$279+ Cheap flights from Portland to Hilton Head Island (PDX - 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — HHH
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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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
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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
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Best
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Cheapest flights from Portland to Hilton Head IslandExplore 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 10, 2026.
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 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 10/1910:44 pm
PDX
- HHH
1 stop8h 29m
American Airlines
Tue 10/273:58 pm
HHH
- PDX
1 stop7h 28m
American Airlines
Deal found 6/8![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/85:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Tue 7/144:55 pm
HHH
- PDX
1 stop10h 00m
American Airlines
Deal found 6/8![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 6/7. 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.
Sat 10/2410:55 pm
PDX
- HHH
2 stops13h 24m
Delta
Wed 10/2812:00 pm
HHH
- PDX
2 stops10h 58m
Delta
Deal found 6/7![Delta logo]()
$460
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/810:40 pm
PDX
- HHH
2 stops11h 12m
United Airlines
Tue 7/143:05 pm
HHH
- PDX
2 stops12h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$579
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Sat 8/111:43 pm
PDX
- HHH
2 stops11h 33m
American Airlines
Sun 8/24:55 pm
HHH
- PDX
1 stop10h 00m
American Airlines
Deal found 6/8![American Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/315:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Fri 8/73:27 pm
HHH
- PDX
2 stops10h 42m
American Airlines
Deal found 6/8![American Airlines logo]()
$602
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/315:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Sat 8/83:27 pm
HHH
- PDX
2 stops11h 32m
American Airlines
Deal found 6/8![American Airlines logo]()
$608
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 6/1210:52 pm
PDX
- HHH
1 stop11h 07m
United Airlines
Sun 6/143:05 pm
HHH
- PDX
1 stop10h 24m
United Airlines
Deal found 6/8![United Airlines logo]()
$639
This American Airlines deal was found by Cheapflights users on 6/8. 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 10/203:49 pm
PDX
- HHH
2 stops15h 24m
American Airlines
Tue 10/2712:35 pm
HHH
- PDX
2 stops13h 29m
American Airlines
Deal found 6/8![American Airlines logo]()
$649
Best flights from Portland to Hilton Head IslandDiscover carefully curated flight deals from Portland to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
Discover carefully curated flight deals from Portland to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/7. 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.
Sat 10/243:49 pm
PDX
- HHH
2 stops15h 24m
American Airlines
Wed 10/283:58 pm
HHH
- PDX
1 stop7h 28m
American Airlines
Deal found 6/7![American Airlines logo]()
$514
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/810:40 pm
PDX
- HHH
2 stops11h 12m
United Airlines
Tue 7/143:05 pm
HHH
- PDX
2 stops12h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$579
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Mon 10/1910:44 pm
PDX
- HHH
1 stop8h 29m
American Airlines
Tue 10/2712:35 pm
HHH
- PDX
2 stops13h 29m
American Airlines
Deal found 6/8![American Airlines logo]()
$514
This American Airlines deal was found by Cheapflights users on 6/8. 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 10/203:49 pm
PDX
- HHH
2 stops15h 24m
American Airlines
Tue 10/273:58 pm
HHH
- PDX
1 stop7h 28m
American Airlines
Deal found 6/8![American Airlines logo]()
$514
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Thu 9/1711:17 pm
PDX
- HHH
1 stop10h 42m
United Airlines
Mon 9/211:50 pm
HHH
- PDX
1 stop11h 13m
United Airlines
Deal found 6/7![United Airlines logo]()
$673
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/315:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Fri 8/73:27 pm
HHH
- PDX
2 stops10h 42m
American Airlines
Deal found 6/8![American Airlines logo]()
$602
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 7/310:52 pm
PDX
- HHH
1 stop11h 10m
United Airlines
Mon 7/63:05 pm
HHH
- PDX
2 stops33h 10m
United Airlines
Deal found 6/8![United Airlines logo]()
$760
This Delta deal was found by Cheapflights users on 6/7. 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.
