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Kissimmee

$208+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MCO
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Midland Intl to Kissimmee are usually found in September or July, booked 76 days in advance, depart on a Thursday or Monday and return on a Thursday

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 July 31, 2025.

Round-trip from

$217
(American Airlines)

One-way from

$208
(American Airlines)

Popular in

October

Cheapest in

September

Average price

$303
From Midland Intl to Kissimmee
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One-way flight from Midland Intl to Kissimmee
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/29. 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 9/712:35 pmMAF - MCO
1 stop7h 52mAmerican Airlines
Sat 9/138:29 amMCO - MAF
1 stop8h 13mAmerican Airlines
Deal found 7/29$217
This Southwest deal was found by Cheapflights users on 7/29. 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 8/227:40 amMAF - MCO
2 stops10h 00mSouthwest
Fri 8/296:50 amMCO - MAF
1 stop9h 35mSouthwest
Deal found 7/29$222
This United Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 8/255:00 amMAF - MCO
2 stops8h 57mUnited Airlines
Thu 8/2812:00 pmMCO - MAF
1 stop5h 12mUnited Airlines
Deal found 7/31$272
This Delta deal was found by Cheapflights users on 7/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/245:30 amMAF - MCO
1 stop5h 20mDelta
Sun 9/286:00 amMCO - MAF
2 stops6h 53mDelta
Deal found 7/29$321

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 July 31, 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

Sun 9/7

12:35 pm-9:27 pm

1 stop7h 52m

Orlando

Sat 9/13

6:30 am-10:47 am

1 stop5h 17m

$217

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 8/22

7:40 am-6:40 pm

2 stops10h 00m

Orlando

Fri 8/29

6:50 am-3:25 pm

1 stop9h 35m

$222

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Mon 8/25

5:00 am-2:57 pm

2 stops8h 57m

Orlando

Thu 8/28

12:00 pm-4:12 pm

1 stop5h 12m

$272

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Wed 9/24

5:30 am-11:50 am

1 stop5h 20m

Orlando

Sun 9/28

6:00 am-11:53 am

2 stops6h 53m

$321

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Thu 8/14

7:36 am-3:10 pm

1 stop6h 34m

$208

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Thu 8/14

5:30 am-1:24 pm

2 stops6h 54m

$213

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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

How far ahead should I book a flight from Midland to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Midland to Kissimmee. Price data was last updated on July 25, 2025.

The best time to book flights from Midland to Kissimmee is 34 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, May is the cheapest month in which you can book a flight from Midland to Kissimmee (average of $206). Flying from Midland to Kissimmee in November is currently the most expensive (average of $288). 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 July 31, 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
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

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.

  • 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, May is the cheapest month in which you can book a flight from Midland to Kissimmee (average of $206). Flying from Midland to Kissimmee in November is currently the most expensive (average of $288). 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$213Average$388FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$303FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$216Average$514FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$216Average$418FlexibilityNo cancel feeOn-time71%

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