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Cheap flights from Hilton Head Island to Key West from $368

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hilton Head Island to Key West departing on 4/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Hilton Head Island to Key West

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
11:03 am - 3:40 pm
HHH
-
EYW
4h 37m
1 stop
American Airlines Logo
8:20 am - 2:24 pm
EYW
-
HHH
6h 04m
1 stop
$501American Airlines
Fri, Apr 10 - Tue, Apr 14
American Airlines Logo
2:58 pm - 10:58 pm
HHH
-
EYW
8h 00m
2 stops
American Airlines Logo
8:20 am - 2:24 pm
EYW
-
HHH
6h 04m
1 stop
$506American Airlines
Fri, Apr 10 - Tue, Apr 14
American Airlines Logo
2:58 pm - 10:58 pm
HHH
-
EYW
8h 00m
2 stops
American Airlines Logo
6:45 am - 5:21 pm
EYW
-
HHH
10h 36m
2 stops
$733American Airlines
Fri, Apr 10 - Tue, Apr 14

American Airlines flights from Hilton Head Island to Key West

Our best American Airlines deals on Hilton Head Island to Key West flight tickets
American Airlines
Apr 10
HHH11:03 amHilton Head Island
4h 37m
1 stop
EYW3:40 pmKey West
Apr 14
EYW8:20 amKey West
6h 04m
1 stop
HHH2:24 pmHilton Head Island
$501
American Airlines
Apr 10
HHH2:58 pmHilton Head Island
8h 00m
2 stops
EYW10:58 pmKey West
Apr 14
EYW8:20 amKey West
6h 04m
1 stop
HHH2:24 pmHilton Head Island
$506
American Airlines
Apr 3
HHH6:15 pmHilton Head Island
4h 22m
1 stop
EYW10:37 pmKey West
Apr 7
EYW8:20 amKey West
6h 04m
1 stop
HHH2:24 pmHilton Head Island
$552

momondo Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Key West 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, momondo users made 832,500 searches. Data last updated March 30, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 4/10

11:03 am-3:40 pm

1 stop4h 37m

Key West

Tue 4/14

8:20 am-2:24 pm

1 stop6h 04m

$501

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 4/10

2:58 pm-10:58 pm

2 stops8h 00m

Key West

Tue 4/14

8:20 am-2:24 pm

1 stop6h 04m

$506

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 4/10

2:58 pm-10:58 pm

2 stops8h 00m

Key West

Tue 4/14

6:45 am-5:21 pm

2 stops10h 36m

$733
Cheapest one-way
Quickest one-way

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 4/14

12:08 pm-5:23 pm

1 stop5h 15m

$368

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 4/14

4:11 pm-2:51 pm

3 stops22h 40m

$579

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 4/14

3:05 pm-3:57 pm

2 stops24h 52m

$630

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Key West from

How to get the cheapest flight ticket from Hilton Head Island to Key West

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Hilton Head Island to Key West?

Delta and United Airlines are the most popular carriers operating from Hilton Head Island to Key West

What airlines fly to Key West?

American Airlines, Delta and Breeze Airways are the top three most popular airlines that fly to Key West from Hilton Head Island according to our data. American Airlines is the first choice among our users, with 56% of people opting to fly with this airline when traveling to Key West. Keep in mind that there are 4 different airlines that fly to Key West on a routine basis, so you have a few additional options to choose from.

When to book flights from Hilton Head Island to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Hilton Head Island to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Hilton Head Island to Key West (HHH to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilton Head Island to Key West

Fastest flight time

20h 19m

Direct flights

None
The fastest flight from Hilton Head Island to Key West takes 20h 19m
There are no direct flights from Hilton Head Island to Key West. There are no popular flight routes from Hilton Head Island to Key West.
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  • How far is Hilton Head Island to Key West by plane?

    A flight from Hilton Head Island to Key West will travel around 532.8 mi. In terms of flight time, this usually takes a little over 20h 19m.

  • When did momondo last update prices for flights from Hilton Head Island Airport to Key West Airport?

    Prices for flights from Hilton Head Island Airport to Key West Airport are updated daily.

  • How old do you have to be to fly from Hilton Head Island Airport to Key West Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hilton Head Island Airport to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

Why should I use momondo to find a flight deal from Hilton Head Island to Key West?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Hilton Head Island to Key West. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Hilton Head Island to Key West with flexible booking policies on momondo?

momondo does allow users to show only those flights to Key West from Hilton Head Island which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Hilton Head Island to Key West?

Once all potential Hilton Head Island to Key West flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Hilton Head Island to Key West right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Key West, momondo offers a useful price alert feature which will track prices for flights to Key West from Hilton Head Island and alert you when they change.

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