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Hilton Head Island

$175+ Cheap flights from Orlando (MCO) 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — HHH
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheap flight deals from Orlando to Hilton Head Island

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) to Hilton Head Island (HHH). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$416
(American Airlines)

One-way from

$175
(American Airlines)
Provider with most accurate pricing for Orlando-Hilton Head Island flight deals.
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Provider most trusted by Cheapflights users for Orlando-Hilton Head Island flights.
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From Orlando to Hilton Head Island
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One-way flight from Orlando to Hilton Head Island
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Find flight deals from Orlando to Hilton Head Island

Cheapest flights from Orlando to Hilton Head Island
Explore the most affordable flight options available from Orlando to Hilton Head Island. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This American Airlines deal was found by Cheapflights users on 10/15. 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.
Mon 11/36:22 pmMCO - HHH
2 stops18h 07mAmerican Airlines
Wed 11/53:27 pmHHH - MCO
1 stop5h 36mAmerican Airlines
Deal found 10/15$416
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/56:00 amMCO - HHH
1 stop6h 29mAmerican Airlines
Fri 11/77:14 pmHHH - MCO
1 stop4h 28mAmerican Airlines
Deal found 10/15$434
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/36:22 pmMCO - HHH
2 stops18h 07mAmerican Airlines
Fri 11/77:14 pmHHH - MCO
1 stop4h 28mAmerican Airlines
Deal found 10/16$441
This American Airlines deal was found by Cheapflights users on 10/16. 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 10/319:37 amMCO - HHH
1 stop5h 25mAmerican Airlines
Fri 11/77:14 pmHHH - MCO
1 stop4h 28mAmerican Airlines
Deal found 10/16$446
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/146:00 amMCO - HHH
2 stops12h 37mAmerican Airlines
Fri 11/216:40 pmHHH - MCO
2 stops13h 36mAmerican Airlines
Deal found 10/15$448
This American Airlines deal was found by Cheapflights users on 10/16. 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 10/318:28 amMCO - HHH
1 stop6h 34mAmerican Airlines
Tue 11/41:02 pmHHH - MCO
1 stop6h 09mAmerican Airlines
Deal found 10/16$455
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/16:15 amMCO - HHH
1 stop5h 17mAmerican Airlines
Fri 11/77:14 pmHHH - MCO
1 stop4h 28mAmerican Airlines
Deal found 10/16$464
This American Airlines deal was found by Cheapflights users on 10/15. 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 11/56:00 amMCO - HHH
2 stops8h 57mAmerican Airlines
Wed 11/57:07 pmHHH - MCO
2 stops13h 09mAmerican Airlines
Deal found 10/15$466
This American Airlines deal was found by Cheapflights users on 10/16. 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 11/36:22 pmMCO - HHH
2 stops18h 07mAmerican Airlines
Thu 11/62:51 pmHHH - MCO
1 stop3h 55mAmerican Airlines
Deal found 10/16$471

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando 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 October 16, 2025.
Use the filters below to find and compare flights from Orlando Airport to Hilton Head Island that are best for you.

