HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Florida Keys

$149+ Cheap flights from Hilton Head Island (HHH) to Florida Keys

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hilton Head Island to Florida Keys 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.

Find flight deals from Hilton Head Island to Florida Keys

Cheapest flights from Hilton Head Island to Florida Keys
Explore the most affordable flight options available from Hilton Head Island to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/25. 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 11/103:27 pmHHH - MIA
1 stop5h 30mAmerican Airlines
Fri 11/141:30 pmMIA - HHH
1 stop5h 07mAmerican Airlines
Deal found 10/25$247
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.
Thu 10/3012:45 pmHHH - MIA
1 stop5h 06mAmerican Airlines
Sun 11/25:00 amMIA - HHH
1 stop5h 49mAmerican Airlines
Deal found 10/26$351
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 12/252:46 pmHHH - MIA
2 stops16h 18mAmerican Airlines
Mon 12/296:00 amMIA - HHH
1 stop4h 44mAmerican Airlines
Deal found 10/27$485
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 12/306:13 pmHHH - EYW
1 stop4h 45mAmerican Airlines
Thu 1/18:00 amEYW - HHH
1 stop6h 16mAmerican Airlines
Deal found 10/26$498
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.
Wed 12/3111:14 amHHH - EYW
2 stops5h 55mAmerican Airlines
Thu 1/18:00 amEYW - HHH
1 stop6h 16mAmerican Airlines
Deal found 10/26$503
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.
Mon 12/296:13 pmHHH - EYW
1 stop4h 31mAmerican Airlines
Thu 1/18:00 amEYW - HHH
1 stop6h 16mAmerican Airlines
Deal found 10/26$508
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.
Fri 12/266:13 pmHHH - MIA
1 stop6h 34mAmerican Airlines
Tue 12/306:00 amMIA - HHH
1 stop4h 44mAmerican Airlines
Deal found 10/27$538
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 12/306:13 pmHHH - EYW
1 stop4h 45mAmerican Airlines
Wed 12/318:09 pmEYW - HHH
2 stops14h 35mAmerican Airlines
Deal found 10/26$541
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.
Sat 12/276:13 pmHHH - MIA
2 stops14h 28mAmerican Airlines
Tue 12/306:00 amMIA - HHH
1 stop4h 44mAmerican Airlines
Deal found 10/26$550
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.
Mon 12/296:13 pmHHH - EYW
1 stop4h 31mAmerican Airlines
Wed 12/318:09 pmEYW - HHH
2 stops18h 07mAmerican Airlines
Deal found 10/26$551
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.
Tue 11/111:02 pmHHH - MIA
2 stops8h 28mAmerican Airlines
Sat 11/157:01 amMIA - HHH
1 stop4h 15mAmerican Airlines
Deal found 10/27$609
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.
Fri 12/266:13 pmHHH - MIA
1 stop6h 34mAmerican Airlines
Mon 12/296:00 amMIA - HHH
1 stop4h 44mAmerican Airlines
Deal found 10/26$626

Cheap flight deals from Hilton Head Island to Florida Keys

Keep the following information in mind while searching for Hilton Head Island to Florida Keys flight deals. Data was last updated October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$247
(American Airlines)

One-way from

$149
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Miami flights.
Search Deals
From Hilton Head Island to Florida Keys
Search Deals
One-way flight from Hilton Head Island to Florida Keys
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Florida Keys 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 October 28, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Florida Keys that are best for you.

Fly from

Hilton Head Island

Fly to

Florida Keys

Route

Depart

Return

Price

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Mon 11/10

3:27 pm-8:57 pm

1 stop5h 30m

Miami

Fri 11/14

1:30 pm-6:37 pm

1 stop5h 07m

$247

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Tue 11/11

7:07 pm-11:49 pm

1 stop4h 42m

Miami

Sat 11/15

8:35 am-2:19 pm

1 stop5h 44m

$247

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Wed 3/11

4:10 pm-11:59 pm

2 stops7h 49m

Key West

Wed 3/18

8:10 am-2:19 pm

1 stop6h 09m

$372

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 12/25

2:46 pm-7:04 am

2 stops16h 18m

Miami

Mon 12/29

6:00 am-10:44 am

1 stop4h 44m

$485

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Wed 12/31

6:13 pm-10:44 pm

1 stop4h 31m

Key West

Thu 1/1

8:00 am-2:16 pm

1 stop6h 16m

$498

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 12/30

6:13 pm-10:58 pm

1 stop4h 45m

Key West

Thu 1/1

8:00 am-2:16 pm

1 stop6h 16m

$498

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 12/29

6:13 pm-10:44 pm

1 stop4h 31m

Key West

Thu 1/1

8:00 am-2:16 pm

1 stop6h 16m

$508

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Fri 12/26

6:13 pm-12:47 am

1 stop6h 34m

Miami

Tue 12/30

6:00 am-10:44 am

1 stop4h 44m

$538

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Sat 12/27

6:13 pm-10:48 pm

1 stop4h 35m

Miami

Tue 12/30

6:00 am-10:44 am

1 stop4h 44m

$538

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Wed 12/31

11:14 am-3:57 pm

1 stop4h 43m

Key West

Wed 12/31

8:09 pm-10:44 am

2 stops14h 35m

$541

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 23 results
1
2
3

Best time to book a flight from Hilton Head Island to Florida Keys

Have a flexible travel schedule? Discover the best time to fly to Florida Keys 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.

Cheapflights Insights

Everything you need to know about your flight from Hilton Head Island to Florida Keys

What is the cheapest month to book a flight from Hilton Head Island to Florida Keys?

Currently, February is the cheapest month in which you can book a flight from Hilton Head Island to Florida Keys (average of $64). Flying from Hilton Head Island to Florida Keys in April is currently the most expensive (average of $454). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Florida Keys. Reviews last updated October 28, 2025.
Read reviews from past customers who have flown American Airlines from Hilton Head Island to Florida Keys. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break
American Airlines
7.2
Good
11,032 reviews
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Florida Keys. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hilton Head Island to Florida Keys?

    Located just 3.3 mi from the city center, Hilton Head Island (HHH) is the airport most travelers will use when flying to Florida Keys from Hilton Head Island.

  • How long is the flight from Hilton Head Island to Florida Keys?

    For as low as $247, American Airlines can have you in Florida Keys from Hilton Head Island in 5h 30m. The distance from Hilton Head Island to Florida Keys is about 444 mi.

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

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

  • How can I find direct flights from Hilton Head Island to Florida Keys?

    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 Florida Keys.

  • Can I find deals for business class flights from Hilton Head Island to Florida Keys?

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

  • What is the cheapest month to book a flight from Hilton Head Island to Florida Keys?

    Currently, February is the cheapest month in which you can book a flight from Hilton Head Island to Florida Keys (average of $64). Flying from Hilton Head Island to Florida Keys in April is currently the most expensive (average of $454). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 Florida Keys

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