$200 Find Cheap Flights from Hilton Head Island to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilton Head Island to Florida Keys departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Florida Keys, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Florida Keys, as well as popular online travel agencies
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Cheap Flights from Hilton Head Island to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$282
Miami
Miami1 stop$282

Book Cheap Hilton Head Island to Florida Keys Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilton Head Island to Florida Keys that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hilton Head Island to Florida Keys

Tue, Sep 2 - Fri, Sep 5
American Airlines Logo
3:35 pm - 8:56 pmHHH-MIA
5h 21m1 stop
American Airlines Logo
7:05 am - 12:20 pmMIA-HHH
5h 15m1 stop
$282American Airlines
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Mon, Nov 17 - Mon, Nov 24
American Airlines Logo
6:50 pm - 11:47 pmHHH-MIA
4h 57m1 stop
American Airlines Logo
8:35 am - 2:19 pmMIA-HHH
5h 44m1 stop
$293American Airlines
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Fri, Nov 21 - Thu, Nov 27
American Airlines Logo
2:51 pm - 8:46 pmHHH-MIA
5h 55m1 stop
American Airlines Logo
5:43 am - 10:15 amMIA-HHH
4h 32m1 stop
$327American Airlines
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Sun, Aug 17 - Sun, Aug 24
American Airlines Logo
6:15 pm - 12:33 amHHH-MIA
6h 18m1 stop
American Airlines Logo
6:16 am - 11:30 amMIA-HHH
5h 14m1 stop
$347American Airlines
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Fri, Nov 21 - Tue, Nov 25
American Airlines Logo
2:51 pm - 8:46 pmHHH-MIA
5h 55m1 stop
American Airlines Logo
6:00 am - 10:17 amMIA-HHH
4h 17m1 stop
$367American Airlines
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Thu, Jan 22 - Sat, Jan 31
American Airlines Logo
6:14 pm - 6:59 amHHH-MIA
12h 45m2 stops
American Airlines Logo
8:00 am - 2:18 pmMIA-HHH
6h 18m1 stop
$395American Airlines
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Thu, Dec 25 - Tue, Dec 30
American Airlines Logo
6:26 pm - 11:23 pmHHH-MIA
4h 57m1 stop
American Airlines Logo
8:00 am - 2:16 pmMIA-HHH
6h 16m1 stop
$423American Airlines
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Tue, Aug 26 - Sat, Aug 30
Delta Logo
12:11 pm - 5:12 pmHHH-EYW
5h 01m1 stop
Delta Logo
6:20 pm - 3:22 pmEYW-HHH
21h 02m1 stop
$427Delta
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Fri, Nov 21 - Thu, Nov 27
American Airlines Logo
2:51 pm - 8:46 pmHHH-MIA
5h 55m1 stop
American Airlines Logo
7:30 pm - 10:15 amMIA-HHH
14h 45m2 stops
$445American Airlines
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Tue, Aug 26 - Sat, Aug 30
Delta Logo
12:11 pm - 5:12 pmHHH-EYW
5h 01m1 stop
Delta Logo
6:20 pm - 11:31 amEYW-HHH
17h 11m2 stops
$561Delta
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Booking Insights

KAYAK's insights & trends for Hilton Head Island to Florida Keys flights

Get data-powered insights and trends into flights from Hilton Head Island to Florida Keys to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Hilton Head Island to Florida Keys?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $488, prices are generally cheapest when you fly direct.

What’s the cheapest day of the week to fly from Hilton Head Island to Florida Keys?

The average price of all round-trip flights from Hilton Head Island to Florida Keys clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Hilton Head Island to Florida Keys, look for departures on Sundays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Florida Keys, Thursday is the cheapest day to fly and Tuesday is the most expensive.

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Good to know

Cheapest flight$200
Flight from Hilton Head Island to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Hilton Head Island to Florida Keys?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilton Head Island to Florida Keys.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Florida Keys?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Hilton Head Island to Florida Keys is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilton Head Island to Florida Keys?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Hilton Head Island to Florida Keys with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Florida Keys?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Hilton Head Island to Florida Keys up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Florida Keys?

    The cheapest time of day to fly to Florida Keys is generally in the morning, when round-trip flights cost $455 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $607.

Reviews of the top airline flying from Hilton Head Island to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Florida Keys. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilton Head Island to Florida Keys? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
6.9Entertainment
7.5Boarding
6.5Food
8.0Crew
7.2Comfort
Airline reviews

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

2.0 MediocreMatt, Jul 2025PHL - RSW
Read more American Airlines reviews

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Would have thought that they would gas up plane before everyone got on board

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Standard. No different than a discount carrier on a short trip.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

Hilton Head Island (HHH)

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