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Kissimmee

$131+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MCO
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This Southwest deal was found by Cheapflights users on 2/1. 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.
Tue 3/36:40 am
MAF
-
MCO
1 stop4h 40m
Southwest
Tue 3/108:30 am
MCO
-
MAF
1 stop6h 45m
Southwest
Deal found 2/1$291
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 3/96:40 pm
MAF
-
MCO
1 stop4h 40m
Southwest
Wed 3/116:25 am
MCO
-
MAF
1 stop6h 25m
Southwest
Deal found 2/3$321
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:00 am
MAF
-
MCO
2 stops6h 50m
Southwest
Wed 5/136:30 am
MCO
-
MAF
1 stop4h 55m
Southwest
Deal found 2/2$341
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.
Thu 3/53:20 pm
MAF
-
MCO
1 stop14h 45m
Southwest
Sun 3/86:20 am
MCO
-
MAF
1 stop6h 25m
Southwest
Deal found 2/3$344
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sun 5/173:45 pm
MAF
-
MCO
1 stop5h 00m
Southwest
Sat 5/236:30 am
MCO
-
MAF
1 stop6h 05m
Southwest
Deal found 2/1$374
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.
Tue 3/31:50 pm
MAF
-
MCO
1 stop8h 40m
United Airlines
Tue 3/1011:52 am
MCO
-
MAF
2 stops11h 23m
United Airlines
Deal found 2/2$376
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.
Tue 3/312:22 pm
MAF
-
MCO
1 stop5h 56m
American Airlines
Tue 3/106:08 pm
MCO
-
MAF
1 stop5h 41m
American Airlines
Deal found 2/2$397
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.
Sun 5/32:13 pm
MAF
-
MCO
1 stop4h 59m
United Airlines
Wed 5/67:01 pm
MCO
-
MAF
1 stop5h 14m
United Airlines
Deal found 2/2$401

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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$291
(Southwest)

One-way from

$131
(United Airlines)

Popular in

May

Cheapest in

August

Average price

$388
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
One-way flight from Midland Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($134 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 February 2026
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 February 3, 2026.
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

Tue 3/3

6:40 am-12:20 pm

1 stop4h 40m

Orlando

Tue 3/10

8:30 am-2:15 pm

1 stop6h 45m

$291

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Wed 5/6

7:00 am-1:42 pm

1 stop5h 42m

Orlando

Wed 5/13

9:42 am-4:31 pm

1 stop7h 49m

$321

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Wed 5/6

11:00 am-6:50 pm

2 stops6h 50m

Orlando

Wed 5/13

6:30 am-10:25 am

1 stop4h 55m

$341

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Thu 3/5

3:20 pm-7:05 am

1 stop14h 45m

Orlando

Sun 3/8

6:20 am-11:45 am

1 stop6h 25m

$344

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sun 5/17

3:45 pm-9:45 pm

1 stop5h 00m

Orlando

Sat 5/23

6:30 am-11:35 am

1 stop6h 05m

$374

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Tue 3/3

1:50 pm-11:30 pm

1 stop8h 40m

Orlando

Tue 3/10

11:52 am-10:15 pm

2 stops11h 23m

$376

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sun 5/3

2:13 pm-8:12 pm

1 stop4h 59m

Orlando

Wed 5/6

7:01 pm-11:15 pm

1 stop5h 14m

$401

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Tue 3/3

5:00 am-1:27 pm

1 stop7h 27m

$131

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Tue 3/3

11:05 am-6:40 pm

2 stops6h 35m

$136

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sat 4/4

2:30 pm-10:25 pm

1 stop6h 55m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 15 results
1
2

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 $212). Flying from Midland to Kissimmee in March is currently the most expensive (average of $285). 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 3, 2026.
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
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

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
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

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
8,138 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

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
9,236 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

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
11,216 reviews
Southwest
8.0
Very good
4,272 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

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?

    Southwest and United Airlines can get you from Midland to Kissimmee in just under 4h 40m. Your travel time can differ by up to 1h 02m. 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 $212). Flying from Midland to Kissimmee in March is currently the most expensive (average of $285). 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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Alternative routes for Midland to Kissimmee

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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$216Average$393FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$216Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$216Average$354FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$300FlexibilityNo cancel feeOn-timeN/A

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