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Hilton Head Island

$159+ Cheap flights from Fort Myers to Hilton Head Island (RSW - 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — HHH
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Fort Myers to Hilton Head Island

Cheapest flights from Fort Myers to Hilton Head Island
Explore the most affordable flight options available from Fort Myers to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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 11/128:40 amRSW - HHH
1 stop6h 17mAmerican Airlines
Sun 11/166:40 pmHHH - RSW
1 stop5h 47mAmerican Airlines
Deal found 10/27$479
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/107:01 amRSW - HHH
1 stop5h 28mAmerican Airlines
Thu 11/1312:19 pmHHH - RSW
1 stop4h 11mAmerican Airlines
Deal found 10/30$636
This American Airlines deal was found by Cheapflights users on 10/28. 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 10/3111:08 amRSW - HHH
1 stop3h 54mAmerican Airlines
Sun 11/26:40 pmHHH - RSW
1 stop5h 47mAmerican Airlines
Deal found 10/28$763

Cheap flight deals from Fort Myers to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$382
(American Airlines)

One-way from

$159
(American Airlines)

Popular in

December

Cheapest in

September
Provider with most accurate pricing for Fort Myers SW Florida Intl-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Hilton Head Island flights.
Search Deals
From Fort Myers SW Florida Intl to Hilton Head Island
Search Deals
One-way flight from Fort Myers SW Florida Intl to Hilton Head Island
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High demand for flights, 5% potential price rise
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 potential savings vs. average RT price).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Fort Myers 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 October 30, 2025.
Use the filters below to find and compare flights from Fort Myers to Hilton Head Island that are best for you.

Fly from

Fort Myers

Fly to

Hilton Head Island

Route

Depart

Return

Price

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Wed 11/12

8:40 am-2:57 pm

1 stop6h 17m

Hilton Head Island

Sun 11/16

6:40 pm-12:27 am

1 stop5h 47m

$479

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Mon 11/10

7:01 am-12:29 pm

1 stop5h 28m

Hilton Head Island

Thu 11/13

12:19 pm-4:30 pm

1 stop4h 11m

$636

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sat 12/13

8:04 am-1:47 pm

1 stop5h 43m

$189

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Tue 12/9

1:24 pm-6:33 pm

1 stop5h 09m

$189

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Mon 12/8

7:16 am-12:22 pm

1 stop5h 06m

$189

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Thu 12/11

8:04 am-1:47 pm

1 stop5h 43m

$189

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sun 12/21

8:10 am-2:16 pm

1 stop6h 06m

$194

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sun 12/7

8:04 am-1:47 pm

1 stop5h 43m

$224

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Fri 12/12

2:59 pm-1:47 pm

2 stops22h 48m

$239

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Wed 12/10

2:59 pm-11:51 am

2 stops20h 52m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 11 results
1
2

Compare providers for flights from Fort Myers 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 Fort Myers to Hilton Head Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Fort Myers-Hilton Head Island flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Fort Myers-Hilton Head Island flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Fort Myers-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Hilton Head Island flights, Cheapflights users trust eDreams the most. eDreams 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 Fort Myers-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 Fort Myers to Hilton Head Island

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

What is the cheapest month to book a flight from Fort Myers to Hilton Head Island?

Currently, September is the cheapest month in which you can book a flight from Fort Myers to Hilton Head Island (average of $62). Flying from Fort Myers to Hilton Head Island in March is currently the most expensive (average of $125). 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 October 30, 2025.
See what other customers who have flown with American Airlines from Fort Myers to Hilton Head Island have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,034 reviews

Boarding

7.5

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Boarding

7.5

Food

6.4

Overall

7.2

Comfort

7.2

Crew

8.0

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers 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.

  • How long is the flight from Fort Myers to Hilton Head Island?

    American Airlines can get you from Fort Myers to Hilton Head Island in just under 6h 17m. Your travel time can differ by up to . The distance from Fort Myers to Hilton Head Island is about 398 mi.

  • What is the cheapest airline to fly from Fort Myers to Hilton Head Island round-trip?

    Cheapflights users have booked flights from Fort Myers to Hilton Head Island round-trip from $301. You may be able to fly from Fort Myers to Hilton Head Island for 29% less than the average price by searching for this airline.

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

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

  • How can I find direct flights from Fort Myers 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 Fort Myers to Hilton Head Island.

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

    Yes. Cheapflights offers flight deals from Fort Myers 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 Fort Myers to Hilton Head Island?

    Currently, September is the cheapest month in which you can book a flight from Fort Myers to Hilton Head Island (average of $62). Flying from Fort Myers to Hilton Head Island in March is currently the most expensive (average of $125). 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 Fort Myers to Hilton Head Island

Discover the top airline that operate flights from Fort Myers 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$301Average$461FlexibilityNo cancel feeOn-time71%

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