Wed 9/1612:20 am
PDX
- HHH
2 stops12h 07m
Delta
Mon 9/2112:15 pm
HHH
- PDX
1 stop9h 44m
Delta
Deal found 6/7![Delta logo]()
$2,073
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Wed 7/110:52 pm
PDX
- HHH
1 stop11h 00m
United Airlines
Sun 7/51:45 pm
HHH
- PDX
1 stop11h 03m
United Airlines
Deal found 6/7![United Airlines logo]()
$2,479
Last-minute flights from Portland to Hilton Head IslandDiscover last-minute flight deals from Portland to Hilton Head Island. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Hilton Head Island. Data last updated June 10, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 6/1210:52 pm
PDX
- HHH
1 stop11h 07m
United Airlines
Sun 6/143:05 pm
HHH
- PDX
1 stop10h 24m
United Airlines
Deal found 6/8![United Airlines logo]()
$639
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/310:57 pm
PDX
- HHH
1 stop11h 24m
American Airlines
Mon 7/62:03 pm
HHH
- PDX
1 stop13h 47m
American Airlines
Deal found 6/8![American Airlines logo]()
$676
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 7/310:52 pm
PDX
- HHH
1 stop11h 10m
United Airlines
Mon 7/63:05 pm
HHH
- PDX
2 stops33h 10m
United Airlines
Deal found 6/8![United Airlines logo]()
$760
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/85:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Tue 7/144:55 pm
HHH
- PDX
1 stop10h 00m
American Airlines
Deal found 6/8![American Airlines logo]()
$404
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Wed 7/810:40 pm
PDX
- HHH
2 stops11h 12m
United Airlines
Tue 7/143:05 pm
HHH
- PDX
2 stops12h 45m
United Airlines
Deal found 6/8![United Airlines logo]()
$579
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/315:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Fri 8/73:27 pm
HHH
- PDX
2 stops10h 42m
American Airlines
Deal found 6/8![American Airlines logo]()
$602
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/315:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Sat 8/83:27 pm
HHH
- PDX
2 stops11h 32m
American Airlines
Deal found 6/8![American Airlines logo]()
$608
One-way flights from Portland to Hilton Head IslandSearch for one-way flight options from Portland to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
Search for one-way flight options from Portland to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/8. 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 7/315:49 am
PDX
- HHH
1 stop7h 36m
American Airlines
Deal found 6/8![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 6/8. 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 8/110:52 pm
PDX
- HHH
1 stop11h 00m
United Airlines
Deal found 6/8![United Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 7/314:15 pm
PDX
- HHH
3 stops19h 06m
United Airlines
Deal found 6/8![United Airlines logo]()
$1,062
Find flight deals from Portland to Hilton Head Island
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) 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 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $379 (American Airlines) |
One-way from | $279 (American Airlines) |
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 10, 2026.
Use the filters below to find and compare flights from Portland to Hilton Head Island that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Sat 10/24
3:49 pm-10:13 am
2 stops15h 24m
Hilton Head Island
Wed 10/28
3:58 pm-8:26 pm
1 stop7h 28m
$514
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Mon 10/19
10:44 pm-10:13 am
1 stop8h 29m
Hilton Head Island
Tue 10/27
12:35 pm-11:04 pm
2 stops13h 29m
$514
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Tue 10/20
3:49 pm-10:13 am
2 stops15h 24m
Hilton Head Island
Tue 10/27
3:58 pm-8:26 pm
1 stop7h 28m
$514
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Wed 7/8
10:40 pm-12:52 pm
2 stops11h 12m
Hilton Head Island
Tue 7/14
3:05 pm-12:50 am
2 stops12h 45m
$579
Quickest round-trip
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Fri 7/31
5:49 am-4:25 pm
1 stop7h 36m
Hilton Head Island
Fri 8/7
3:27 pm-11:09 pm
2 stops10h 42m
$602
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Thu 9/17
11:17 pm-12:59 pm
1 stop10h 42m
Hilton Head Island
Mon 9/21
1:50 pm-10:03 pm
1 stop11h 13m
$673
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Fri 7/3
10:52 pm-1:02 pm
1 stop11h 10m
Hilton Head Island
Mon 7/6
3:05 pm-9:15 pm
2 stops33h 10m
$760
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Wed 9/16
12:20 am-3:27 pm
2 stops12h 07m
Hilton Head Island
Mon 9/21
12:15 pm-6:59 pm
1 stop9h 44m
$2,073
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Wed 7/1
10:52 pm-12:52 pm
1 stop11h 00m
Hilton Head Island
Sun 7/5
1:45 pm-9:48 pm
1 stop11h 03m
$2,479
Cheapest one-way
Quickest one-way
PortlandHilton Head Island
PDX - HHH
PDXHHH
Portland
Sat 8/1
10:52 pm-12:52 pm
1 stop11h 00m
$279
Showing 1-10 of 11 resultsSorted by cheapest first
Compare providers for flights from Portland to Hilton Head Island
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Hilton Head Island in June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Hilton Head Island flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
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.
PDX-HHH
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.
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 10, 2026.
Read through reviews of airlines operating flights from Portland to Hilton Head Island, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Overall
7.1
Boarding
7.5
Crew
7.9
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
Food
6.4
Overall
7.1
Boarding
7.5
Crew
7.9
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Apr 2026
DFW - BDL
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.
Traveling to a place near Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsBeaufort
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Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
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Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
Portland and Hilton Head Island flights
Browse other Portland and Hilton Head Island flight options. Last updated on June 10, 2026.
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Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on June 10, 2026.
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Check out other popular destinations found by fellow travelers in 2026
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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$367 | Average$520 | FlexibilityNo cancel fee | On-time71% |