$675+ Cheap flights from Hilton Head Island to Key West (HHH - EYW)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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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
Best
Last-minute
Cheapest flights from Hilton Head Island to Key WestExplore 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 October 30, 2026.
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 October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/2611:06 am -
2 stops26h 54m
Thu 12/35:16 pm -
2 stops17h 16m
Deal found 10/27![American Airlines logo]()
$730
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/1012:25 pm -
1 stop5h 36m
Sat 11/145:12 pm -
2 stops17h 22m
Deal found 10/26![American Airlines logo]()
$985
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/1211:04 am -
1 stop7h 43m
Mon 11/167:57 pm -
2 stops19h 47m
Deal found 10/28![American Airlines logo]()
$1,176
Best flights from Hilton Head Island to Key WestDiscover carefully curated flight deals from Hilton Head Island to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
Discover carefully curated flight deals from Hilton Head Island to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 30, 2026.
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sun 1/2412:37 pm -
1 stop5h 17m
Sun 1/319:58 am -
2 stops5h 55m
Deal found 10/29![American Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 4/273:05 pm -
1 stop24h 01m
Sat 5/14:05 pm -
2 stops19h 07m
Deal found 10/29![United Airlines logo]()
$912
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/2611:06 am -
2 stops26h 54m
Thu 12/35:16 pm -
2 stops17h 16m
Deal found 10/27![American Airlines logo]()
$730
Last-minute flights from Hilton Head Island to Key WestDiscover last-minute flight deals from Hilton Head Island to Key West. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Hilton Head Island to Key West. Data last updated October 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/1012:25 pm -
1 stop5h 36m
Sat 11/145:12 pm -
2 stops17h 22m
Deal found 10/26![American Airlines logo]()
$985
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/1211:04 am -
1 stop7h 43m
Mon 11/167:57 pm -
2 stops19h 47m
Deal found 10/28![American Airlines logo]()
$1,176
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 11/2611:06 am -
2 stops26h 54m
Thu 12/35:16 pm -
2 stops17h 16m
Deal found 10/27![American Airlines logo]()
$730
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $675 (American Airlines) |
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 7,457,451 searches. Data last updated October 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
Cheapest round-trip
Quickest round-trip
Hilton Head IslandKey West
HHH Hilton Head Island - EYW Key West
HHHEYW
Hilton Head Island
Sun 1/24
12:37 pm-5:54 pm
1 stop5h 17m
Key West
Sun 1/31
9:58 am-3:53 pm
2 stops5h 55m
$675
Hilton Head IslandKey West
HHH Hilton Head Island - EYW Key West
HHHEYW
Hilton Head Island
Thu 11/26
11:06 am-2:00 pm
2 stops26h 54m
Key West
Thu 12/3
5:16 pm-10:32 am
2 stops17h 16m
$730
Hilton Head IslandKey West
HHH Hilton Head Island - EYW Key West
HHHEYW
Hilton Head Island
Tue 4/27
3:05 pm-3:06 pm
1 stop24h 01m
Key West
Sat 5/1
4:05 pm-11:12 am
2 stops19h 07m
$912
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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.
HHH-EYW
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.
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