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Hilton Head Island

$152+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — HHH
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$276
(American Airlines)

One-way from

$152
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$278
From Fort Myers SW Florida Intl to Hilton Head Island
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One-way flight from Fort Myers SW Florida Intl to Hilton Head Island
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High demand for flights, 9% potential price rise
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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 10/311:14 amRSW - HHH
1 stop5h 33mAmerican Airlines
Wed 10/153:32 pmHHH - RSW
1 stop7h 06mAmerican Airlines
Deal found 9/10$276
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/128:26 amRSW - HHH
1 stop6h 06mAmerican Airlines
Thu 10/165:57 pmHHH - RSW
1 stop5h 36mAmerican Airlines
Deal found 9/10$360
This American Airlines deal was found by Cheapflights users on 9/11. 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 9/2611:14 amRSW - HHH
1 stop5h 33mAmerican Airlines
Tue 9/305:20 pmHHH - RSW
1 stop5h 13mAmerican Airlines
Deal found 9/11$407
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/239:19 amRSW - HHH
1 stop5h 37mAmerican Airlines
Fri 9/263:26 pmHHH - RSW
1 stop7h 07mAmerican Airlines
Deal found 9/9$419
This American Airlines deal was found by Cheapflights users on 9/10. 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 11/256:13 amRSW - HHH
1 stop5h 36mAmerican Airlines
Mon 12/12:51 pmHHH - RSW
1 stop5h 50mAmerican Airlines
Deal found 9/10$422
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/2411:08 amRSW - HHH
1 stop3h 54mAmerican Airlines
Fri 10/3112:45 pmHHH - RSW
1 stop5h 04mAmerican Airlines
Deal found 9/11$497
This American Airlines deal was found by Cheapflights users on 9/9. 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 9/109:19 amRSW - HHH
1 stop5h 37mAmerican Airlines
Sun 9/146:20 pmHHH - RSW
1 stop5h 16mAmerican Airlines
Deal found 9/9$507
This American Airlines deal was found by Cheapflights users on 9/10. 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 10/311:14 amRSW - HHH
1 stop5h 33mAmerican Airlines
Sun 10/56:20 pmHHH - RSW
1 stop5h 16mAmerican Airlines
Deal found 9/10$570

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 September 11, 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

Fri 10/3

11:14 am-4:47 pm

1 stop5h 33m

Hilton Head Island

Wed 10/15

3:32 pm-10:38 pm

1 stop7h 06m

$276

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sun 10/12

8:26 am-2:32 pm

1 stop6h 06m

Hilton Head Island

Thu 10/16

5:57 pm-11:33 pm

1 stop5h 36m

$360

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Fri 9/26

11:14 am-4:47 pm

1 stop5h 33m

Hilton Head Island

Tue 9/30

5:20 pm-10:33 pm

1 stop5h 13m

$407

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Tue 9/23

9:19 am-2:56 pm

1 stop5h 37m

Hilton Head Island

Fri 9/26

3:26 pm-10:33 pm

1 stop7h 07m

$419

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Tue 11/25

6:13 am-11:49 am

1 stop5h 36m

Hilton Head Island

Mon 12/1

2:51 pm-8:41 pm

1 stop5h 50m

$422

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Thu 2/19

8:29 am-2:16 pm

1 stop5h 47m

Hilton Head Island

Sun 2/22

6:15 pm-12:21 am

1 stop6h 06m

$462

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Fri 10/24

11:08 am-3:02 pm

1 stop3h 54m

Hilton Head Island

Fri 10/31

12:45 pm-5:49 pm

1 stop5h 04m

$497

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Fri 10/3

11:14 am-4:47 pm

1 stop5h 33m

$152

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Wed 10/1

9:19 am-2:56 pm

1 stop5h 37m

$210

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Wed 9/17

9:19 am-2:56 pm

1 stop5h 37m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 13 results
1
2

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, January is the cheapest month in which you can book a flight from Fort Myers to Hilton Head Island (average of $275). Flying from Fort Myers 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 September 11, 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
10,000 reviews

Entertainment

6.9

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Crew

8.0

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 5h 33m. 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 31% 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, January is the cheapest month in which you can book a flight from Fort Myers to Hilton Head Island (average of $275). Flying from Fort Myers 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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Alternative routes for Fort Myers to Hilton Head Island

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$301Average$461FlexibilityNo cancel feeOn-time71%

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