$220+ Cheap flights from Kissimmee, FL to Hilton Head Island (HHH)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Oct 20 — Oct 271
Round-trip
1 adult, Economy
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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
Best
Last-minute
One-way
Cheapest flights from Kissimmee to Hilton Head IslandExplore 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 September 20, 2026.
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 September 20, 2026.
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 11/137:58 am -
1 stop6h 23m
Sun 11/155:54 pm -
1 stop6h 27m
Deal found 9/16![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/236:05 am -
1 stop5h 00m
Fri 10/302:56 pm -
2 stops17h 06m
Deal found 9/18![American Airlines logo]()
$445
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 10/157:00 am -
1 stop4h 05m
Wed 10/212:56 pm -
1 stop6h 00m
Deal found 9/15![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/27:00 am -
1 stop6h 45m
Tue 10/612:29 pm -
1 stop6h 44m
Deal found 9/17![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/17:00 am -
1 stop6h 45m
Sat 10/106:13 pm -
1 stop3h 47m
Deal found 9/16![American Airlines logo]()
$478
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/17:00 am -
1 stop6h 45m
Mon 10/52:56 pm -
1 stop5h 03m
Deal found 9/16![American Airlines logo]()
$508
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 9/308:03 am -
1 stop4h 12m
Sat 10/35:15 pm -
1 stop4h 42m
Deal found 9/16![American Airlines logo]()
$611
Best flights from Kissimmee to Hilton Head IslandDiscover carefully curated flight deals from Kissimmee to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
Discover carefully curated flight deals from Kissimmee to Hilton Head Island that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 20, 2026.
This American Airlines deal was found by Cheapflights users on 9/19. 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 11/1310:14 am -
1 stop6h 56m
Sun 11/155:54 pm -
1 stop6h 27m
Deal found 9/19![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/197:00 am -
1 stop4h 05m
Mon 10/266:08 pm -
1 stop6h 24m
Deal found 9/19![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/37:00 am -
1 stop6h 50m
Wed 10/711:36 am -
1 stop6h 54m
Deal found 9/18![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/27:00 am -
1 stop6h 45m
Tue 10/612:29 pm -
1 stop6h 44m
Deal found 9/17![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/17:00 am -
1 stop6h 45m
Mon 10/52:56 pm -
1 stop5h 03m
Deal found 9/16![American Airlines logo]()
$508
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 10/157:15 am -
2 stops10h 23m
Wed 10/212:56 pm -
1 stop5h 03m
Deal found 9/15![American Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 9/19. 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 3/15:00 am -
1 stop5h 33m
Sat 3/66:22 pm -
2 stops13h 32m
Deal found 9/19![American Airlines logo]()
$533
Last-minute flights from Kissimmee to Hilton Head IslandDiscover last-minute flight deals from Kissimmee to Hilton Head Island. Data last updated September 20, 2026 and is based on user searches.
Discover last-minute flight deals from Kissimmee to Hilton Head Island. Data last updated September 20, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 9/308:03 am -
1 stop4h 12m
Sat 10/35:15 pm -
1 stop4h 42m
Deal found 9/16![American Airlines logo]()
$611
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/17:00 am -
1 stop6h 45m
Sat 10/106:13 pm -
1 stop3h 47m
Deal found 9/16![American Airlines logo]()
$478
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/17:00 am -
1 stop6h 45m
Mon 10/52:56 pm -
1 stop5h 03m
Deal found 9/16![American Airlines logo]()
$508
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/27:00 am -
1 stop6h 45m
Tue 10/612:29 pm -
1 stop6h 44m
Deal found 9/17![American Airlines logo]()
$477
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/46:00 am -
1 stop5h 18m
Thu 10/82:56 pm -
1 stop7h 04m
Deal found 9/19![American Airlines logo]()
$621
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 10/157:00 am -
1 stop4h 05m
Wed 10/212:56 pm -
1 stop6h 00m
Deal found 9/15![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 9/19. 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 10/197:00 am -
1 stop4h 05m
Mon 10/266:08 pm -
1 stop6h 24m
Deal found 9/19![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 9/18. 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 10/236:05 am -
1 stop5h 00m
Fri 10/302:56 pm -
2 stops17h 06m
Deal found 9/18![American Airlines logo]()
$445
One-way flights from Kissimmee to Hilton Head IslandSearch for one-way flight options from Kissimmee to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
Search for one-way flight options from Kissimmee to Hilton Head Island. Find affordable one-way fares based on user searches. Data last updated September 20, 2026.
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.
Fri 11/612:32 pm -
1 stop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$220
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 10/196:05 am -
1 stop5h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$248
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/187:00 am -
1 stop4h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/171:55 pm -
1 stop21h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/17. 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 10/19:32 am -
1 stop4h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/176:13 pm -
2 stops16h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 9/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:05 am -
1 stop6h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Delta logo]()
$410
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Fri 9/256:00 am -
2 stops10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$415
This United Airlines deal was found by Cheapflights users on 9/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/16:20 pm -
2 stops18h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![United Airlines logo]()
$591
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 September 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $397 (American Airlines) |
One-way from | $220 (American Airlines) |
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 7,457,451 searches. Data last updated September 20, 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
Cheapest round-trip
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Fri 11/6
12:32 pm-5:10 pm
1 stop4h 38m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$220
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Mon 10/19
6:05 am-11:05 am
1 stop5h 00m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$248
Quickest round-trip
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Sun 10/18
7:00 am-11:05 am
1 stop4h 05m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$256
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Sat 10/17
1:55 pm-11:43 am
1 stop21h 48m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$279
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Thu 10/1
9:32 am-1:45 pm
1 stop4h 13m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Sat 10/17
6:13 pm-11:05 am
2 stops16h 52m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$365
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Fri 11/13
10:14 am-5:10 pm
1 stop6h 56m
Hilton Head Island
Sun 11/15
5:54 pm-12:21 am
1 stop6h 27m
$397
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Mon 10/19
7:00 am-11:05 am
1 stop4h 05m
Hilton Head Island
Mon 10/26
6:08 pm-12:32 am
1 stop6h 24m
$397
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Fri 9/25
9:05 am-3:27 pm
1 stop6h 22m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$410
OrlandoHilton Head Island
MCO Orlando - HHH Hilton Head Island
MCOHHH
Orlando
Thu 10/1
11:05 am-3:27 pm
1 stop4h 22m
Hilton Head Island
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$410
Showing 1-10 of 17 resultsSorted by cheapest first
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.
MCO-HHH
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
K1S-HHH
MCO-HHH
No data available for this route at this time. Please check back soon.
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.
Traveling to a place near Hilton Head Island?
Book flights to Hilton Head Island if you plan to visit one of these locationsBeaufort
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Complete your trip
Complete your trip to Hilton Head Island by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Kissimmee to Hilton Head Island, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Hilton Head Island
Explore flights to Hilton Head Island departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on September 20, 2026.
Kissimmee and Hilton Head Island flights
Browse other Kissimmee and Hilton Head Island flight options. Last updated on September 20, 2026.
Popular flight searches
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Kissimmee to Hilton Head Island flights
Consider these flights traveling from Kissimmee to Hilton Head Island.
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 7,457,451 searches. Data last updated September 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$326 | Average$446 | FlexibilityNo cancel fee | On-time71% |