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Kissimmee

$321+ Cheap flights from Midland (MAF) to Kissimmee, FL

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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MCO
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Midland to Kissimmee

Cheapest flights from Midland to Kissimmee
Explore the most affordable flight options available from Midland to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 12/2612:22 pmMAF - MCO
1 stop7h 52mAmerican Airlines
Sun 1/115:30 amMCO - MAF
1 stop5h 37mAmerican Airlines
Deal found 12/16$692
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/267:35 amMAF - MCO
1 stop6h 30mSouthwest
Sun 1/1111:00 amMCO - MAF
2 stops11h 20mSouthwest
Deal found 12/16$697
This Southwest deal was found by Cheapflights users on 12/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:45 pmMAF - MCO
1 stop7h 10mSouthwest
Sat 1/36:45 pmMCO - MAF
2 stops6h 40mSouthwest
Deal found 12/16$724
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:00 amMAF - MCO
1 stop4h 44mUnited Airlines
Sun 1/119:10 amMCO - MAF
2 stops13h 44mUnited Airlines
Deal found 12/16$815
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:06 pmMAF - MCO
1 stop9h 37mUnited Airlines
Sun 1/47:00 pmMCO - MAF
1 stop5h 25mUnited Airlines
Deal found 12/16$1,107
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/316:00 amMAF - MCO
2 stops8h 27mAmerican Airlines
Sun 1/47:08 amMCO - MAF
1 stop11h 26mAmerican Airlines
Deal found 12/16$1,120

Find flight deals from Midland to Kissimmee

Keep the following information in mind while searching for Midland to Kissimmee flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$321
(American Airlines)

Popular in

May

Cheapest in

August

Average price

$461
Provider with most accurate pricing for Midland Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Midland Intl-Orlando (ORL) flights.
Search Deals
From Midland Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midland 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 December 18, 2025.
Use the filters below to find and compare flights from Midland to Kissimmee that are best for you.

Fly from

Midland

Fly to

Kissimmee

Route

Depart

Return

Price

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Mon 2/23

2:23 pm-9:22 pm

1 stop5h 59m

Orlando

Fri 2/27

7:23 pm-11:59 pm

1 stop5h 36m

$321

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Tue 2/24

5:00 am-11:52 am

1 stop5h 52m

Orlando

Wed 2/25

6:59 pm-11:15 pm

1 stop5h 16m

$341

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Tue 1/20

12:00 pm-5:54 pm

1 stop4h 54m

Orlando

Wed 1/21

3:30 pm-7:49 pm

1 stop5h 19m

$341

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 1/9

5:35 pm-11:14 pm

1 stop4h 39m

Orlando

Tue 1/13

9:00 am-4:21 pm

1 stop8h 21m

$364

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 3/6

6:40 pm-12:20 am

1 stop4h 40m

Orlando

Tue 3/10

4:10 pm-10:55 pm

1 stop7h 45m

$374

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Mon 2/23

7:40 am-4:20 pm

2 stops7h 40m

Orlando

Fri 2/27

4:50 pm-11:50 pm

2 stops8h 00m

$390

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 1/2

5:00 am-10:44 am

1 stop4h 44m

Orlando

Tue 1/6

11:47 am-4:21 pm

1 stop5h 34m

$547

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Best time to book a flight from Midland to Kissimmee

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

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

Currently, July is the cheapest month in which you can book a flight from Midland to Kissimmee (average of $213). Flying from Midland to Kissimmee in January is currently the most expensive (average of $371). 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 December 18, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Midland to Kissimmee. 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.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Crew

8.6

Overall

7.9

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Midland to Kissimmee. 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 from for flights from Midland to Kissimmee?

    Midland Intl (MAF), located 8.2 mi from the city center, is the airport you fly out of when you book flights from Midland to Kissimmee. 4 airlines have flights from Midland Intl to Kissimmee on a regular basis. Booking flights from Midland Intl to Kissimmee should not be difficult; the airport handles an average of 0 outbound flights to Kissimmee per day.

  • How long is the flight from Midland to Kissimmee?

    American Airlines, United Airlines, and Southwest can get you from Midland to Kissimmee in just under 4h 40m. Your travel time can differ by up to 1h 19m. Midland and Kissimmee are separated by a distance of 1268 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Midland to Kissimmee for a low price.

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

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

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

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

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

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

    Currently, July is the cheapest month in which you can book a flight from Midland to Kissimmee (average of $213). Flying from Midland to Kissimmee in January is currently the most expensive (average of $371). 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

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Top 4 airlines flying from Midland to Kissimmee

Discover the top 4 airlines that operate flights from Midland 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$413FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$216Average$361FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$216Average$410FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$300FlexibilityNo cancel feeOn-timeN/A

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