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Florida Keys

$119+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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 12/206:13 pmHHH - MIA
1 stop4h 35mAmerican Airlines
Mon 12/226:00 amMIA - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/10$338
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/127:08 pmHHH - MIA
1 stop4h 44mAmerican Airlines
Mon 12/155:45 amMIA - HHH
1 stop6h 37mAmerican Airlines
Deal found 12/10$429
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/123:27 pmHHH - MIA
1 stop6h 51mAmerican Airlines
Sun 12/146:00 amMIA - HHH
1 stop5h 51mAmerican Airlines
Deal found 12/10$444
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/136:48 pmHHH - MIA
1 stop6h 04mAmerican Airlines
Mon 12/155:45 amMIA - HHH
1 stop6h 37mAmerican Airlines
Deal found 12/10$474
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/136:48 pmHHH - MIA
1 stop6h 04mAmerican Airlines
Sun 12/146:00 amMIA - HHH
1 stop5h 51mAmerican Airlines
Deal found 12/10$489
This American Airlines deal was found by Cheapflights users on 12/11. 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 28mAmerican Airlines
Mon 12/296:00 amMIA - HHH
1 stop4h 44mAmerican Airlines
Deal found 12/11$633
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/2511:14 amHHH - EYW
2 stops23h 52mAmerican Airlines
Mon 12/2912:55 pmEYW - HHH
1 stop4h 48mAmerican Airlines
Deal found 12/10$1,131

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$263
(American Airlines)

One-way from

$119
(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 December 12, 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

Wed 2/18

3:35 pm-10:43 pm

1 stop7h 08m

Miami

Mon 2/23

9:25 am-2:27 pm

1 stop5h 02m

$263

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 12/25

2:46 pm-7:14 am

2 stops16h 28m

Miami

Mon 12/29

6:00 am-10:44 am

1 stop4h 44m

$633

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 3/31

3:31 pm-10:18 pm

1 stop6h 47m

Key West

Fri 4/3

12:55 pm-5:46 pm

1 stop4h 51m

$643

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Thu 12/25

11:14 am-11:06 am

2 stops23h 52m

Key West

Mon 12/29

12:55 pm-5:43 pm

1 stop4h 48m

$1,131

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Tue 1/6

12:51 pm-5:41 pm

1 stop4h 50m

$119

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Wed 3/11

2:58 pm-9:28 pm

1 stop6h 30m

$149

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Tue 3/10

12:23 pm-7:43 pm

1 stop7h 20m

$149

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 3/12

6:20 pm-11:43 pm

1 stop5h 23m

$149

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Fri 3/13

6:20 pm-11:43 pm

1 stop5h 23m

$228

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 5/1

12:00 pm-5:12 pm

1 stop5h 12m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 12 results
1
2

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 December 12, 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
11,050 reviews

Entertainment

6.9

Food

6.5

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

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
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Entertainment

6.9

Food

6.5

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

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 $263, American Airlines can have you in Florida Keys from Hilton Head Island in 7h 08m. 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

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