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Kissimmee

$173+ Cheap flights from Hilton Head Island (HHH) to Kissimmee, FL

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MCO
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Hilton Head Island to Kissimmee

Keep the following information in mind while searching for Hilton Head Island to Kissimmee flight deals. Data was last updated July 31, 2025.

Round-trip from

$342
(American Airlines)

One-way from

$173
(American Airlines)
From Hilton Head Island to Kissimmee
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One-way flight from Hilton Head Island to Kissimmee
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Find flight deals from Hilton Head Island to Kissimmee

Cheapest flights from Hilton Head Island to Kissimmee
Explore the most affordable flight options available from Hilton Head Island to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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 12/236:26 pmHHH - MCO
1 stop5h 48mAmerican Airlines
Mon 12/2912:09 pmMCO - HHH
1 stop5h 20mAmerican Airlines
Deal found 7/30$342

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Kissimmee 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 July 31, 2025.
Use the filters below to find and compare flights from Hilton Head Island to Kissimmee that are best for you.

Fly from

Hilton Head Island

Fly to

Kissimmee

Route

Depart

Return

Price

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Tue 12/23

6:26 pm-12:14 am

1 stop5h 48m

Orlando

Mon 12/29

12:09 pm-5:29 pm

1 stop5h 20m

$342

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Wed 10/29

12:45 pm-11:59 pm

2 stops11h 14m

$173

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 8/10

12:02 pm-7:00 pm

1 stop6h 58m

$1,260

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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

Have a flexible travel schedule? Discover the best time to fly to Kissimmee 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 Kissimmee

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

Currently, May is the cheapest month in which you can book a flight from Hilton Head Island to Kissimmee (average of $206). Flying from Hilton Head Island to Kissimmee in November is currently the most expensive (average of $288). 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 Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated July 31, 2025.
See what other customers who have flown with United Airlines and American Airlines from Hilton Head Island to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,900 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Overall

7.4

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
8,900 reviews
United Airlines
7.4
Good
8,900 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Overall

7.4

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
8,900 reviews

Food

6.6

Entertainment

7.1

Comfort

7.3

Boarding

7.7

Crew

8.1

Overall

7.4

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 Kissimmee. 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 Kissimmee?

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

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

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

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

    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 Kissimmee.

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

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

    Currently, May is the cheapest month in which you can book a flight from Hilton Head Island to Kissimmee (average of $206). Flying from Hilton Head Island to Kissimmee in November is currently the most expensive (average of $288). 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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