HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Hilton Head Island

$186+ 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
May 2 — May 91
Sat 5/2
Sat 5/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Hilton Head Island with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 2, 2026.

This American Airlines deal was found by Cheapflights users on 3/29. 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 6/296:15 am
MCO
-
HHH
1 stop4h 55m
American Airlines
Fri 7/32:48 pm
HHH
-
MCO
1 stop5h 13m
American Airlines
Deal found 3/29$367
This American Airlines deal was found by Cheapflights users on 4/2. 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 4/3012:53 pm
MCO
-
HHH
1 stop5h 16m
American Airlines
Thu 5/71:08 pm
HHH
-
MCO
1 stop5h 53m
American Airlines
Deal found 4/2$377
This American Airlines deal was found by Cheapflights users on 4/2. 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 7/236:15 am
MCO
-
HHH
1 stop4h 55m
American Airlines
Sun 7/2611:40 am
HHH
-
MCO
1 stop7h 04m
American Airlines
Deal found 4/2$397
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Mon 4/206:00 am
MCO
-
HHH
1 stop6h 37m
American Airlines
Wed 4/222:58 pm
HHH
-
MCO
1 stop7h 01m
American Airlines
Deal found 3/30$407
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/146:00 am
MCO
-
HHH
1 stop4h 47m
American Airlines
Sat 4/186:50 pm
HHH
-
MCO
1 stop5h 24m
American Airlines
Deal found 3/30$447
This American Airlines deal was found by Cheapflights users on 3/30. 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 4/2110:00 am
MCO
-
HHH
1 stop4h 24m
American Airlines
Sat 4/256:50 pm
HHH
-
MCO
1 stop5h 24m
American Airlines
Deal found 3/30$457
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Fri 6/199:00 am
MCO
-
HHH
1 stop5h 13m
American Airlines
Sun 6/212:43 pm
HHH
-
MCO
1 stop6h 17m
American Airlines
Deal found 4/1$460
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 4/229:00 am
MCO
-
HHH
2 stops9h 09m
American Airlines
Sat 4/256:50 pm
HHH
-
MCO
1 stop5h 24m
American Airlines
Deal found 3/30$462
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 4/2211:38 am
MCO
-
HHH
1 stop6h 31m
American Airlines
Fri 4/2411:03 am
HHH
-
MCO
1 stop6h 49m
American Airlines
Deal found 3/30$481
This American Airlines deal was found by Cheapflights users on 3/29. 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 6/106:15 am
MCO
-
HHH
1 stop4h 55m
American Airlines
Sat 6/205:18 pm
HHH
-
MCO
1 stop4h 42m
American Airlines
Deal found 3/29$485

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 April 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$367
(American Airlines)

One-way from

$186
(Delta)
Provider with most accurate pricing for Orlando (ORL)-Hilton Head Island flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Hilton Head Island flights.
Search Deals
From Kissimmee to Hilton Head Island
Search Deals
One-way flight from Kissimmee to Hilton Head Island
Search Deals

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 April 2, 2026.
Use the filters below to find and compare flights from Kissimmee to Hilton Head Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 6/29

6:15 am-11:10 am

1 stop4h 55m

Hilton Head Island

Fri 7/3

2:48 pm-8:01 pm

1 stop5h 13m

$367

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Thu 4/30

12:53 pm-6:09 pm

1 stop5h 16m

Hilton Head Island

Thu 5/7

1:08 pm-7:01 pm

1 stop5h 53m

$377

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 4/22

9:00 am-6:09 pm

2 stops9h 09m

Hilton Head Island

Sat 4/25

6:50 pm-12:14 am

1 stop5h 24m

$462

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 5/26

6:00 am-2:13 pm

2 stops8h 13m

Hilton Head Island

Wed 5/27

2:43 pm-11:59 pm

2 stops9h 16m

$489

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 6/10

6:00 am-4:32 pm

2 stops10h 32m

Hilton Head Island

Sat 6/20

5:18 pm-10:00 pm

1 stop4h 42m

$490
Quickest round-trip

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Sun 4/19

1:47 pm-6:09 pm

1 stop4h 22m

Hilton Head Island

Thu 4/23

2:58 pm-7:04 pm

1 stop4h 06m

$494

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 6/19

6:00 am-2:13 pm

2 stops8h 13m

Hilton Head Island

Sun 6/21

12:56 pm-5:43 pm

1 stop4h 47m

$541

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 4/14

6:00 am-10:47 am

1 stop4h 47m

Hilton Head Island

Mon 4/20

6:39 pm-12:14 am

1 stop5h 35m

$547

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 4/20

9:00 am-3:20 pm

1 stop6h 20m

Hilton Head Island

Wed 4/22

12:08 pm-5:40 pm

1 stop5h 32m

$559

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 4/13

11:00 am-3:20 pm

1 stop4h 20m

Hilton Head Island

Fri 4/17

12:08 pm-6:45 pm

1 stop6h 37m

$581

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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, August is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $70). Flying from Kissimmee to Hilton Head Island in December is currently the most expensive (average of $113). 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 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 55m. 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, August is the cheapest month in which you can book a flight from Kissimmee to Hilton Head Island (average of $70). Flying from Kissimmee to Hilton Head Island in December is currently the most expensive (average of $113). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kissimmee to Hilton Head Island

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to Charlotte flights
Tampa to Charlotte flights
Orlando to Charlotte flights
Miami to Charlotte flights
West Palm Beach to Charlotte flights
Fort Lauderdale to Charleston flights
Miami to Charleston flights
Fort Myers to Charlotte flights
Jacksonville to Charlotte flights
Tampa to Charleston flights
Tampa to Greenville flights
Tampa to Myrtle Beach flights
Orlando to Charleston flights
Miami to Savannah flights
Tallahassee to Charlotte flights
Pensacola to Charlotte flights
Orlando to Myrtle Beach flights
West Palm Beach to Charleston flights
West Palm Beach to Savannah flights
Jacksonville to Greenville flights
Pensacola to Charleston flights
Sarasota to Charlotte flights
Sarasota to Charleston flights
Miami to Greenville flights
West Palm Beach to Greenville flights
Fort Myers to Greenville flights
Orlando to Savannah flights
Fort Lauderdale to Myrtle Beach flights
Fort Myers to Charleston flights
Fort Lauderdale to Savannah flights
Orlando to Greenville flights
Tampa to Savannah flights
Fort Myers to Savannah flights
West Palm Beach to Myrtle Beach flights
Miami to Myrtle Beach flights
Fort Lauderdale to Greenville flights
Sarasota to Savannah flights
Fort Myers to Myrtle Beach flights
Orlando to Columbia flights
Tampa to Columbia flights
Miami to Columbia flights
West Palm Beach to Augusta flights
Key West to Charlotte flights
West Palm Beach to Columbia flights
Miami to Augusta flights
Pensacola to Savannah flights
Panama City to Charleston flights
Gainesville to Charlotte flights
Melbourne to Charlotte flights

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 April 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$260Average$371FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.