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Cheap flights from Hilton Head Island to Portland from $171

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hilton Head Island to Portland departing on 9/1. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Hilton Head Island to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:08 pm - 10:36 pmHHH  Hilton Head Island-PWM Portland
4h 28m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 11:05 amPWM  Portland-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
$329American Airlines
Fri, Oct 9 - Mon, Oct 12
American Airlines Logo
5:54 pm - 10:33 pmHHH  Hilton Head Island-PWM Portland
4h 39m1 stop Charlotte Douglas
American Airlines Logo
7:10 am - 11:58 amPWM  Portland-HHH Hilton Head Island
4h 48m1 stop Charlotte Douglas
$329American Airlines
Fri, Nov 6 - Sat, Nov 14
United Airlines Logo
2:58 pm - 11:59 pmHHH  Hilton Head Island-PWM Portland
9h 01m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
United Airlines Logo
6:00 am - 1:05 pmPWM  Portland-HHH Hilton Head Island
7h 05m1 stop Newark
$384United Airlines
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
10:57 am - 4:33 pmHHH  Hilton Head Island-PWM Portland
5h 36m1 stop Washington, D.C. Reagan-National
American Airlines Logo
6:02 am - 10:27 amPWM  Portland-HHH Hilton Head Island
4h 25m1 stop Washington, D.C. Reagan-National
$395American Airlines
Tue, Aug 25 - Sat, Aug 29
American Airlines Logo
6:13 pm - 10:36 pmHHH  Hilton Head Island-PWM Portland
4h 23m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 11:05 amPWM  Portland-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
$419American Airlines
Sat, Oct 10 - Mon, Oct 12
American Airlines Logo
2:56 pm - 10:36 pmHHH  Hilton Head Island-PWM Portland
7h 40m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 11:05 amPWM  Portland-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
$419American Airlines
Wed, Oct 7 - Mon, Oct 12
American Airlines Logo
6:08 pm - 10:36 pmHHH  Hilton Head Island-PWM Portland
4h 28m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 11:05 amPWM  Portland-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
$419American Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
5:54 pm - 10:33 pmHHH  Hilton Head Island-PWM Portland
4h 39m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 3:47 pmPWM  Portland-HHH Hilton Head Island
9h 47m2 stops Philadelphia Charlotte Douglas
$433American Airlines
Fri, Nov 6 - Sat, Nov 14
United Airlines Logo
2:58 pm - 11:59 pmHHH  Hilton Head Island-PWM Portland
9h 01m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
United Airlines Logo
6:03 am - 2:03 pmPWM  Portland-HHH Hilton Head Island
8h 00m1 stop Chicago O'Hare Intl
$449United Airlines
Fri, Aug 28 - Mon, Aug 31
United Airlines Logo
2:58 pm - 11:59 pmHHH  Hilton Head Island-PWM Portland
9h 01m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
United Airlines Logo
5:15 am - 2:03 pmPWM  Portland-HHH Hilton Head Island
8h 48m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
$469United Airlines
Fri, Aug 28 - Mon, Aug 31

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United Airlines flights from Hilton Head Island to Portland, Maine

Our best United Airlines deals on Hilton Head Island to Portland, Maine flight tickets
United Airlines
Aug 25
HHH2:58 pmHilton Head Island
9h 01m
2 stops
PWM11:59 pmPortland
Aug 29
PWM6:00 amPortland
7h 05m
1 stop
HHH1:05 pmHilton Head Island
$384
United Airlines
Aug 28
HHH2:58 pmHilton Head Island
9h 01m
2 stops
PWM11:59 pmPortland
Aug 31
PWM6:03 amPortland
8h 00m
1 stop
HHH2:03 pmHilton Head Island
$449
United Airlines
Aug 28
HHH2:58 pmHilton Head Island
9h 01m
2 stops
PWM11:59 pmPortland
Aug 31
PWM5:15 amPortland
8h 48m
2 stops
HHH2:03 pmHilton Head Island
$469

