24m

$402

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 5/28

6:30 am-3:18 pm

2 stops8h 48m

Hilton Head Island

Mon 6/1

4:00 pm-11:11 pm

1 stop7h 11m

$407

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Fri 4/3

6:00 am-2:22 pm

2 stops8h 22m

Hilton Head Island

Tue 4/7

2:54 pm-10:13 pm

1 stop7h 19m

$408

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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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 cheapest airline that flies from Portland to Hilton Head Island?

American Airlines is the most popular carrier operating from Portland to Hilton Head Island

What airlines fly to Hilton Head Island?

JetBlue, Delta and Breeze Airways are the top three most popular airlines that fly to Hilton Head Island from Portland, Maine according to our data. JetBlue is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Hilton Head Island. Keep in mind that there are 8 different airlines that fly to Hilton Head Island on a routine basis, so you have a few additional options to choose from.

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

4h 46m

Direct flights

None
The fastest flight from Portland, Maine to Hilton Head Island takes 4h 46m
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

  • 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 4h 46m.

  • 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
7.2
11,205 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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