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Cheap flights from Hilton Head Island to Key West from $811

This is the cheapest round-trip 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 9/3. 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

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
3:27 pm - 10:56 amHHH  Hilton Head Island-EYW Key West
19h 29m2 stops Charlotte Douglas Miami
American Airlines Logo
7:47 pm - 1:45 pmEYW  Key West-HHH Hilton Head Island
17h 58m2 stops Miami Charlotte Douglas
$811American Airlines
Thu, Sep 3 - Thu, Sep 10
American Airlines Logo
5:16 pm - 1:05 pmHHH  Hilton Head Island-EYW Key West
19h 49m2 stops Charlotte Douglas Miami
American Airlines Logo
1:40 pm - 11:09 amEYW  Key West-HHH Hilton Head Island
21h 29m2 stops Miami Charlotte Douglas
$853American Airlines
Fri, Aug 21 - Tue, Aug 25
American Airlines Logo
5:54 pm - 9:48 amHHH  Hilton Head Island-EYW Key West
15h 54m2 stops Charlotte Douglas Miami
American Airlines Logo
7:57 pm - 5:07 pmEYW  Key West-HHH Hilton Head Island
21h 10m2 stops Miami Charlotte Douglas
$864American Airlines
Mon, Nov 23 - Fri, Nov 27
American Airlines Logo
11:40 am - 4:18 pmHHH  Hilton Head Island-EYW Key West
4h 38m1 stop Charlotte Douglas
American Airlines Logo
4:56 pm - 1:17 pmEYW  Key West-HHH Hilton Head Island
20h 21m1 stop Chicago O'Hare Intl
$869American Airlines
Fri, Aug 21 - Tue, Aug 25
American Airlines Logo
11:40 am - 4:18 pmHHH  Hilton Head Island-EYW Key West
4h 38m1 stop Charlotte Douglas
American Airlines Logo
4:56 pm - 11:09 amEYW  Key West-HHH Hilton Head Island
18h 13m2 stops Chicago O'Hare Intl Charlotte Douglas
$874American Airlines
Fri, Aug 21 - Tue, Aug 25
American Airlines Logo
11:40 am - 4:18 pmHHH  Hilton Head Island-EYW Key West
4h 38m1 stop Charlotte Douglas
American Airlines Logo
12:57 pm - 5:59 pmEYW  Key West-HHH Hilton Head Island
5h 02m1 stop Charlotte Douglas
$965American Airlines
Mon, Sep 7 - Sun, Sep 13
United Airlines Logo
1:50 pm - 1:29 pmHHH  Hilton Head Island-EYW Key West
23h 39m1 stop Newark
United Airlines Logo
2:20 pm - 12:59 pmEYW  Key West-HHH Hilton Head Island
22h 39m1 stop Newark
$987United Airlines
Thu, Sep 3 - Thu, Sep 10
American Airlines Logo
11:40 am - 4:18 pmHHH  Hilton Head Island-EYW Key West
4h 38m1 stop Charlotte Douglas
American Airlines Logo
7:47 pm - 4:45 pmEYW  Key West-HHH Hilton Head Island
20h 58m2 stops Miami Charlotte Douglas
$992American Airlines
Mon, Sep 7 - Sun, Sep 13
American Airlines Logo
11:04 am - 4:04 pmHHH  Hilton Head Island-EYW Key West
5h 00m1 stop Charlotte Douglas
American Airlines Logo
4:43 pm - 2:18 pmEYW  Key West-HHH Hilton Head Island
21h 35m2 stops Miami Charlotte Douglas
$1,013American Airlines
Mon, Nov 23 - Fri, Nov 27
American Airlines Logo
11:04 am - 6:47 pmHHH  Hilton Head Island-EYW Key West
7h 43m1 stop Charlotte Douglas
American Airlines Logo
1:17 pm - 10:36 amEYW  Key West-HHH Hilton Head Island
21h 19m1 stop Charlotte Douglas
$1,032American Airlines
Mon, Nov 23 - Fri, Nov 27

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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
Sep 3
HHH3:27 pmHilton Head Island
19h 29m
2 stops
EYW10:56 amKey West
Sep 10
EYW7:47 pmKey West
17h 58m
2 stops
HHH1:45 pmHilton Head Island
$811
American Airlines
Aug 21
HHH5:16 pmHilton Head Island
19h 49m
2 stops
EYW1:05 pmKey West
Aug 25
EYW1:40 pmKey West
21h 29m
2 stops
HHH11:09 amHilton Head Island
$853
American Airlines
Nov 23
HHH5:54 pmHilton Head Island
15h 54m
2 stops
EYW9:48 amKey West
Nov 27
EYW7:57 pmKey West
21h 10m
2 stops
HHH5:07 pmHilton Head Island
$864

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 August 10, 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 Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Thu 9/3

3:27 pm-10:56 am

2 stops19h 29m

Key West

Thu 9/10

7:47 pm-1:45 pm

2 stops17h 58m

$811

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Fri 8/21

5:16 pm-1:05 pm

2 stops19h 49m

Key West

Tue 8/25

1:40 pm-11:09 am

2 stops21h 29m

$853

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Mon 11/23

5:54 pm-9:48 am

2 stops15h 54m

Key West

Fri 11/27

7:57 pm-5:07 pm

2 stops21h 10m

$864

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Fri 8/21

11:40 am-4:18 pm

1 stop4h 38m

Key West

Tue 8/25

4:56 pm-1:17 pm

1 stop20h 21m

$869

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Fri 8/21

11:40 am-4:18 pm

1 stop4h 38m

Key West

Tue 8/25

4:56 pm-11:09 am

2 stops18h 13m

$874
Quickest round-trip

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Mon 9/7

11:40 am-4:18 pm

1 stop4h 38m

Key West

Sun 9/13

12:57 pm-5:59 pm

1 stop5h 02m

$965

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Thu 9/3

1:50 pm-1:29 pm

1 stop23h 39m

Key West

Thu 9/10

2:20 pm-12:59 pm

1 stop22h 39m

$987

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Mon 9/7

11:40 am-4:18 pm

1 stop4h 38m

Key West

Sun 9/13

7:47 pm-4:45 pm

2 stops20h 58m

$992

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Mon 11/23

11:04 am-4:04 pm

1 stop5h 00m

Key West

Fri 11/27

4:43 pm-2:18 pm

2 stops21h 35m

$1,013

Hilton Head IslandKey West

HHH Hilton Head Island - EYW Key West

HHHEYW

Hilton Head Island

Mon 11/23

11:04 am-6:47 pm

1 stop7h 43m

Key West

Fri 11/27

1:17 pm-10:36 am

1 stop21h 19m

$1,032

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 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 50% 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

4h 52m

Direct flights

None
The fastest flight from Hilton Head Island to Key West takes 4h 52m
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 4h 52m.

  • 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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