HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$289+ Cheap flights from Hilton Head Island to Portland, ME (HHH - PWM)

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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — PWM
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hilton Head Island to Portland 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 Hilton Head Island to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Portland (PWM). 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 April 24, 2025.

Round-trip from

$289
(Delta)

Popular in

June

Cheapest in

April

Average price

$208
From Hilton Head Island to Portland
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

Find flight deals from Hilton Head Island to Portland

Cheapest flights from Hilton Head Island to Portland
Explore the most affordable flight options available from Hilton Head Island to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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.
Thu 5/84:00 pmHHH - PWM
1 stop7h 21mDelta
Mon 5/126:05 amPWM - HHH
1 stop5h 16mDelta
Deal found 4/23$289
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Tue 6/174:42 pmHHH - PWM
1 stop7h 17mAmerican Airlines
Sat 6/215:30 amPWM - HHH
1 stop10h 18mAmerican Airlines
Deal found 4/24$442

Cheapflights Fare Finder

Customize your flight search to find flights from Hilton Head Island to Portland 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 April 24, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Portland that are best for you.

Fly from

Hilton Head Island

Fly to

Portland

Route

Depart

Return

Price

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Thu 5/8

4:00 pm-11:21 pm

1 stop7h 21m

Portland

Mon 5/12

6:05 am-11:21 am

1 stop5h 16m

$289

Hilton Head IslandPortland

HHH - PWM

HHHPWM

Hilton Head Island

Tue 6/17

4:42 pm-11:59 pm

1 stop7h 17m

Portland

Sat 6/21

5:30 am-3:48 pm

1 stop10h 18m

$442

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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

Have a flexible travel schedule? Discover the best time to fly to Portland from Hilton Head Island 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 Hilton Head Island to Portland

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

Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Portland, Maine (average of $296). Flying from Hilton Head Island to Portland, Maine in May is currently the most expensive (average of $416). 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.

What is the cheapest time of day to fly from HHH to PWM?

Find hourly flight availability from Hilton Head Island to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 24, 2025.

It’s typically best to fly out from Hilton Head Island to Portland, Maine at noon. Doing so could potentially save you 13% on the flight price compared to flying in the morning, which is usually more expensive.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated April 24, 2025.
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

8.0

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Portland. 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 Hilton Head Island to Portland, Maine round-trip?

    Delta, at $289, was found to be the cheapest airline from Hilton Head Island to Portland, Maine. An alternate airline flying to your destination would be American Airlines. Delta is priced at 18% lower than the current average price of a flight leaving 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hilton Head Island to Portland 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 Hilton Head Island to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Hilton Head Island to Portland, Maine (average of $296). Flying from Hilton Head Island to Portland, Maine in May is currently the most expensive (average of $416). 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
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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 Hilton Head Island to Portland

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

Top airline flying from Hilton Head Island to Portland

Discover the top airline that operate flights from Hilton Head Island to Portland. 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$243Average$337FlexibilityNo 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.