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$307+ Cheap flights from Hilton Head Island (HHH) to Florida Keys

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — EYW
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
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 March 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$307
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Miami flight deals.
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Provider most trusted by Cheapflights users for Hilton Head Island-Miami flights.
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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 March 3, 2025.

This American Airlines deal was found by Cheapflights users on 3/2. 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 4/172:50 pmHHH - MIA
1 stop5h 57mAmerican Airlines
Sun 4/208:22 amMIA - HHH
1 stop5h 58mAmerican Airlines
Deal found 3/2$307
This American Airlines deal was found by Cheapflights users on 3/2. 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 10/312:37 pmHHH - EYW
1 stop4h 11mAmerican Airlines
Tue 10/71:25 pmEYW - HHH
1 stop4h 11mAmerican Airlines
Deal found 3/2$472
This United Airlines deal was found by Cheapflights users on 3/2. 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.
Sat 5/35:00 pmHHH - MIA
2 stops18h 29mUnited Airlines
Sat 5/107:53 amMIA - HHH
2 stops31h 36mUnited Airlines
Deal found 3/2$747

Find flights from Hilton Head Island to Florida Keys within your budget

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 March 3, 2025.

Fly from

Hilton Head Island

Fly to

Florida Keys

Route

Depart

Return

Price

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Thu 4/17

2:50 pm-8:47 pm

1 stop5h 57m

Miami

Sun 4/20

8:22 am-2:20 pm

1 stop5h 58m

$307

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Sat 5/3

5:00 pm-11:29 am

2 stops18h 29m

Miami

Sat 5/10

7:53 am-3:29 pm

2 stops31h 36m

$747

Hilton Head IslandKey West

HHH - EYW

HHHEYW

Hilton Head Island

Mon 3/17

5:59 pm-11:13 am

2 stops17h 14m

Key West

Fri 3/21

6:20 pm-11:04 am

1 stop16h 44m

$907

Hilton Head IslandMiami

HHH - MIA

HHHMIA

Hilton Head Island

Sun 3/30

4:18 pm-11:51 pm

1 stop7h 33m

$1,512

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

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.

Travel insights for flights from Hilton Head Island to Florida Keys

Get recent, data-driven insights about flights from Hilton Head Island to Florida Keys including ideal travel times, pricing trends, and more.

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 $503). 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.

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

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 March 3, 2025.
United Airlines
7.4
Good
8,679 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

United Airlines
7.4
Good
8,679 reviews
United Airlines
7.4
Good
8,679 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,679 reviews

Food

6.6

Crew

8.1

Comfort

7.3

Overall

7.4

Entertainment

7.1

Boarding

7.7

Reviews

1 / 20

2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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 $503). 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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