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Kissimmee

$234+ Cheap flights from Midland (MAF) 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MCO
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find 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 November 3, 2025.

This Southwest deal was found by Cheapflights users on 11/1. 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.
Mon 12/223:45 pmMAF - MCO
1 stop7h 10mSouthwest
Wed 1/76:05 amMCO - MAF
1 stop5h 15mSouthwest
Deal found 11/1$320
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 11/203:35 pmMAF - MCO
1 stop5h 35mSouthwest
Tue 12/25:15 pmMCO - MAF
1 stop5h 55mSouthwest
Deal found 11/2$404
This American Airlines deal was found by Cheapflights users on 11/1. 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 12/32:34 pmMAF - MCO
1 stop5h 45mAmerican Airlines
Wed 12/105:13 amMCO - MAF
1 stop7h 39mAmerican Airlines
Deal found 11/1$431
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 11/255:00 amMAF - MCO
1 stop4h 45mUnited Airlines
Wed 12/35:05 pmMCO - MAF
1 stop5h 54mUnited Airlines
Deal found 11/2$444
This United Airlines deal was found by Cheapflights users on 11/2. 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 12/35:00 amMAF - MCO
1 stop15h 59mUnited Airlines
Wed 12/108:00 amMCO - MAF
1 stop9h 39mUnited Airlines
Deal found 11/2$463
This United Airlines deal was found by Cheapflights users on 11/2. 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 11/265:00 amMAF - MCO
1 stop4h 45mUnited Airlines
Wed 12/33:35 pmMCO - MAF
1 stop7h 24mUnited Airlines
Deal found 11/2$510

Cheap flight deals from Midland to Kissimmee

Keep the following information in mind while searching for Midland to Kissimmee flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$263
(Southwest)

One-way from

$234
(United Airlines)

Popular in

January

Cheapest in

August

Average price

$435
Provider with most accurate pricing for Midland Intl-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Midland Intl-Orlando (ORL) flights.
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From Midland Intl to Kissimmee
Search Deals
One-way flight from Midland Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 3, 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 1/12

4:20 pm-9:55 pm

1 stop4h 35m

Orlando

Thu 1/15

5:05 pm-10:15 pm

1 stop6h 10m

$263

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Mon 12/22

6:15 pm-11:55 pm

1 stop4h 40m

Orlando

Wed 1/7

6:10 am-11:00 am

1 stop5h 50m

$320

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Wed 1/14

7:00 am-3:46 pm

1 stop7h 46m

Orlando

Tue 1/20

11:47 am-4:21 pm

1 stop5h 34m

$341

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Tue 3/3

7:00 am-3:42 pm

1 stop7h 42m

Orlando

Wed 3/4

8:14 am-4:33 pm

1 stop9h 19m

$341

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Thu 11/20

3:35 pm-10:10 pm

1 stop5h 35m

Orlando

Tue 12/2

5:15 pm-10:10 pm

1 stop5h 55m

$404

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Wed 12/3

2:34 pm-9:19 pm

1 stop5h 45m

Orlando

Wed 12/10

5:13 am-11:52 am

1 stop7h 39m

$431

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sun 11/23

3:05 pm-9:58 pm

1 stop5h 53m

$234

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sun 11/23

3:25 pm-10:40 pm

2 stops6h 15m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

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 $342). 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.

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?

    Southwest can get you from Midland to Kissimmee in just under 4h 35m. Your travel time can differ by up to . Midland and Kissimmee are separated by a distance of 1268 mi.

  • 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 $342). 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$428FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$216Average$442FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$276FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$296Average$386FlexibilityNo cancel feeOn-time69%

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