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Hilton Head Island

$188+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — HHH
Mar 1 — Mar 81
Sun 3/1
Sun 3/8
1 adult, Economy
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Cheap 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 January 30, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 3/16:00 am
RSW
-
HHH
1 stop4h 33m
American Airlines
Tue 3/33:31 pm
HHH
-
RSW
1 stop4h 26m
American Airlines
Deal found 1/28$365
This American Airlines deal was found by Cheapflights users on 1/29. 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 2/1310:20 am
RSW
-
HHH
1 stop4h 02m
American Airlines
Tue 2/173:31 pm
HHH
-
RSW
1 stop4h 26m
American Airlines
Deal found 1/29$407
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Wed 3/116:00 am
RSW
-
HHH
1 stop4h 33m
American Airlines
Sun 3/152:58 pm
HHH
-
RSW
1 stop5h 44m
American Airlines
Deal found 1/28$504
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/68:40 am
RSW
-
HHH
1 stop6h 19m
American Airlines
Sun 2/83:29 pm
HHH
-
RSW
1 stop4h 30m
American Airlines
Deal found 1/28$507
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 3/192:28 pm
RSW
-
HHH
1 stop25h 13m
American Airlines
Sun 3/224:11 pm
HHH
-
RSW
1 stop16h 37m
American Airlines
Deal found 1/28$605
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 5/106:00 am
RSW
-
HHH
1 stop4h 32m
American Airlines
Sun 5/172:58 pm
HHH
-
RSW
1 stop5h 57m
American Airlines
Deal found 1/28$613
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 1/296:00 am
RSW
-
HHH
1 stop6h 20m
American Airlines
Thu 2/512:51 pm
HHH
-
RSW
1 stop7h 08m
American Airlines
Deal found 1/28$623

Find 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 January 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$327
(American Airlines)

One-way from

$188
(American Airlines)
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
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 January 30, 2026.
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

Sun 3/1

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Tue 3/3

3:31 pm-7:57 pm

1 stop4h 26m

$365

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Fri 2/13

10:20 am-2:22 pm

1 stop4h 02m

Hilton Head Island

Tue 2/17

3:31 pm-7:57 pm

1 stop4h 26m

$407

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Wed 3/11

6:00 am-10:33 am

1 stop4h 33m

Hilton Head Island

Sun 3/15

2:58 pm-8:42 pm

1 stop5h 44m

$504

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Thu 3/19

2:28 pm-3:41 pm

1 stop25h 13m

Hilton Head Island

Sun 3/22

4:11 pm-8:48 am

1 stop16h 37m

$605

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Tue 4/28

9:17 am-2:24 pm

1 stop5h 07m

$188

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sun 2/15

12:16 pm-5:44 pm

1 stop5h 28m

$279

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sat 4/11

6:00 am-10:32 am

1 stop4h 32m

$311

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Mon 4/13

11:05 am-3:20 pm

1 stop4h 15m

$350

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Tue 4/28

8:00 am-2:06 pm

2 stops30h 06m

$442

Fort MyersHilton Head Island

RSW - HHH

RSWHHH

Fort Myers SW Florida Intl

Sat 4/11

9:20 am-3:30 pm

2 stops30h 10m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Hilton Head Island flight deals on Cheapflights vs. FlightHub >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 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 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 December is currently the most expensive (average of $216). 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 January 30, 2026.
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
11,207 reviews

Crew

8.0

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,207 reviews
American Airlines
7.2
Good
11,207 reviews

Crew

8.0

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Food

6.4

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 4h 32m. 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 $306.

  • 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 December is currently the most expensive (average of $216). 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

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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 January 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$306Average$472FlexibilityNo cancel feeOn-time71%

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