Kissimmee

$215+ 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
OGG — MCO
Mar 22 — Mar 291
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Cheap flight deals from Maui to Kissimmee

Cheapest flights from Maui to Kissimmee
Explore the most affordable flight options available from Maui to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2026.

This Expedia deal was found by Cheapflights users on 2/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:02 pm
OGG
-
MCO
1 stop24h 50m
Multiple Airlines
Thu 4/237:27 pm
MCO
-
OGG
1 stop20h 24m
Multiple Airlines
Deal found 2/19$450
This United Airlines deal was found by Cheapflights users on 2/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:05 pm
OGG
-
MCO
1 stop12h 22m
United Airlines
Fri 5/88:00 am
MCO
-
OGG
1 stop13h 15m
United Airlines
Deal found 2/17$492
This American Airlines deal was found by Cheapflights users on 2/17. 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 4/309:45 pm
OGG
-
MCO
1 stop13h 09m
American Airlines
Fri 5/89:30 am
MCO
-
OGG
2 stops16h 26m
American Airlines
Deal found 2/17$536
This United Airlines deal was found by Cheapflights users on 2/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:50 pm
OGG
-
MCO
1 stop11h 20m
United Airlines
Sun 3/88:00 am
MCO
-
OGG
1 stop13h 51m
United Airlines
Deal found 2/17$568
This Expedia deal was found by Cheapflights users on 2/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:02 pm
OGG
-
MCO
1 stop24h 50m
Multiple Airlines
Sun 4/267:00 am
MCO
-
OGG
2 stops21h 10m
Multiple Airlines
Deal found 2/18$576
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Sun 3/111:55 pm
OGG
-
MCO
1 stop12h 00m
American Airlines
Thu 3/510:25 am
MCO
-
OGG
2 stops17h 00m
American Airlines
Deal found 2/18$579
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Sun 3/12:25 pm
OGG
-
MCO
1 stop11h 36m
United Airlines
Thu 3/56:23 am
MCO
-
OGG
1 stop16h 08m
United Airlines
Deal found 2/18$594
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Sun 4/197:35 pm
OGG
-
MCO
1 stop13h 59m
United Airlines
Sun 4/268:00 am
MCO
-
OGG
1 stop14h 52m
United Airlines
Deal found 2/18$596

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 February 20, 2026.

Round-trip from

$450
(Expedia)

One-way from

$215
(Delta)
From Maui to Kissimmee
One-way flight from Maui to Kissimmee

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 February 20, 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

Sun 4/19

11:02 pm-5:52 am

1 stop24h 50m

Orlando

Thu 4/23

7:27 pm-9:51 am

1 stop20h 24m

$450

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Thu 4/30

2:05 pm-8:27 am

1 stop12h 22m

Orlando

Fri 5/8

8:00 am-3:15 pm

1 stop13h 15m

$492

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Thu 4/30

9:45 pm-5:16 pm

2 stops13h 31m

Orlando

Fri 5/8

9:30 am-7:56 pm

2 stops16h 26m

$541

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Wed 3/4

5:50 pm-10:10 am

1 stop11h 20m

Orlando

Sun 3/8

8:00 am-3:51 pm

1 stop13h 51m

$568

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Sun 4/19

11:02 pm-5:52 am

1 stop24h 50m

Orlando

Sun 4/26

7:00 am-10:10 pm

2 stops21h 10m

$576

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Sun 4/19

7:35 pm-3:34 pm

1 stop13h 59m

Orlando

Sun 4/26

8:00 am-4:52 pm

1 stop14h 52m

$596

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Mon 3/2

2:04 pm-5:40 am

1 stop10h 36m

Orlando

Wed 3/4

7:44 am-11:46 pm

1 stop21h 02m

$603

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Wed 3/4

2:04 pm-5:40 am

1 stop10h 36m

Orlando

Sun 3/8

7:44 am-10:46 pm

1 stop21h 02m

$618

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Sat 3/7

2:25 pm-6:55 am

1 stop11h 30m

Orlando

Wed 3/11

9:00 am-7:43 pm

2 stops16h 43m

$618

KahuluiOrlando

OGG - MCO

OGGMCO

Kahului

Wed 3/4

7:21 am-5:40 am

2 stops17h 19m

Orlando

Sun 3/8

7:44 am-10:46 pm

1 stop21h 02m

$624

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

Showing 1-10 of 21 results
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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 February 20, 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.

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

Entertainment

7.0

Boarding

8.1

Crew

8.5

Overall

8.0

Comfort

7.8

Food

7.1

Reviews

1 / 20
10.0
Excellent

robert,Feb 2026

LAS - SAN

The good customer service team made you fell welcome on the flight.

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 12h 22m. Fly via United Airlines or American Airlines to get the fastest option. Airlines will cover a distance of 4669 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $209. Users have also found prices from $214 and $216 on American Airlines and Alaska Airlines, 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$224Average$567FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$418Average$628FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$452Average$591FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$479Average$607FlexibilityNo cancel feeOn-time75%

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