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Hilton Head Island

$198+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 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 12/316:00 amMCO - HHH
1 stop4h 44mAmerican Airlines
Sun 1/46:13 pmHHH - MCO
1 stop6h 16mAmerican Airlines
Deal found 12/15$493
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 12/232:04 pmMCO - HHH
1 stop3h 39mAmerican Airlines
Fri 12/266:13 pmHHH - MCO
1 stop6h 16mAmerican Airlines
Deal found 12/16$560
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.
Sat 12/272:04 pmMCO - HHH
1 stop3h 39mAmerican Airlines
Wed 12/316:13 pmHHH - MCO
1 stop3h 47mAmerican Airlines
Deal found 12/16$658

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$340
(American Airlines)

One-way from

$198
(American Airlines)
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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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 December 18, 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

Wed 1/28

8:00 am-12:20 pm

1 stop4h 20m

Hilton Head Island

Mon 2/2

3:29 pm-8:17 am

2 stops16h 48m

$340

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 1/31

9:03 am-2:59 pm

1 stop5h 56m

Hilton Head Island

Tue 2/3

3:29 pm-8:14 pm

1 stop4h 45m

$363

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Thu 1/1

8:00 am-2:16 pm

1 stop6h 16m

Hilton Head Island

Mon 1/5

11:14 am-3:27 pm

1 stop4h 13m

$493

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 12/31

6:00 am-10:44 am

1 stop4h 44m

Hilton Head Island

Sun 1/4

6:13 pm-12:29 am

1 stop6h 16m

$493

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 12/23

2:04 pm-5:43 pm

1 stop3h 39m

Hilton Head Island

Fri 12/26

6:13 pm-12:29 am

1 stop6h 16m

$560

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sat 1/31

9:03 am-2:59 pm

1 stop5h 56m

$198

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 6/10

6:34 am-3:44 pm

2 stops9h 10m

$268

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 6/10

11:15 am-11:12 am

3 stops23h 57m

$343

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 12/23

7:18 pm-10:44 am

2 stops15h 26m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, February is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $63). Flying from Kissimmee to Hilton Head Island in March is currently the most expensive (average of $118). 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 December 18, 2025.

One of the essential ways to save on airfare from Kissimmee to Hilton Head Island is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 81% on airfare.

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 December 18, 2025.
Read reviews from past customers who have flown American Airlines from Kissimmee to Hilton Head Island. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,054 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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.

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

    Departing from Kissimmee to Hilton Head Island will take you 4h 20m. Airlines will cover a distance of 264 mi.

  • 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, February is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $63). Flying from Kissimmee to Hilton Head Island in March is currently the most expensive (average of $118). 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 Hilton Head Island?

Book flights to Hilton Head Island if you plan to visit one of these locations
Beaufort

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Alternative routes for Kissimmee to Hilton Head Island

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$366FlexibilityNo cancel feeOn-time71%

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