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Hilton Head Island

$144+ Cheap flights from Portland, ME to Hilton Head Island (PWM - HHH)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
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Cheap flight deals from Portland to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 16, 2025.

Round-trip from

$269
(Delta)

One-way from

$144
(Delta)
From Portland to Hilton Head Island
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One-way flight from Portland to Hilton Head Island
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Find flight deals from Portland to Hilton Head Island

Cheapest flights from Portland to Hilton Head Island
Explore the most affordable flight options available from Portland to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2025.

This Delta deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:00 amPWM - HHH
1 stop5h 31mDelta
Tue 8/264:02 pmHHH - PWM
1 stop7h 23mDelta
Deal found 7/14$269
This American Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:00 amPWM - HHH
2 stops9h 05mAmerican Airlines
Tue 8/265:28 pmHHH - PWM
1 stop4h 33mAmerican Airlines
Deal found 7/14$274
This United Airlines deal was found by Cheapflights users on 7/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/266:00 amPWM - HHH
1 stop5h 17mUnited Airlines
Wed 7/3012:02 pmHHH - PWM
1 stop6h 24mUnited Airlines
Deal found 7/14$839

Cheapflights Fare Finder

Customize your flight search to find flights from Portland 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, Cheapflights users made 2,558,603 searches. Data last updated July 16, 2025.
Use the filters below to find and compare flights from Portland to Hilton Head Island that are best for you.

Fly from

Portland

Fly to

Hilton Head Island

Route

Depart

Return

Price

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Fri 8/22

6:00 am-11:31 am

1 stop5h 31m

Hilton Head Island

Tue 8/26

4:02 pm-11:25 pm

1 stop7h 23m

$269

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Fri 8/22

6:00 am-3:05 pm

2 stops9h 05m

Hilton Head Island

Tue 8/26

5:28 pm-10:01 pm

1 stop4h 33m

$274

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Sat 7/26

6:00 am-11:17 am

1 stop5h 17m

Hilton Head Island

Wed 7/30

12:02 pm-6:26 pm

1 stop6h 24m

$839

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Wed 7/30

6:05 am-11:23 am

1 stop5h 18m

$144

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Thu 7/31

7:23 am-4:57 pm

2 stops9h 34m

$149

PortlandHilton Head Island

PWM - HHH

PWMHHH

Portland

Tue 7/29

6:01 am-11:17 am

1 stop5h 16m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Best time to book a flight from Portland to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from Portland, Maine to Hilton Head Island?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Hilton Head Island (average of $275). Flying from Portland, Maine to Hilton Head Island in March is currently the most expensive (average of $480). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Hilton Head Island. Reviews last updated July 16, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Portland to Hilton Head Island. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,863 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Portland to Hilton Head Island. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Portland, Maine to Hilton Head Island round-trip?

    Flying on Delta is currently your cheapest option to Hilton Head Island, with prices starting at $269. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $274 and $839, respectively.

  • What are the cheapest airlines to fly from Portland, Maine to Hilton Head Island one-way?

    The cheapest airlines for a one-way flight from Portland, Maine to Hilton Head Island are Delta ($144), American Airlines ($149), and United Airlines ($174).

  • Can I find deals for flights from Portland to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Portland to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Hilton Head Island?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Hilton Head Island.

  • Can I find deals for business class flights from Portland to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Portland to Hilton Head Island by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Hilton Head Island?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Hilton Head Island (average of $275). Flying from Portland, Maine to Hilton Head Island in March is currently the most expensive (average of $480). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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

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Top airline flying from Portland to Hilton Head Island

Discover the top airline that operate flights from Portland to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$484FlexibilityNo cancel feeOn-time71%

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