HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$308+ Cheap flights from Hilton Head Island to Key West (HHH - EYW)

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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Aug 8 — Aug 151
Sat 8/8
Sat 8/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hilton Head Island to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Hilton Head Island to Key West

Cheapest flights from Hilton Head Island to Key West
Explore the most affordable flight options available from Hilton Head Island to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 9, 2026.

This American Airlines deal was found by Cheapflights users on 7/6. 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.
Mon 8/3111:40 am
HHH
-
EYW
1 stop4h 38m
American Airlines
Fri 9/44:56 pm
EYW
-
HHH
1 stop19h 19m
American Airlines
Deal found 7/6$676
This American Airlines deal was found by Cheapflights users on 7/6. 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.
Tue 7/214:55 pm
HHH
-
EYW
2 stops20h 19m
American Airlines
Sat 7/257:55 pm
EYW
-
HHH
2 stops18h 21m
American Airlines
Deal found 7/6$851
This American Airlines deal was found by Cheapflights users on 7/5. 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.
Mon 7/2011:47 am
HHH
-
EYW
1 stop4h 24m
American Airlines
Fri 7/244:21 pm
EYW
-
HHH
1 stop21h 00m
American Airlines
Deal found 7/5$918
This American Airlines deal was found by Cheapflights users on 7/4. 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 7/1712:50 pm
HHH
-
EYW
1 stop5h 58m
American Airlines
Sun 7/197:40 pm
EYW
-
HHH
2 stops18h 36m
American Airlines
Deal found 7/4$923
This United Airlines deal was found by Cheapflights users on 7/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/203:05 pm
HHH
-
EYW
2 stops22h 25m
United Airlines
Fri 7/242:26 pm
EYW
-
HHH
2 stops47h 55m
United Airlines
Deal found 7/5$1,122

Find flight deals from Hilton Head Island to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Key West (EYW). 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 July 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$676
(American Airlines)

One-way from

$308
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Key West flights.
Search Deals
From Hilton Head Island to Key West
Search Deals
One-way flight from Hilton Head Island to Key West
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated July 9, 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

Mon 8/31

11:40 am-4:18 pm

1 stop4h 38m

Key West

Fri 9/4

4:56 pm-12:15 pm

1 stop19h 19m

$676

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 7/21

4:55 pm-1:14 pm

2 stops20h 19m

Key West

Sat 7/25

7:55 pm-2:16 pm

2 stops18h 21m

$851

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 7/20

11:47 am-4:11 pm

1 stop4h 24m

Key West

Fri 7/24

4:21 pm-1:21 pm

1 stop21h 00m

$918

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 7/20

3:05 pm-1:30 pm

2 stops22h 25m

Key West

Fri 7/24

2:26 pm-2:21 pm

2 stops47h 55m

$1,122
Cheapest one-way
Quickest one-way

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 8/31

11:40 am-4:18 pm

1 stop4h 38m

$308

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 9/1

12:15 pm-5:20 pm

1 stop5h 05m

$308

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Thu 9/3

11:40 am-4:18 pm

1 stop4h 38m

$308

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 8/28

4:18 pm-12:26 pm

2 stops20h 08m

$335

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Sun 8/30

1:52 pm-12:55 pm

2 stops23h 03m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/6

Sorted by cheapest first

Compare providers for flights from Hilton Head Island to Key West

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 Hilton Head Island to Key West in July.
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 Hilton Head Island-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hilton Head Island-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Hilton Head Island-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hilton Head Island-Key West 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 Hilton Head Island-Key West 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 Hilton Head Island to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Hilton Head Island 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.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Key West. 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 Hilton Head Island to Key West?

    For as low as $676, American Airlines can have you in Key West from Hilton Head Island in 4h 38m. Airlines will cover a distance of 533 mi.

  • Can I find deals for flights from Hilton Head Island to Key West that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Key West.

  • Can I find deals for business class flights from Hilton Head Island to Key West?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hilton Head Island to Key West

See prices for flight routes from nearby airports that may be better suited for you.
Charlotte to Fort Lauderdale flights
Charlotte to Miami flights
Charlotte to Orlando flights
Charlotte to Tampa flights
Charleston to Miami flights
Charlotte to West Palm Beach flights
Charleston to Fort Lauderdale flights
Myrtle Beach to Fort Lauderdale flights
Charleston to Orlando flights
Greenville to Miami flights
Columbia to Miami flights
Charlotte to Jacksonville flights
Charlotte to Key West flights
Charlotte to Panama City flights
Columbia to Orlando flights
Greenville to Fort Lauderdale flights
Charlotte to Pensacola flights
Charlotte to Fort Myers flights
Charleston to Tampa flights
Savannah to Miami flights
Columbia to Fort Lauderdale flights
Myrtle Beach to Orlando flights
Greenville to Fort Myers flights
Charlotte to Sarasota flights
Greenville to Orlando Sanford Intl flights
Columbia to Tampa flights
Greenville to Orlando flights
Myrtle Beach to Miami flights
Greenville to Pensacola flights
Greenville to Jacksonville flights
Greenville to Tampa flights
Columbia to Pensacola flights
Greenville to West Palm Beach flights
Charlotte to Gainesville flights
Greenville to Panama City flights
Myrtle Beach to Tampa flights
Myrtle Beach to Key West flights
Charlotte to Daytona Beach flights
Charleston to Pensacola flights
Savannah to Orlando flights
Charleston to Key West flights
Myrtle Beach to Sarasota flights
Savannah to Tampa flights
Greenville to Sarasota flights
Columbia to Fort Myers flights
Charlotte to Melbourne flights
Savannah to Fort Lauderdale flights
Columbia to Sarasota flights
Columbia to Key West flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.