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Cheap flights from Hilton Head Island to Key West from $308

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 9/30. 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
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
10:55 am - 11:48 am
HHH
-
EYW
24h 53m
1 stop
American Airlines Logo
5:19 pm - 10:37 am
EYW
-
HHH
17h 18m
1 stop
$704American Airlines
Sat, Jul 11 - Sat, Jul 18
American Airlines Logo
10:55 am - 11:48 am
HHH
-
EYW
24h 53m
1 stop
American Airlines Logo
5:19 pm - 11:17 am
EYW
-
HHH
17h 58m
2 stops
$709American Airlines
Sat, Jul 11 - Sat, Jul 18
American Airlines Logo
11:07 am - 11:48 am
HHH
-
EYW
24h 41m
1 stop
American Airlines Logo
7:33 pm - 10:25 am
EYW
-
HHH
14h 52m
2 stops
$734American Airlines
Mon, Jul 20 - Fri, Jul 31
American Airlines Logo
4:55 pm - 11:48 am
HHH
-
EYW
18h 53m
2 stops
American Airlines Logo
7:33 pm - 10:25 am
EYW
-
HHH
14h 52m
2 stops
$739American Airlines
Mon, Jul 20 - Fri, Jul 31
American Airlines Logo
11:07 am - 11:48 am
HHH
-
EYW
24h 41m
1 stop
American Airlines Logo
5:34 pm - 11:44 am
EYW
-
HHH
18h 10m
1 stop
$767American Airlines
Mon, Jul 20 - Fri, Jul 31
American Airlines Logo
5:38 pm - 10:55 am
HHH
-
EYW
17h 17m
2 stops
American Airlines Logo
7:55 pm - 11:17 am
EYW
-
HHH
15h 22m
2 stops
$770American Airlines
Sat, Jul 11 - Sat, Jul 18
American Airlines Logo
5:38 pm - 1:14 pm
HHH
-
EYW
19h 36m
2 stops
American Airlines Logo
7:55 pm - 11:17 am
EYW
-
HHH
15h 22m
2 stops
$789American Airlines
Sat, Jul 11 - Sat, Jul 18
American Airlines Logo
10:57 am - 11:40 am
HHH
-
EYW
24h 43m
1 stop
American Airlines Logo
7:29 pm - 10:27 am
EYW
-
HHH
14h 58m
2 stops
$800American Airlines
Fri, May 29 - Tue, Jun 2
American Airlines Logo
5:21 pm - 11:40 am
HHH
-
EYW
18h 19m
2 stops
American Airlines Logo
7:29 pm - 10:27 am
EYW
-
HHH
14h 58m
2 stops
$806American Airlines
Fri, May 29 - Tue, Jun 2
American Airlines Logo
2:43 pm - 11:01 am
HHH
-
EYW
20h 18m
2 stops
American Airlines Logo
7:40 pm - 11:10 am
EYW
-
HHH
15h 30m
2 stops
$812American Airlines
Fri, May 29 - Mon, Jun 1

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
Jul 11
HHH10:55 amHilton Head Island
24h 53m
1 stop
EYW11:48 amKey West
Jul 18
EYW5:19 pmKey West
17h 18m
1 stop
HHH10:37 amHilton Head Island
$704
American Airlines
Jul 11
HHH10:55 amHilton Head Island
24h 53m
1 stop
EYW11:48 amKey West
Jul 18
EYW5:19 pmKey West
17h 58m
2 stops
HHH11:17 amHilton Head Island
$709
American Airlines
Jul 20
HHH11:07 amHilton Head Island
24h 41m
1 stop
EYW11:48 amKey West
Jul 31
EYW7:33 pmKey West
14h 52m
2 stops
HHH10:25 amHilton Head Island
$734

United Airlines flights from Hilton Head Island to Key West

Our best United Airlines deals on Hilton Head Island to Key West flight tickets
United Airlines
Aug 22
HHH2:48 pmHilton Head Island
22h 41m
2 stops
EYW1:29 pmKey West
Aug 26
EYW2:20 pmKey West
23h 43m
2 stops
HHH2:03 pmHilton Head Island
$1,537
United Airlines
Aug 22
HHH2:48 pmHilton Head Island
22h 41m
2 stops
EYW1:29 pmKey West
Aug 26
EYW2:20 pmKey West
23h 43m
2 stops
HHH2:03 pmHilton Head Island
$1,571
United Airlines
Aug 22
HHH1:50 pmHilton Head Island
23h 39m
1 stop
EYW1:29 pmKey West
Aug 26
EYW2:20 pmKey West
23h 43m
2 stops
HHH2:03 pmHilton Head Island
$1,618

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 May 14, 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

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Sat 7/11

10:55 am-11:48 am

1 stop24h 53m

Key West

Sat 7/18

5:19 pm-10:37 am

1 stop17h 18m

$704

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Sat 7/11

10:55 am-11:48 am

1 stop24h 53m

Key West

Sat 7/18

5:19 pm-11:17 am

2 stops17h 58m

$709

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 7/20

11:07 am-11:48 am

1 stop24h 41m

Key West

Fri 7/31

7:33 pm-10:25 am

2 stops14h 52m

$734

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 7/20

4:55 pm-11:48 am

2 stops18h 53m

Key West

Fri 7/31

7:33 pm-10:25 am

2 stops14h 52m

$739

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 7/20

11:07 am-11:48 am

1 stop24h 41m

Key West

Fri 7/31

5:34 pm-11:44 am

1 stop18h 10m

$767
Quickest round-trip

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Sat 7/11

5:38 pm-10:55 am

2 stops17h 17m

Key West

Sat 7/18

7:55 pm-11:17 am

2 stops15h 22m

$770

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Sat 7/11

5:38 pm-1:14 pm

2 stops19h 36m

Key West

Sat 7/18

7:55 pm-11:17 am

2 stops15h 22m

$789

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 5/29

10:57 am-11:40 am

1 stop24h 43m

Key West

Tue 6/2

7:29 pm-10:27 am

2 stops14h 58m

$800

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 5/29

5:21 pm-11:40 am

2 stops18h 19m

Key West

Tue 6/2

7:29 pm-10:27 am

2 stops14h 58m

$806

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 5/29

2:43 pm-11:01 am

2 stops20h 18m

Key West

Mon 6/1

7:40 pm-11:10 am

2 stops15h 30m

$812

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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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, American Airlines, 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 53% 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

22h 41m

Direct flights

None
The fastest flight from Hilton Head Island to Key West takes 22h 41m
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.
Search flight deals

Frequently asked questions about flying from Hilton Head Island to Key West

  • 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 22h 41m.

  • 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.

An easier way to manage your Key West trip

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