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Florida Keys

$118+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
1 adult, Economy
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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 August 16, 2025.

Round-trip from

$317
(American Airlines)

One-way from

$118
(Delta)
From Hilton Head Island to Florida Keys
Search Deals
One-way flight from Hilton Head Island to Florida Keys
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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 August 16, 2025.

This American Airlines deal was found by Cheapflights users on 8/13. 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 9/205:19 pmHHH - MIA
1 stop6h 29mAmerican Airlines
Tue 9/237:05 amMIA - HHH
1 stop5h 12mAmerican Airlines
Deal found 8/13$317
This American Airlines deal was found by Cheapflights users on 8/14. 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 9/273:26 pmHHH - MIA
1 stop6h 03mAmerican Airlines
Sat 10/45:18 amMIA - HHH
1 stop7h 02mAmerican Airlines
Deal found 8/14$347
This American Airlines deal was found by Cheapflights users on 8/13. 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 8/296:15 pmHHH - MIA
1 stop4h 57mAmerican Airlines
Tue 9/26:16 amMIA - HHH
1 stop5h 43mAmerican Airlines
Deal found 8/13$367
This American Airlines deal was found by Cheapflights users on 8/15. 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 9/125:20 pmHHH - MIA
1 stop6h 36mAmerican Airlines
Fri 9/198:20 amMIA - HHH
1 stop6h 36mAmerican Airlines
Deal found 8/15$447
This American Airlines deal was found by Cheapflights users on 8/15. 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 12/252:26 pmHHH - MIA
1 stop7h 03mAmerican Airlines
Mon 12/298:00 amMIA - HHH
1 stop4h 21mAmerican Airlines
Deal found 8/15$483
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/153:35 pmHHH - MIA
1 stop6h 32mAmerican Airlines
Fri 8/226:16 amMIA - HHH
1 stop5h 43mAmerican Airlines
Deal found 8/14$487
This American Airlines deal was found by Cheapflights users on 8/14. 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 10/35:20 pmHHH - EYW
2 stops17h 34mAmerican Airlines
Tue 10/77:52 pmEYW - HHH
2 stops20h 59mAmerican Airlines
Deal found 8/14$626
This American Airlines deal was found by Cheapflights users on 8/12. 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 8/1312:29 pmHHH - MIA
1 stop4h 23mAmerican Airlines
Fri 8/1511:50 amMIA - HHH
1 stop5h 05mAmerican Airlines
Deal found 8/12$667
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Fri 9/1212:06 pmHHH - MIA
1 stop7h 05mUnited Airlines
Fri 9/193:35 pmMIA - HHH
2 stops19h 50mUnited Airlines
Deal found 8/15$687
This American Airlines deal was found by Cheapflights users on 8/15. 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 8/2612:29 pmHHH - EYW
1 stop4h 17mAmerican Airlines
Sat 8/3011:26 amEYW - HHH
2 stops24h 04mAmerican Airlines
Deal found 8/15$692
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2612:11 pmHHH - EYW
1 stop5h 01mDelta
Sat 8/302:00 pmEYW - HHH
1 stop25h 22mDelta
Deal found 8/13$697
This American Airlines deal was found by Cheapflights users on 8/14. 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 8/296:15 pmHHH - EYW
2 stops18h 54mAmerican Airlines
Tue 9/21:29 pmEYW - HHH
2 stops22h 48mAmerican Airlines
Deal found 8/14$866

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 August 16, 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

Sat 9/20

5:19 pm-11:48 pm

1 stop6h 29m

Miami

Tue 9/23

7:05 am-12:17 pm

1 stop5h 12m

$317

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Sat 9/27

3:26 pm-9:29 pm

1 stop6h 03m

Miami

Sat 10/4

5:18 am-12:20 pm

1 stop7h 02m

$347

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Fri 8/29

6:15 pm-11:12 pm

1 stop4h 57m

Miami

Tue 9/2

6:16 am-11:59 am

1 stop5h 43m

$367

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Fri 9/12

5:20 pm-11:56 pm

1 stop6h 36m

Miami

Fri 9/19

8:20 am-2:56 pm

1 stop6h 36m

$447

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 12/25

12:41 pm-7:00 pm

1 stop6h 19m

Miami

Mon 12/29

8:00 am-12:21 pm

1 stop4h 21m

$483

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Fri 10/3

5:20 pm-10:54 am

2 stops17h 34m

Key West

Tue 10/7

7:52 pm-4:51 pm

2 stops20h 59m

$626

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Fri 9/12

12:06 pm-7:11 pm

1 stop7h 05m

Miami

Fri 9/19

3:35 pm-11:25 am

2 stops19h 50m

$687

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 8/26

12:29 pm-4:46 pm

1 stop4h 17m

Key West

Sat 8/30

11:26 am-11:30 am

2 stops24h 04m

$692

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Tue 8/26

12:11 pm-5:12 pm

1 stop5h 01m

Key West

Sat 8/30

2:00 pm-3:22 pm

1 stop25h 22m

$697

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Tue 10/7

12:17 pm-5:09 pm

1 stop4h 52m

$118

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 22 results
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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, August is the cheapest month in which you can book a flight from Hilton Head Island to Florida Keys (average of $328). Flying from Hilton Head Island to Florida Keys in March is currently the most expensive (average of $492). 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 August 16, 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
10,000 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.5

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Food

6.5

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.

  • 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, August is the cheapest month in which you can book a flight from Hilton Head Island to Florida Keys (average of $328). Flying from Hilton Head Island to Florida Keys in March is currently the most expensive (average of $492). 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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