HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilton Head Island

$259+ Cheap flights from Portland, ME to Hilton Head Island (PWM - HHH)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — HHH
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Hilton Head Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 June 12, 2025.

Round-trip from

$259
(American Airlines)
From Portland to Hilton Head Island
Search Deals

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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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 7/47:41 amPWM - HHH
1 stop4h 46mAmerican Airlines
Mon 7/71:16 pmHHH - PWM
1 stop7h 14mAmerican Airlines
Deal found 6/12$259
This Delta deal was found by Cheapflights users on 6/12. 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 6/136:03 amPWM - HHH
1 stop5h 16mDelta
Mon 6/163:58 pmHHH - PWM
1 stop7h 32mDelta
Deal found 6/12$389

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 June 12, 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 7/4

7:41 am-12:27 pm

1 stop4h 46m

Hilton Head Island

Mon 7/7

1:16 pm-8:30 pm

1 stop7h 14m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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 $479). 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.

Rainfall in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

Temperature in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hilton Head Island, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

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 June 12, 2025.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Food

6.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Food

6.5

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break

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 is the cheapest airline to fly from Portland, Maine to Hilton Head Island round-trip?

    Flying on American Airlines is currently your cheapest option to Hilton Head Island, with prices starting at $259.

  • 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 $479). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Beaufort
Bluffton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Charlotte flights
Boston to Charleston flights
Boston to Myrtle Beach flights
Boston to Savannah flights
Boston to Greenville flights
Portland to Charlotte flights
Boston to Columbia flights
Boston to Hilton Head Island flights
Portland to Savannah flights
Boston to Augusta flights
Portland to Myrtle Beach flights
Portland to Charleston flights
Portland to Greenville flights
Bangor to Charlotte flights
Bangor to Savannah flights
Portland to Columbia flights
Bangor to Greenville flights
Bangor to Myrtle Beach flights
Portland to Augusta flights
Augusta to Charlotte flights
Boston to Florence flights
Bangor to Charleston flights
Rockland to Charlotte flights
Portland to Florence flights
Augusta to Charleston flights
Rockland to Charleston flights

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$486FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.