American Airlines flights from Hilton Head Island to Portland, Maine

Our best American Airlines deals on Hilton Head Island to Portland, Maine flight tickets
American Airlines
Oct 9
HHH6:08 pmHilton Head Island
4h 28m
1 stop
PWM10:36 pmPortland
Oct 12
PWM6:00 amPortland
5h 05m
1 stop
HHH11:05 amHilton Head Island
$329
American Airlines
Aug 25
HHH10:57 amHilton Head Island
5h 36m
1 stop
PWM4:33 pmPortland
Aug 29
PWM6:02 amPortland
4h 25m
1 stop
HHH10:27 amHilton Head Island
$395
American Airlines
Oct 7
HHH2:56 pmHilton Head Island
7h 40m
1 stop
PWM10:36 pmPortland
Oct 12
PWM6:00 amPortland
5h 05m
1 stop
HHH11:05 amHilton Head Island
$419

momondo Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Portland, Maine 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 13, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Fri 10/9

6:08 pm-10:36 pm

1 stop4h 28m

Portland

Mon 10/12

6:00 am-11:05 am

1 stop5h 05m

$329
Quickest round-trip

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Fri 11/6

5:54 pm-10:33 pm

1 stop4h 39m

Portland

Sat 11/14

7:10 am-11:58 am

1 stop4h 48m

$329

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Tue 8/25

2:58 pm-11:59 pm

2 stops9h 01m

Portland

Sat 8/29

6:00 am-1:05 pm

1 stop7h 05m

$384

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Tue 8/25

10:57 am-4:33 pm

1 stop5h 36m

Portland

Sat 8/29

6:02 am-10:27 am

1 stop4h 25m

$395

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Sat 10/10

6:13 pm-10:36 pm

1 stop4h 23m

Portland

Mon 10/12

6:00 am-11:05 am

1 stop5h 05m

$419

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Wed 10/7

2:56 pm-10:36 pm

1 stop7h 40m

Portland

Mon 10/12

6:00 am-11:05 am

1 stop5h 05m

$419

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Thu 10/8

6:08 pm-10:36 pm

1 stop4h 28m

Portland

Mon 10/12

6:00 am-11:05 am

1 stop5h 05m

$419

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Fri 11/6

5:54 pm-10:33 pm

1 stop4h 39m

Portland

Sat 11/14

6:00 am-3:47 pm

2 stops9h 47m

$433

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Fri 8/28

2:58 pm-11:59 pm

2 stops9h 01m

Portland

Mon 8/31

6:03 am-2:03 pm

1 stop8h 00m

$449

Hilton Head IslandPortland

HHH Hilton Head Island - PWM Portland

HHHPWM

Hilton Head Island

Fri 8/28

2:58 pm-11:59 pm

2 stops9h 01m

Portland

Mon 8/31

5:15 am-2:03 pm

2 stops8h 48m

$469

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Portland from

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

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 Hilton Head Island to Portland?

Delta, United Airlines, and American Airlines are the most popular carriers operating from Hilton Head Island to Portland

What airlines fly to Portland, Maine?

JetBlue, Delta and American Airlines are the top three most popular airlines that fly to Portland, Maine from Hilton Head Island according to our data. JetBlue is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 7 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

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

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

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

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

Fastest flight time

4h 39m

Direct flights

None
The fastest flight from Hilton Head Island to Portland, Maine takes 4h 39m
There are no direct flights from Hilton Head Island to Portland, Maine. There are no popular flight routes from Hilton Head Island to Portland, Maine.
Search flight deals

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

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

    There are 973.5 mi between Hilton Head Island and Portland. By plane, this route typically takes 4h 39m.

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hilton Head Island Airport to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The travel and health documents required for your trip to Portland 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 Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Lewiston
Brunswick
Freeport
Gorham
Auburn
Bartlett
Conway
Windham
Bath
Intervale
Oxford
Georgetown
Falmouth
Tamworth

Why use momondo?

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

It is quick and easy to find Hilton Head Island to Portland flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Portland that suits you.

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

momondo does allow users to show only those flights to Portland from Hilton Head Island which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Hilton Head Island to Portland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Portland from Hilton Head Island are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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