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Kissimmee

$212+ Cheap flights from Maui 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 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MCO
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Maui to Kissimmee

Best flights from Maui to Kissimmee
Discover carefully curated flight deals from Maui to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 1, 2026.

This American Airlines deal was found by Cheapflights users on 12/30. 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.
Thu 2/57:00 pmOGG - MCO
1 stop10h 44mAmerican Airlines
Tue 2/105:30 amMCO - OGG
1 stop12h 44mAmerican Airlines
Deal found 12/30$419
This Alaska Airlines deal was found by Cheapflights users on 12/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1711:54 pmOGG - MCO
1 stop24h 46mAlaska Airlines
Thu 2/197:44 amMCO - OGG
1 stop21h 02mAlaska Airlines
Deal found 12/29$481
This Alaska Airlines deal was found by Cheapflights users on 12/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/511:21 amOGG - MCO
2 stops13h 14mMultiple Airlines
Tue 2/107:00 amMCO - OGG
2 stops18h 30mMultiple Airlines
Deal found 12/30$506
This Delta deal was found by Cheapflights users on 12/31. 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 1/169:05 pmOGG - MCO
1 stop15h 45mDelta
Tue 1/207:00 amMCO - OGG
1 stop17h 15mDelta
Deal found 12/31$522

Find flight deals from Maui to Kissimmee

Keep the following information in mind while searching for Maui to Kissimmee flight deals. Data was last updated January 1, 2026.

Round-trip from

$419
(American Airlines)

One-way from

$212
(Delta)
From Maui to Kissimmee
Search Deals
One-way flight from Maui to Kissimmee
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Maui 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 1, 2026.
Use the filters below to find and compare flights from Maui to Kissimmee that are best for you.

Fly from

Maui

Fly to

Kissimmee

Route

Depart

Return

Price

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Thu 2/5

7:00 pm-10:44 am

1 stop10h 44m

Orlando

Tue 2/10

5:30 am-1:14 pm

1 stop12h 44m

$419

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Tue 2/17

11:54 pm-5:40 am

1 stop24h 46m

Orlando

Thu 2/19

7:44 am-11:46 pm

1 stop21h 02m

$481

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Thu 2/5

11:21 am-5:35 am

2 stops13h 14m

Orlando

Tue 2/10

7:00 am-8:30 pm

2 stops18h 30m

$506

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Fri 1/16

9:05 pm-5:50 pm

1 stop15h 45m

Orlando

Tue 1/20

7:00 am-7:15 pm

1 stop17h 15m

$522

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Tue 4/28

12:40 pm-7:20 am

1 stop12h 40m

$212

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Tue 4/14

1:08 pm-6:54 am

1 stop11h 46m

$212

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Tue 4/14

9:59 pm-4:54 pm

1 stop12h 55m

$226

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Mon 4/13

11:02 pm-5:03 pm

1 stop12h 01m

$226

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Sat 5/9

8:12 pm-6:02 pm

1 stop15h 50m

$250

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Sat 5/9

6:20 pm-6:27 pm

2 stops18h 07m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 11 results
1
2

Best time to book a flight from Maui to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Maui 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 Maui to Kissimmee

What is the cheapest month to book a flight from Maui to Kissimmee?

Currently, October is the cheapest month in which you can book a flight from Maui to Kissimmee (average of $224). Flying from Maui to Kissimmee in July is currently the most expensive (average of $663). 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.

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated January 1, 2026.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and United Airlines from Maui to Kissimmee to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,597 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Alaska Airlines
8.0
Very good
11,597 reviews
Alaska Airlines
8.0
Very good
11,597 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
Delta
7.9
Good
8,013 reviews
Alaska Airlines
8.0
Very good
11,597 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
United Airlines
7.4
Good
9,129 reviews
Alaska Airlines
8.0
Very good
11,597 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.
American Airlines
7.2
Good
11,069 reviews
Alaska Airlines
8.0
Very good
11,597 reviews

Comfort

7.8

Overall

8.0

Crew

8.5

Entertainment

7.0

Food

7.1

Boarding

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Dec 2025

SEA - MSY

I really got a lesson in upgrades. I let my seat get chosen . Both times a middle seat...on purpose ...even when we were not full. That's petty I sat behind the first class . They got more than 1 drink ...and a snack . .and the staff actually talked to them...behind a see thru shawl/sheet in the aisle....... You could see over the seats just fine and you could hear the voices just fine. But the sheet let You KNOW. Your not welcome here. For a moment I regretted not spending 300 dollars per seat so I could see a smile and eat a sandwhich and enjoy my seat . The married couple drank champain and laughed and flirted with each other. It looked so happy and care free MONEY really does buy happiness ..the hateful glares and sighs from my seat mates brought me back to reality I wasn't rich and I still had 2 hours left in this middle seat.

Related info for your journey

Find useful and relevant information for your journey from Maui to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Maui to Kissimmee?

    There are many flights that can get you from Maui to Kissimmee in 10h 44m. Fly via American Airlines to get the fastest option. Airlines will cover a distance of 4669 mi.

  • What are the cheapest airlines to fly from Maui to Kissimmee one-way?

    For one-way options, check prices for Alaska Airlines. According to our data, you can fly for as low as $199. Users have also found prices from $214 and $224 on American Airlines and Delta, respectively.

  • Can I find deals for flights from Maui to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Maui to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Maui to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Maui to Kissimmee.

  • Can I find deals for business class flights from Maui to Kissimmee?

    Yes. Cheapflights offers flight deals from Maui 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 Maui to Kissimmee?

    Currently, October is the cheapest month in which you can book a flight from Maui to Kissimmee (average of $224). Flying from Maui to Kissimmee in July is currently the most expensive (average of $663). 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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Top 4 airlines flying from Maui to Kissimmee

Discover the top 4 airlines that operate flights from Maui to Kissimmee. 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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$224Average$567FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$400Average$572FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$418Average$606FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$419Average$651FlexibilityNo cancel feeOn-time69%

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