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Cheap flights from Portland, Maine to Hilton Head Island from $149

This is the cheapest one-way 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 11/9. 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 (PWM-HHH)

Cheap round-trip flights

Delta Logo
6:01 am - 3:30 pmPWM-HHH
9h 29m2 stops
Delta Logo
12:17 pm - 12:05 amHHH-PWM
11h 48m2 stops
$369Delta
Find Deal
Thu, Oct 9 - Tue, Oct 14
American Airlines Logo
7:05 am - 5:50 pmPWM-HHH
10h 45m2 stops
American Airlines Logo
6:20 pm - 11:37 pmHHH-PWM
5h 17m1 stop
$374American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
5:41 am - 10:59 amPWM-HHH
5h 18m1 stop
American Airlines Logo
11:29 am - 4:39 pmHHH-PWM
5h 10m1 stop
$377American Airlines
Find Deal
Mon, Nov 17 - Thu, Nov 20
American Airlines Logo
6:00 am - 10:46 amPWM-HHH
4h 46m1 stop
American Airlines Logo
11:16 am - 4:41 pmHHH-PWM
5h 25m1 stop
$381American Airlines
Find Deal
Thu, Oct 9 - Tue, Oct 14
American Airlines Logo
6:00 am - 10:34 amPWM-HHH
4h 34m1 stop
American Airlines Logo
6:20 pm - 11:37 pmHHH-PWM
5h 17m1 stop
$384American Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
American Airlines Logo
5:41 am - 2:57 pmPWM-HHH
9h 16m2 stops
American Airlines Logo
11:29 am - 4:39 pmHHH-PWM
5h 10m1 stop
$392American Airlines
Find Deal
Mon, Nov 17 - Thu, Nov 20
American Airlines Logo
6:00 am - 10:46 amPWM-HHH
4h 46m1 stop
American Airlines Logo
3:27 pm - 9:35 pmHHH-PWM
6h 08m1 stop
$403American Airlines
Find Deal
Thu, Oct 23 - Tue, Nov 11
American Airlines Logo
7:00 am - 5:27 pmPWM-HHH
10h 27m2 stops
American Airlines Logo
3:27 pm - 9:35 pmHHH-PWM
6h 08m1 stop
$408American Airlines
Find Deal
Thu, Oct 23 - Tue, Nov 11
American Airlines Logo
6:00 am - 10:46 amPWM-HHH
4h 46m1 stop
American Airlines Logo
3:32 pm - 10:48 pmHHH-PWM
7h 16m2 stops
$419American Airlines
Find Deal
Thu, Oct 9 - Tue, Oct 14
American Airlines Logo
7:00 am - 5:27 pmPWM-HHH
10h 27m2 stops
American Airlines Logo
3:27 pm - 11:38 pmHHH-PWM
8h 11m2 stops
$443American Airlines
Find Deal
Thu, Oct 23 - Tue, Nov 11

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
Sep 25
PWM7:05 amPortland
10h 45m
2 stops
HHH5:50 pmHilton Head Island
Sep 28
HHH6:20 pmHilton Head Island
5h 17m
1 stop
PWM11:37 pmPortland
$374
Find similar
American Airlines
Nov 17
PWM5:41 amPortland
5h 18m
1 stop
HHH10:59 amHilton Head Island
Nov 20
HHH11:29 amHilton Head Island
5h 10m
1 stop
PWM4:39 pmPortland
$377
Find similar
American Airlines
Oct 9
PWM6:00 amPortland
4h 46m
1 stop
HHH10:46 amHilton Head Island
Oct 14
HHH11:16 amHilton Head Island
5h 25m
1 stop
PWM4:41 pmPortland
$381
Find similar

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 August 6, 2025.
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

Thu 10/9

6:01 am-3:30 pm

2 stops9h 29m

Hilton Head Island

Tue 10/14

12:17 pm-12:05 am

2 stops11h 48m

$369

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 9/25

7:05 am-5:50 pm

2 stops10h 45m

Hilton Head Island

Sun 9/28

6:20 pm-11:37 pm

1 stop5h 17m

$374

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 11/17

5:41 am-10:59 am

1 stop5h 18m

Hilton Head Island

Thu 11/20

11:29 am-4:39 pm

1 stop5h 10m

$377

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/9

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

Tue 10/14

11:16 am-4:41 pm

1 stop5h 25m

$381

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 9/25

6:00 am-10:34 am

1 stop4h 34m

Hilton Head Island

Sun 9/28

6:20 pm-11:37 pm

1 stop5h 17m

$384

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Mon 11/17

5:41 am-2:57 pm

2 stops9h 16m

Hilton Head Island

Thu 11/20

11:29 am-4:39 pm

1 stop5h 10m

$392

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/23

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

Tue 11/11

3:27 pm-9:35 pm

1 stop6h 08m

$403

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/23

7:00 am-5:27 pm

2 stops10h 27m

Hilton Head Island

Tue 11/11

3:27 pm-9:35 pm

1 stop6h 08m

$408

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/9

6:00 am-10:46 am

1 stop4h 46m

Hilton Head Island

Tue 10/14

3:32 pm-10:48 pm

2 stops7h 16m

$419

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 10/23

7:00 am-5:27 pm

2 stops10h 27m

Hilton Head Island

Tue 11/11

3:27 pm-11:38 pm

2 stops8h 11m

$443

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 day to depart on your flight to Hilton Head Island?

The cheapest day to depart from Portland, Maine to Hilton Head Island is on a Wednesday. Travelers who choose to depart for Hilton Head Island on a Wednesday will often find tickets for as low as $419. On the other hand, Friday is the most expensive day to depart from Portland, Maine because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $685.

What is the cheapest time of day to depart on your flight to Hilton Head Island?

Flying to Hilton Head Island from Portland, Maine at noon is the least expensive time of day to depart. momondo users have found prices as low as $461 when looking at flights departing at noon. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $580 on average. Flights to Hilton Head Island from Portland, Maine in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

Best Price Found

$149

Fastest flight time

4h 34m

Direct flights

None

Airports in Hilton Head Island

1 airport
The best one-way flight to Hilton Head Island from Portland, Maine in the past 72 hours is $149. The best round-trip flight deal from Portland, Maine to Hilton Head Island found on momondo in the last 72 hours is $369.
The fastest flight from Portland, Maine to Hilton Head Island takes 4h 34m
There are no direct flights from Portland, Maine to Hilton Head Island. Popular non-direct route for this connection is Portland Airport - Hilton Head Island Airport.
There is 1 airport near Hilton Head Island: Hilton Head Island (HHH)
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  • 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 34m.

  • 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 $258Free CancellationRating
7.2
10,000 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.
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