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Kissimmee

$186+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
HHH — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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.
Mon 3/22:58 pm
HHH
-
MCO
1 stop4h 04m
American Airlines
Sat 3/75:00 am
MCO
-
HHH
1 stop5h 33m
American Airlines
Deal found 1/28$371
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/1112:51 pm
HHH
-
MCO
1 stop5h 07m
American Airlines
Sun 2/156:00 am
MCO
-
HHH
1 stop4h 33m
American Airlines
Deal found 1/27$507
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Mon 2/166:20 pm
HHH
-
MCO
2 stops13h 33m
American Airlines
Thu 2/196:00 am
MCO
-
HHH
1 stop4h 33m
American Airlines
Deal found 1/28$544
This American Airlines deal was found by Cheapflights users on 1/27. 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 1/2912:51 pm
HHH
-
MCO
1 stop6h 11m
American Airlines
Sun 2/17:00 am
MCO
-
HHH
1 stop5h 20m
American Airlines
Deal found 1/27$602

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$371
(American Airlines)

One-way from

$186
(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.
Search Deals
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 January 29, 2026.
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

Mon 3/2

2:58 pm-7:02 pm

1 stop4h 04m

Orlando

Sat 3/7

5:00 am-10:33 am

1 stop5h 33m

$371

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Wed 2/11

12:51 pm-5:58 pm

1 stop5h 07m

Orlando

Sun 2/15

6:00 am-10:33 am

1 stop4h 33m

$507

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Mon 2/16

6:20 pm-7:53 am

2 stops13h 33m

Orlando

Thu 2/19

6:00 am-10:33 am

1 stop4h 33m

$544

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Thu 2/12

2:58 pm-9:59 pm

1 stop7h 01m

Orlando

Mon 2/16

5:00 am-10:33 am

1 stop5h 33m

$602

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sat 2/28

2:58 pm-7:02 pm

1 stop4h 04m

$186

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Mon 3/2

2:58 pm-11:28 pm

2 stops8h 30m

$191

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Thu 4/16

12:08 pm-5:40 pm

1 stop5h 32m

$240

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Sun 3/1

6:20 pm-7:53 am

2 stops13h 33m

$343

Hilton Head IslandOrlando

HHH - MCO

HHHMCO

Hilton Head Island

Fri 4/3

4:11 pm-11:02 am

1 stop18h 51m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, January is the cheapest month in which you can book a flight from Hilton Head Island to Kissimmee (average of $75). 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 04m. 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, January is the cheapest month in which you can book a flight from Hilton Head Island to Kissimmee (average of $75). 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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