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Midland

$161+ Cheap flights from Kissimmee, FL to Midland (MAF)

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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — MAF
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Kissimmee to Midland

Cheapest flights from Kissimmee to Midland
Explore the most affordable flight options available from Kissimmee to Midland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This Southwest deal was found by Cheapflights users on 2/3. 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 3/97:35 am
MCO
-
MAF
1 stop7h 15m
Southwest
Thu 3/123:30 pm
MAF
-
MCO
1 stop7h 40m
Southwest
Deal found 2/3$321
This American Airlines deal was found by Cheapflights users on 2/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/108:00 am
MCO
-
MAF
1 stop10h 48m
American Airlines
Sat 10/172:35 pm
MAF
-
MCO
1 stop8h 32m
American Airlines
Deal found 2/2$329
This Southwest deal was found by Cheapflights users on 2/3. 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 4/137:55 am
MCO
-
MAF
1 stop8h 05m
Southwest
Thu 4/163:50 pm
MAF
-
MCO
1 stop4h 40m
Southwest
Deal found 2/3$366
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Sat 10/1011:20 am
MCO
-
MAF
2 stops11h 43m
United Airlines
Sat 10/1712:08 pm
MAF
-
MCO
1 stop4h 41m
United Airlines
Deal found 2/2$406
This American Airlines deal was found by Cheapflights users on 2/3. 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 8/97:30 am
MCO
-
MAF
1 stop5h 13m
American Airlines
Sat 8/152:30 pm
MAF
-
MCO
1 stop6h 30m
American Airlines
Deal found 2/3$440
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/117:00 am
MCO
-
MAF
1 stop14h 49m
American Airlines
Tue 2/249:18 am
MAF
-
MCO
1 stop6h 58m
American Airlines
Deal found 2/3$534

Find flight deals from Kissimmee to Midland

Keep the following information in mind while searching for Kissimmee to Midland flight deals. Data was last updated February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$321
(Southwest)

One-way from

$161
(United Airlines)

Popular in

April

Cheapest in

August

Average price

$614
Provider with most accurate pricing for Orlando (ORL)-Midland Intl flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Midland Intl flights.
Search Deals
From Kissimmee to Midland Intl
Search Deals
One-way flight from Kissimmee to Midland Intl
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Midland 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 4, 2026.
Use the filters below to find and compare flights from Kissimmee to Midland that are best for you.

Fly from

Kissimmee

Fly to

Midland

Route

Depart

Return

Price

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Mon 3/9

7:35 am-1:50 pm

1 stop7h 15m

Midland Intl

Thu 3/12

3:30 pm-12:10 am

1 stop7h 40m

$321

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Mon 4/13

7:55 am-3:00 pm

1 stop8h 05m

Midland Intl

Thu 4/16

3:50 pm-9:30 pm

1 stop4h 40m

$366

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Sat 2/14

6:15 pm-1:48 pm

2 stops20h 33m

Midland Intl

Wed 2/18

5:00 am-10:42 am

1 stop4h 42m

$720

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Fri 5/15

8:00 am-4:26 pm

1 stop9h 26m

$161

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Thu 2/12

6:04 pm-10:49 pm

1 stop5h 45m

$419

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Mon 2/9

6:29 pm-10:54 pm

1 stop5h 25m

$519

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Mon 2/9

11:35 am-6:15 pm

2 stops7h 40m

$524

OrlandoMidland

MCO - MAF

MCOMAF

Orlando

Fri 5/15

7:15 am-9:42 am

3 stops27h 27m

$560

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Best time to book a flight from Kissimmee to Midland

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

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

Currently, August is the cheapest month in which you can book a flight from Kissimmee to Midland (average of $94). Flying from Kissimmee to Midland in April is currently the most expensive (average of $935). 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 Midland

Get insights into the airlines that provide service to Midland. 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 Midland. Reviews last updated February 4, 2026.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Kissimmee to Midland have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,216 reviews
Southwest
8.0
Very good
4,272 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

    Located just 8.2 mi from the city center, Midland Intl is the airport most travelers will use when flying to Midland from Kissimmee. Booking flights from Kissimmee to Midland Intl (MAF) should be relatively easy as there are 0 daily inbound flights from Kissimmee from 3 different airlines.

  • How long is the flight from Kissimmee to Midland?

    Southwest can get you from Kissimmee to Midland in just under 7h 15m. Your travel time can differ by up to . Kissimmee and Midland are separated by a distance of 1268 mi.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Kissimmee to Midland (average of $94). Flying from Kissimmee to Midland in April is currently the most expensive (average of $935). 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 Midland?

Book flights to Midland if you plan to visit one of these locations
Fort Stockton
Barstow

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Alternative routes for Kissimmee to Midland

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Top 3 airlines flying from Kissimmee to Midland

Discover the top 3 airlines that operate flights from Kissimmee to Midland. 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 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$94Average$387FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$133Average$446FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$260Average$434FlexibilityNo cancel feeOn-time69%

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