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Kissimmee

$181+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
MAF — MCO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$222
(Delta)

Popular in

October

Cheapest in

August

Average price

$483
From Midland Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 16, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 10/245:11 pmMAF - MCO
2 stops11h 44mDelta
Mon 10/2712:42 pmMCO - MAF
1 stop4h 49mDelta
Deal found 9/15$222
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/312:31 pmMAF - MCO
1 stop5h 22mAmerican Airlines
Fri 11/75:15 amMCO - MAF
1 stop5h 30mAmerican Airlines
Deal found 9/16$240
This Southwest deal was found by Cheapflights users on 9/15. 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 10/315:45 amMAF - MCO
1 stop5h 55mSouthwest
Mon 11/35:15 pmMCO - MAF
1 stop5h 55mSouthwest
Deal found 9/15$258
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/292:25 pmMAF - MCO
1 stop4h 44mAmerican Airlines
Wed 11/51:30 pmMCO - MAF
1 stop5h 51mAmerican Airlines
Deal found 9/14$299
This Southwest deal was found by Cheapflights users on 9/15. 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 10/244:45 pmMAF - MCO
1 stop5h 30mSouthwest
Mon 10/279:20 amMCO - MAF
1 stop7h 45mSouthwest
Deal found 9/15$318
This Southwest deal was found by Cheapflights users on 9/14. 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 10/310:00 amMAF - MCO
1 stop7h 55mSouthwest
Mon 10/65:05 pmMCO - MAF
1 stop6h 50mSouthwest
Deal found 9/14$326

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 September 16, 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

Fri 10/24

5:11 pm-5:55 am

2 stops11h 44m

Orlando

Mon 10/27

12:42 pm-4:31 pm

1 stop4h 49m

$222

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 10/31

2:31 pm-8:53 pm

1 stop5h 22m

Orlando

Fri 11/7

5:15 am-9:45 am

1 stop5h 30m

$240

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 10/31

5:45 am-12:40 pm

1 stop5h 55m

Orlando

Mon 11/3

5:15 pm-10:10 pm

1 stop5h 55m

$258

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 10/24

4:45 pm-11:15 pm

1 stop5h 30m

Orlando

Mon 10/27

9:20 am-4:05 pm

1 stop7h 45m

$318

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Fri 10/3

10:00 am-6:55 pm

1 stop7h 55m

Orlando

Mon 10/6

5:05 pm-10:55 pm

1 stop6h 50m

$326

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Wed 10/29

1:55 pm-12:55 am

2 stops10h 00m

Orlando

Wed 11/5

5:10 pm-11:15 pm

1 stop7h 05m

$349

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sat 3/7

4:20 pm-10:10 pm

1 stop4h 50m

$181

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sun 3/8

6:45 pm-12:15 am

1 stop4h 30m

$254

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sun 3/8

5:00 am-5:47 pm

3 stops11h 47m

$460

MidlandOrlando

MAF - MCO

MAFMCO

Midland Intl

Sat 3/7

5:00 am-5:47 pm

3 stops11h 47m

$1,100

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, 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 $289). 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 September 16, 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
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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
4,242 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

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?

    Delta, American Airlines, and Southwest can get you from Midland to Kissimmee in just under 5h 22m. Your travel time can differ by up to 6h 22m. Midland and Kissimmee are separated by a distance of 1268 mi. This flight may include one or multiple stops.

  • 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 $289). 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$213Average$378FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$216Average$509FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$216Average$422FlexibilityNo cancel feeOn-time71%
DeltaCheapest$216Average$303FlexibilityNo cancel feeOn-timeN/A

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