Fly from

Orlando

Fly to

Hilton Head Island

Route

Depart

Return

Price

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 11/3

6:22 pm-12:29 pm

2 stops18h 07m

Hilton Head Island

Wed 11/5

3:27 pm-9:03 pm

1 stop5h 36m

$416

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 11/4

6:22 pm-10:58 am

2 stops16h 36m

Hilton Head Island

Wed 11/5

7:07 pm-11:42 pm

1 stop4h 35m

$416

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 11/5

6:00 am-12:29 pm

1 stop6h 29m

Hilton Head Island

Fri 11/7

7:14 pm-11:42 pm

1 stop4h 28m

$434

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 11/3

6:22 pm-12:29 pm

2 stops18h 07m

Hilton Head Island

Fri 11/7

7:14 pm-11:42 pm

1 stop4h 28m

$441

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 11/14

6:00 am-6:37 pm

2 stops12h 37m

Hilton Head Island

Fri 11/21

6:40 pm-8:16 am

2 stops13h 36m

$448

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Thu 10/30

6:00 am-4:51 pm

2 stops10h 51m

Hilton Head Island

Mon 11/3

7:07 pm-8:16 am

2 stops13h 09m

$455

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Fri 10/31

8:28 am-3:02 pm

1 stop6h 34m

Hilton Head Island

Wed 11/5

7:07 pm-11:42 pm

1 stop4h 35m

$455

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Tue 11/4

6:22 pm-10:58 am

2 stops16h 36m

Hilton Head Island

Fri 11/7

7:14 pm-8:16 am

2 stops13h 02m

$462

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Wed 11/5

6:00 am-2:57 pm

2 stops8h 57m

Hilton Head Island

Wed 11/5

7:07 pm-8:16 am

2 stops13h 09m

$466

OrlandoHilton Head Island

MCO - HHH

MCOHHH

Orlando

Mon 11/3

6:22 pm-12:29 pm

2 stops18h 07m

Hilton Head Island

Thu 11/6

2:51 pm-6:46 pm

1 stop3h 55m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 16 results
1
2

Compare providers for flights from Orlando to Hilton Head Island

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Hilton Head Island in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Orlando Airport-Hilton Head Island flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Hilton Head Island flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando Airport-Hilton Head Island flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Airport-Hilton Head Island flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Orlando Airport-Hilton Head Island flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Orlando to Hilton Head Island

Have a flexible travel schedule? Discover the best time to fly to Hilton Head Island from Orlando 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 Orlando Airport to Hilton Head Island

What is the cheapest month to book a flight from Orlando Airport to Hilton Head Island?

Currently, February is the cheapest month in which you can book a flight from Orlando Airport to Hilton Head Island (average of $63). Flying from Orlando Airport to Hilton Head Island in April is currently the most expensive (average of $139). 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 MCO to HHH?

Find hourly flight availability from Orlando 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 October 16, 2025.

A simple way to save on the total cost of your ticket is to fly from Orlando Airport to Hilton Head Island in the evening. If you’re flexible enough to do this you can expect to save up to 80% on your trip compared to booking a flight at noon.

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 October 16, 2025.
Read reviews from past customers who have flown American Airlines from Orlando Airport 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
11,043 reviews

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Comfort

7.2

Overall

7.2

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
11,043 reviews
American Airlines
7.2
Good
11,043 reviews

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Comfort

7.2

Overall

7.2

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 Orlando 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 Orlando?

    Located just 3.3 mi from the city center, Hilton Head Island is the airport most travelers will use when flying to Hilton Head Island from Orlando. Booking flights from Orlando to Hilton Head (HHH) should be relatively easy as there are 0 daily inbound flights from Orlando from 1 airline.

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

    There are many flights that can get you from Orlando Airport to Hilton Head Island in 18h 07m. Fly via American Airlines to get the fastest option. The distance between Orlando Airport and Hilton Head Island is about 264 mi.

  • What is the cheapest airline to fly from Orlando Airport to Hilton Head Island round-trip?

    American Airlines, at $306, was found to be the cheapest airline from Orlando Airport to Hilton Head Island..

  • Can I find deals for flights from Orlando to Hilton Head Island that include hotel bookings?

    Yes. In addition to deals on Orlando to Hilton Head Island flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando 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 Orlando to Hilton Head Island.

  • Can I find deals for business class flights from Orlando to Hilton Head Island?

    Yes. Cheapflights offers flight deals from Orlando 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 Orlando Airport to Hilton Head Island?

    Currently, February is the cheapest month in which you can book a flight from Orlando Airport to Hilton Head Island (average of $63). Flying from Orlando Airport to Hilton Head Island in April is currently the most expensive (average of $139). 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
Bluffton

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Top airline flying from Orlando to Hilton Head Island

Discover the top airline that operate flights from Orlando 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$306Average$361FlexibilityNo cancel feeOn-time71%

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