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Kissimmee

$191+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MCO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/316:13 pmHHH - MCO
1 stop3h 47mAmerican Airlines
Sun 1/45:00 amMCO - HHH
1 stop5h 44mAmerican Airlines
Deal found 12/15$546
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/232:46 pmHHH - MCO
1 stop5h 41mAmerican Airlines
Sat 12/272:04 pmMCO - HHH
1 stop3h 39mAmerican Airlines
Deal found 12/16$595

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$191
(American Airlines)
Provider with most accurate pricing for Hilton Head Island-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hilton Head Island-Orlando (ORL) flights.
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From Hilton Head Island to Kissimmee
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One-way flight from Hilton Head Island to Kissimmee
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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 December 18, 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

Thu 1/15

3:29 pm-8:14 pm

1 stop4h 45m

Orlando

Wed 1/21

8:00 am-2:59 pm

1 stop6h 59m

$410

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Thu 1/1

6:13 pm-10:00 pm

1 stop3h 47m

Orlando

Mon 1/5

5:00 am-10:44 am

1 stop5h 44m

$493

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Wed 12/31

6:13 pm-10:00 pm

1 stop3h 47m

Orlando

Sun 1/4

5:00 am-10:44 am

1 stop5h 44m

$546

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Tue 1/20

12:51 pm-5:58 pm

1 stop5h 07m

Orlando

Tue 1/20

7:50 pm-2:59 pm

2 stops19h 09m

$906

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sat 5/2

3:00 pm-9:58 pm

1 stop6h 58m

Orlando

Tue 5/5

7:16 am-2:01 pm

1 stop6h 45m

$1,085

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 1/11

3:29 pm-8:17 am

2 stops16h 48m

$191

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sat 1/10

3:29 pm-9:06 pm

1 stop5h 37m

$198

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 3/8

6:20 pm-7:54 am

2 stops13h 34m

$294

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 6/7

6:24 pm-8:19 am

2 stops13h 55m

$314

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 5/24

6:24 pm-8:19 am

2 stops13h 55m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 11 results
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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, February is the cheapest month in which you can book a flight from Hilton Head Island to Kissimmee (average of $77). Flying from Hilton Head Island to Kissimmee in November is currently the most expensive (average of $134). 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.

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.

  • How long is the flight from Hilton Head Island to Kissimmee?

    American Airlines can get you from Hilton Head Island to Kissimmee in just under 4h 45m. Your travel time can differ by up to . Airlines will cover a distance of 264 mi.

  • 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, February is the cheapest month in which you can book a flight from Hilton Head Island to Kissimmee (average of $77). Flying from Hilton Head Island to Kissimmee in November is currently the most expensive (average of $134). 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.

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