$132 Cheap Flights from Hilton Head Island (HHH) to Fort Myers (RSW)

View $132 flight on Sat, Oct 18, 2025Opens in a new window

Popular airlines from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)

Cheap Flights from Hilton Head Island to Fort Myers (HHH-RSW)

Prices were available within the past 7 days and start at $132 for one-way flights and $292 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Feb 24 - Wed, Mar 11
HHH
Hilton Head Island
RSW
Fort Myers
$292 Roundtrip, found 20 hours ago
$292
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Feb 24 from Hilton Head Island to Fort Myers, returning Wed, Mar 11, priced at $292 found 20 hours ago
American Airlines
Thu, Jan 15 - Sun, Jan 18
HHH
Hilton Head Island
RSW
Fort Myers
$308 Roundtrip, found 4 days ago
$308
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Jan 15 from Hilton Head Island to Fort Myers, returning Sun, Jan 18, priced at $308 found 4 days ago
American Airlines
Tue, Nov 11 - Fri, Nov 14
HHH
Hilton Head Island
RSW
Fort Myers
$312 Roundtrip, found 2 hours ago
$312
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Nov 11 from Hilton Head Island to Fort Myers, returning Fri, Nov 14, priced at $312 found 2 hours ago
American Airlines
Tue, Oct 7 - Tue, Oct 14
HHH
Hilton Head Island
RSW
Fort Myers
$337 Roundtrip, found 3 days ago
$337
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 7 from Hilton Head Island to Fort Myers, returning Tue, Oct 14, priced at $337 found 3 days ago
American Airlines
Tue, Jan 13 - Thu, Jan 15
HHH
Hilton Head Island
RSW
Fort Myers
$343 Roundtrip, found 4 days ago
$343
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jan 13 from Hilton Head Island to Fort Myers, returning Thu, Jan 15, priced at $343 found 4 days ago
American Airlines
Sun, Feb 22 - Mon, Mar 9
HHH
Hilton Head Island
RSW
Fort Myers
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Feb 22 from Hilton Head Island to Fort Myers, returning Mon, Mar 9, priced at $347 found 1 day ago
American Airlines
Mon, Jan 12 - Thu, Jan 15
HHH
Hilton Head Island
RSW
Fort Myers
$349 Roundtrip, found 4 days ago
$349
Roundtrip
found 4 days ago
Select American Airlines flight, departing Mon, Jan 12 from Hilton Head Island to Fort Myers, returning Thu, Jan 15, priced at $349 found 4 days ago
American Airlines
Tue, Feb 24 - Wed, Mar 11
HHH
Hilton Head Island
RSW
Fort Myers
$352 Roundtrip, found 20 hours ago
$352
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Feb 24 from Hilton Head Island to Fort Myers, returning Wed, Mar 11, priced at $352 found 20 hours ago
Delta
Wed, Oct 8 - Mon, Oct 20
HHH
Hilton Head Island
RSW
Fort Myers
$377 Roundtrip, found 3 days ago
$377
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Oct 8 from Hilton Head Island to Fort Myers, returning Mon, Oct 20, priced at $377 found 3 days ago
United
Wed, Oct 8 - Sat, Oct 11
HHH
Hilton Head Island
RSW
Fort Myers
$475 Roundtrip, found 3 days ago
$475
Roundtrip
found 3 days ago
Select United flight, departing Wed, Oct 8 from Hilton Head Island to Fort Myers, returning Sat, Oct 11, priced at $475 found 3 days ago
Flights from Hilton Head Island (HHH) to Fort Myers (RSW)
Origin airport
Hilton Head Island
Destination airport
Southwest Florida Intl.
Airlines serving
American Airlines
Roundtrip price
$291
Distance
398 mi

Hilton Head Island to Fort Myers Flights

The cheapest times to fly from Hilton Head Island to Fort Myers

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Hilton Head Island to Fort Myers are during the month of February. You can find some of the cheapest flights from Hilton Head Island to Fort Myers with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hilton Head Island to Fort Myers

Sunday is one of the best days to book for cheap flights from Hilton Head Island to Fort Myers: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Hilton Head Island to Fort Myers

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Hilton Head Island to Fort Myers in 2025. You can also book with separate airlines for your outbound and return journeys, from $132 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Hilton Head Island to Fort Myers flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Hilton Head Island to Fort Myers airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW) cost?
Grab a cheap one-way flight from $132 or cheap return flight from $292 from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)?
The cheapest month to fly from HHH to RSW is February, when demand is low. Off-peak season is usually when better flight deals are available between these airports.
Which airlines fly direct from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)?
You can't catch a direct flight from Hilton Head Island, SC (HHH) to Southwest Florida Intl. Airport (RSW). However, you can arrive in Fort Myers without any layovers by departing from Charleston Intl. Airport (CHS).
What is the cheapest airline that flies from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Tailor the search to your trip, then sort by "Price (lowest to highest)" to find the carrier with the cheapest HHH to RSW flight.
How many flights per day from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)?
You'll need to take a flight with a layover if you're traveling from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW). Direct flights don't operate daily on this route. However, just filter your search to include one or two stops to discover the best option for your trip.
What day of the week has the most flights from HHH to RSW?
You'll usually find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)?
To land at Southwest Florida Intl. Airport (RSW) on time, pick a flight that leaves Hilton Head Island Airport (HHH) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW) last-minute?
Last-minute fares from HHH to RSW are usually more expensive. To lock in the lowest prices, start looking for flights as soon as possible. That being said, if you're flexible with your travel plans, it's possible to land a cheap ticket just before your departure.
Is it cheaper to book a HHH to RSW flight and hotel package?
Compared with arranging flights and hotels separately, booking a HHH to RSW flight and hotel package with Expedia could result in significant savings. Better yet, having everything in one convenient place will take the stress out of travel planning. Just pick your flights and choose from our wide range of stays, then customize your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from Hilton Head Island Airport (HHH) to Southwest Florida Intl. Airport (RSW)?
In most cases, you're able to cancel or reschedule your HHH to RSW flight. However, there may be additional fees, especially if you made your booking over 24 hours ago. Double-check your itinerary for the airline's fees and policies on flight changes, or if you want more details, visit our Customer Service portal.

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*Available to One Key members.