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$124+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
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 February 22, 2026.

This American Airlines deal was found by Cheapflights users on 2/20. 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 5/285:21 pm
HHH
-
MIA
1 stop7h 26m
American Airlines
Fri 5/297:40 am
MIA
-
HHH
1 stop6h 38m
American Airlines
Deal found 2/20$247
This American Airlines deal was found by Cheapflights users on 2/18. 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 2/255:19 pm
HHH
-
MIA
1 stop5h 26m
American Airlines
Wed 3/47:10 am
MIA
-
HHH
1 stop4h 43m
American Airlines
Deal found 2/18$287
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/1311:03 am
HHH
-
MIA
1 stop5h 52m
American Airlines
Sat 5/167:45 am
MIA
-
HHH
1 stop6h 39m
American Airlines
Deal found 2/18$313
This American Airlines deal was found by Cheapflights users on 2/22. 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 11/262:51 pm
HHH
-
MIA
1 stop5h 55m
American Airlines
Fri 12/46:00 am
MIA
-
HHH
1 stop5h 51m
American Airlines
Deal found 2/22$317
This American Airlines deal was found by Cheapflights users on 2/19. 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 2/236:20 pm
HHH
-
MIA
1 stop5h 23m
American Airlines
Wed 2/259:25 am
MIA
-
HHH
1 stop7h 19m
American Airlines
Deal found 2/19$399
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/232:58 pm
HHH
-
MIA
1 stop5h 49m
American Airlines
Sun 4/266:54 am
MIA
-
HHH
1 stop7h 32m
American Airlines
Deal found 2/19$407
This American Airlines deal was found by Cheapflights users on 2/18. 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 3/56:20 pm
HHH
-
MIA
1 stop5h 23m
American Airlines
Mon 3/99:30 am
MIA
-
HHH
1 stop4h 52m
American Airlines
Deal found 2/18$422
This American Airlines deal was found by Cheapflights users on 2/20. 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 3/74:31 pm
HHH
-
MIA
1 stop14h 26m
American Airlines
Wed 3/1111:07 am
MIA
-
HHH
1 stop6h 37m
American Airlines
Deal found 2/20$437
This American Airlines deal was found by Cheapflights users on 2/19. 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 3/56:20 pm
HHH
-
MIA
1 stop5h 23m
American Airlines
Thu 3/1211:07 am
MIA
-
HHH
1 stop6h 37m
American Airlines
Deal found 2/19$487
This American Airlines deal was found by Cheapflights users on 2/20. 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 5/235:18 pm
HHH
-
MIA
1 stop7h 29m
American Airlines
Sat 5/306:20 am
MIA
-
HHH
1 stop4h 50m
American Airlines
Deal found 2/20$532
This American Airlines deal was found by Cheapflights users on 2/21. 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 4/16:15 pm
HHH
-
EYW
1 stop4h 22m
American Airlines
Sat 4/47:42 pm
EYW
-
HHH
2 stops18h 40m
American Airlines
Deal found 2/21$754
This American Airlines deal was found by Cheapflights users on 2/20. 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 6/1011:40 am
HHH
-
EYW
1 stop7h 09m
American Airlines
Sat 6/207:49 pm
EYW
-
HHH
2 stops16h 37m
American Airlines
Deal found 2/20$800

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 February 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$247
(American Airlines)

One-way from

$124
(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 February 22, 2026.
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 5/13

11:03 am-4:55 pm

1 stop5h 52m

Miami

Sat 5/16

7:45 am-2:24 pm

1 stop6h 39m

$313

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 3/5

6:20 pm-11:43 pm

1 stop5h 23m

Miami

Mon 3/9

9:30 am-2:22 pm

1 stop4h 52m

$422

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 3/5

6:20 pm-11:43 pm

1 stop5h 23m

Miami

Thu 3/12

9:30 am-2:22 pm

1 stop4h 52m

$487

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Fri 3/13

2:58 pm-9:45 pm

1 stop6h 47m

Miami

Mon 3/16

9:30 am-2:22 pm

1 stop4h 52m

$517

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Sat 8/8

6:15 pm-11:17 pm

1 stop5h 02m

Miami

Sun 8/16

5:00 am-11:30 am

1 stop6h 30m

$537

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Mon 3/23

2:58 pm-9:45 pm

1 stop6h 47m

Miami

Sat 4/4

7:50 am-2:22 pm

1 stop6h 32m

$598

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 4/23

5:04 pm-10:51 pm

1 stop5h 47m

Miami

Sun 4/26

8:54 am-4:34 pm

2 stops7h 40m

$644

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 4/23

4:11 pm-10:45 pm

3 stops30h 34m

Miami

Sun 4/26

6:05 am-2:16 pm

2 stops32h 11m

$661

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Wed 6/10

11:40 am-6:49 pm

1 stop7h 09m

Key West

Sat 6/20

7:49 pm-12:26 pm

2 stops16h 37m

$800

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Wed 4/1

11:03 am-7:12 pm

2 stops8h 09m

Key West

Sat 4/4

7:42 pm-2:22 pm

2 stops18h 40m

$824

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 26 results
1
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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, January is the cheapest month in which you can book a flight from Hilton Head Island to Florida Keys (average of $78). Flying from Hilton Head Island to Florida Keys in April is currently the most expensive (average of $431). 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 February 22, 2026.
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
11,338 reviews

Food

6.4

Overall

7.2

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,338 reviews
American Airlines
7.2
Good
11,338 reviews

Food

6.4

Overall

7.2

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 $313, American Airlines can have you in Florida Keys from Hilton Head Island in 5h 52m. The distance from Hilton Head Island to Florida Keys is about 444 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Florida Keys (average of $78). Flying from Hilton Head Island to Florida Keys in April is currently the most expensive (average of $431). 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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