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Kissimmee

$164+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MCO
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
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 September 15, 2025.

Round-trip from

$317
(American Airlines)

One-way from

$164
(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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 10/155:21 pmHHH - MCO
1 stop4h 16mAmerican Airlines
Sun 10/195:00 amMCO - HHH
1 stop6h 32mAmerican Airlines
Deal found 9/15$317
This American Airlines deal was found by Cheapflights users on 9/13. 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 11/31:02 pmHHH - MCO
1 stop6h 09mAmerican Airlines
Wed 11/511:10 amMCO - HHH
1 stop3h 47mAmerican Airlines
Deal found 9/13$327
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 11/96:40 pmHHH - MCO
2 stops13h 29mAmerican Airlines
Fri 11/147:00 amMCO - HHH
2 stops11h 37mAmerican Airlines
Deal found 9/15$370
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/93:02 pmHHH - MCO
1 stop5h 15mAmerican Airlines
Sat 10/118:35 pmMCO - HHH
2 stops14h 57mAmerican Airlines
Deal found 9/15$385
This American Airlines deal was found by Cheapflights users on 9/14. 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 9/2912:56 pmHHH - MCO
1 stop7h 01mAmerican Airlines
Fri 10/311:18 amMCO - HHH
1 stop5h 29mAmerican Airlines
Deal found 9/14$419
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/75:21 pmHHH - MCO
1 stop6h 08mAmerican Airlines
Fri 10/106:15 amMCO - HHH
1 stop5h 17mAmerican Airlines
Deal found 9/14$473

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 September 15, 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

Wed 10/15

5:21 pm-9:37 pm

1 stop4h 16m

Orlando

Sun 10/19

5:00 am-11:32 am

1 stop6h 32m

$317

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 11/9

6:40 pm-12:24 am

1 stop5h 44m

Orlando

Fri 11/14

12:12 pm-6:37 pm

1 stop6h 25m

$327

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Mon 11/3

1:02 pm-7:11 pm

1 stop6h 09m

Orlando

Wed 11/5

11:10 am-2:57 pm

1 stop3h 47m

$327

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Thu 10/9

3:02 pm-8:17 pm

1 stop5h 15m

Orlando

Sat 10/11

8:35 pm-11:32 am

2 stops14h 57m

$385

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Mon 9/29

12:56 pm-7:57 pm

1 stop7h 01m

Orlando

Fri 10/3

11:18 am-4:47 pm

1 stop5h 29m

$419

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sat 3/14

6:25 pm-12:12 am

1 stop5h 47m

Orlando

Wed 3/18

9:10 am-2:19 pm

1 stop5h 09m

$437

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Wed 10/15

5:21 pm-11:29 pm

1 stop6h 08m

$164

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Fri 10/3

3:26 pm-8:14 pm

1 stop4h 48m

$210

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 10/19

3:02 pm-8:58 pm

1 stop5h 56m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 $289). 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 16m. 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, 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 $289). 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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