$110 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 1/1. 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, 0 bags

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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Flight Deals

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

Sat, Jan 24 - Sun, Jan 25
American Airlines Logo
3:29 pm - 10:22 pm
HHH
-
MIA
6h 53m1 stop
American Airlines Logo
7:07 am - 12:20 pm
MIA
-
HHH
5h 13m1 stop
$219American Airlines
Sat, Jan 17 - Fri, Jan 23
American Airlines Logo
3:29 pm - 9:47 pm
HHH
-
EYW
6h 18m1 stop
American Airlines Logo
7:08 am - 12:20 pm
EYW
-
HHH
5h 12m1 stop
$353American Airlines
Sat, Jan 17 - Thu, Jan 22
American Airlines Logo
3:29 pm - 9:47 pm
HHH
-
EYW
6h 18m1 stop
American Airlines Logo
6:06 am - 2:59 pm
EYW
-
HHH
8h 53m2 stops
$358American Airlines
Sat, Jan 24 - Sun, Jan 25
American Airlines Logo
3:29 pm - 9:10 pm
HHH
-
MIA
5h 41m1 stop
American Airlines Logo
10:45 pm - 12:20 pm
MIA
-
HHH
13h 35m2 stops
$362American Airlines
Sat, Jan 17 - Thu, Jan 22
American Airlines Logo
3:29 pm - 11:56 pm
HHH
-
EYW
8h 27m2 stops
American Airlines Logo
6:06 am - 2:59 pm
EYW
-
HHH
8h 53m2 stops
$363American Airlines
Fri, Jan 16 - Thu, Jan 22
American Airlines Logo
3:29 pm - 9:47 pm
HHH
-
EYW
6h 18m1 stop
American Airlines Logo
7:08 am - 12:20 pm
EYW
-
HHH
5h 12m1 stop
$387American Airlines
Fri, Jan 16 - Thu, Jan 22
American Airlines Logo
3:29 pm - 9:47 pm
HHH
-
EYW
6h 18m1 stop
American Airlines Logo
6:06 am - 2:59 pm
EYW
-
HHH
8h 53m2 stops
$392American Airlines
Tue, Mar 10 - Thu, Mar 12
American Airlines Logo
12:23 pm - 4:50 pm
HHH
-
MIA
4h 27m1 stop
American Airlines Logo
7:00 am - 2:22 pm
MIA
-
HHH
7h 22m1 stop
$397American Airlines
Thu, Jan 29 - Thu, Feb 5
American Airlines Logo
3:29 pm - 11:56 pm
HHH
-
EYW
8h 27m2 stops
American Airlines Logo
6:06 am - 2:59 pm
EYW
-
HHH
8h 53m2 stops
$397American Airlines
Thu, Mar 12 - Sun, Mar 15
American Airlines Logo
6:20 pm - 11:43 pm
HHH
-
MIA
5h 23m1 stop
American Airlines Logo
9:30 am - 2:22 pm
MIA
-
HHH
4h 52m1 stop
$447American Airlines
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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $529 on average.

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.

Find deals

Good to know

Cheapest flight$110
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 11049 reviews
7.5Boarding
7.2Comfort
6.5Food
6.9Entertainment
8.0Crew
Airline reviews

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

10.0 ExcellentJamie, Dec 2025
DCA - TPA
Read more American Airlines reviews

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

Very good but wish they had the seat-back video screens for movies & games

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports

Hilton Head Island (HHH)