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Hilton Head Island

$139+ Cheap flights from Kissimmee, FL to Hilton Head Island (HHH)

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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheap flight deals from Kissimmee to Hilton Head Island

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

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$411
(American Airlines)

One-way from

$139
(Delta)
Provider with most accurate pricing for Orlando (ORL)-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Hilton Head Island flights.
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From Kissimmee to Hilton Head Island
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One-way flight from Kissimmee to Hilton Head Island
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Find flight deals from Kissimmee to Hilton Head Island

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

This American Airlines deal was found by Cheapflights users on 3/28. 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.
Sun 7/137:14 amMCO - HHH
1 stop4h 13mAmerican Airlines
Mon 7/142:45 pmHHH - MCO
1 stop6h 13mAmerican Airlines
Deal found 3/28$307

Cheapflights Fare Finder

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

Fly from

Kissimmee

Fly to

Hilton Head Island

Route

Depart

Return

Price

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sun 7/13

7:14 am-11:27 am

1 stop4h 13m

Hilton Head Island

Mon 7/14

2:45 pm-8:58 pm

1 stop6h 13m

$307

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 6/11

9:00 am-3:18 pm

1 stop6h 18m

$139

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sun 5/18

6:03 am-12:20 pm

1 stop6h 17m

$154

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 6/11

1:52 pm-11:04 am

3 stops21h 12m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Best time to book a flight from Kissimmee to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Kissimmee 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 Kissimmee to Hilton Head Island

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

Currently, January is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $275). Flying from Kissimmee to Hilton Head Island in March is currently the most expensive (average of $483). 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.

What is the cheapest time of day to fly from K1S to HHH?

Find hourly flight availability from Kissimmee to Hilton Head Island. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2025.

When flying from Kissimmee to Hilton Head Island, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Hilton Head Island ranges from 2.4 - 7.8 inches per month. August is typically the wettest month, when rainfall can reach 7.8 in. November is typically the driest time to visit Hilton Head Island when rainfall is around 2.4 in.

Temperature in Hilton Head Island by month

Plan your trip to Hilton Head Island by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Hilton Head Island, 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 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 50.0 F).

Reviews of airlines servicing Hilton Head Island

Get insights into the airlines that provide service to Hilton Head Island. 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 Hilton Head Island. Reviews last updated March 28, 2025.
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,896 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,603 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,896 reviews

Entertainment

7.9

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Hilton Head Island. 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 into for flights to Hilton Head Island from Kissimmee?

    Hilton Head Island (HHH) is the airport you will fly into if you book a flight from Kissimmee to Hilton Head Island. You should not have trouble finding flights to Hilton Head from Kissimmee; the airport handles an average of 0 inbound flights from Kissimmee per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Hilton Head Island airport from Kissimmee. It is only a 3.3 mi journey from Hilton Head (HHH) to Hilton Head Island’s city center.

  • What are the cheapest airlines to fly from Kissimmee to Hilton Head Island one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $139. American Airlines flights start at $154 while deals on United Airlines start at $353 one-way.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kissimmee to Hilton Head Island.

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

    Yes. Cheapflights offers flight deals from Kissimmee to Hilton Head Island 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 Kissimmee to Hilton Head Island?

    Currently, January is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $275). Flying from Kissimmee to Hilton Head Island in March is currently the most expensive (average of $483). 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

Traveling to a place near Kissimmee?

Book flights to Kissimmee if you plan to visit one of these locations
Beaufort
Bluffton

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Top airline flying from Kissimmee to Hilton Head Island

Discover the top airline that operate flights from Kissimmee to Hilton Head Island. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$222Average$355FlexibilityNo cancel feeOn-time71%
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