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Kissimmee

$68+ Cheap flights from Madison (MSN) 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MCO
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Kissimmee are usually found in August or January, booked 23 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

Cheap flight deals from Madison to Kissimmee

Cheapest flights from Madison to Kissimmee
Explore the most affordable flight options available from Madison to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:55 pm
MSN
-
MCO
Nonstop2h 49m
Breeze Airways
Sat 9/55:07 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 7/26$137
This Kiwi.com deal was found by Cheapflights users on 7/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 pm
MSN
-
MCO
Nonstop3h 00m
Breeze Airways
Tue 9/221:40 pm
MCO
-
MSN
Nonstop3h 20m
Breeze Airways
Deal found 7/22$138
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:55 pm
MSN
-
MCO
Nonstop2h 49m
Breeze Airways
Wed 9/23:17 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 7/27$147
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 pm
MSN
-
MCO
Nonstop3h 00m
Breeze Airways
Sun 9/203:00 pm
MCO
-
MSN
Nonstop3h 20m
Breeze Airways
Deal found 7/23$168
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:55 pm
MSN
-
MCO
Nonstop2h 49m
Breeze Airways
Wed 8/263:17 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 7/23$178
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:55 pm
MSN
-
MCO
Nonstop2h 49m
Breeze Airways
Wed 8/193:17 pm
MCO
-
MSN
Nonstop3h 08m
Breeze Airways
Deal found 7/25$183
This Priceline deal was found by Cheapflights users on 7/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:54 pm
MSN
-
MCO
1 stop8h 42m
Multiple Airlines
Tue 10/207:30 am
MCO
-
MSN
Nonstop3h 20m
Multiple Airlines
Deal found 7/26$191
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:55 pm
MSN
-
MCO
Nonstop2h 49m
Multiple Airlines
Tue 9/15:23 pm
MCO
-
MSN
2 stops17h 24m
Multiple Airlines
Deal found 7/23$192

Find flight deals from Madison to Kissimmee

Keep the following information in mind while searching for Madison to Kissimmee flight deals. Data was last updated July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

July

Cheapest in

August

Average price

$443
Provider with most accurate pricing for Madison Truax Field-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Orlando (ORL) flights.
Search Deals
From Madison Truax Field to Kissimmee
Search Deals
One-way flight from Madison Truax Field to Kissimmee
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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 27, 2026.
Use the filters below to find and compare flights from Madison to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 10/21

1:29 pm-7:21 pm

1 stop4h 52m

Orlando

Wed 10/28

6:35 am-10:33 am

1 stop4h 58m

$295

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Tue 10/6

5:10 am-1:58 pm

1 stop7h 48m

Orlando

Sat 10/10

6:00 pm-10:35 pm

1 stop5h 35m

$385

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 10/21

6:49 am-5:04 pm

2 stops9h 15m

Orlando

Wed 10/28

10:54 am-3:00 pm

1 stop5h 06m

$390

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 9/12

2:44 pm-10:03 pm

1 stop6h 19m

Orlando

Wed 9/16

12:00 pm-8:53 pm

2 stops9h 53m

$390

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 10/7

8:10 am-6:15 pm

2 stops9h 05m

Orlando

Sat 10/10

7:15 am-1:37 pm

1 stop7h 22m

$390

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 10/17

5:00 am-6:15 pm

2 stops12h 15m

Orlando

Sat 10/24

7:22 am-3:04 pm

2 stops8h 42m

$395

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 10/7

6:49 am-6:15 pm

2 stops10h 26m

Orlando

Tue 10/13

12:33 pm-9:00 pm

2 stops9h 27m

$395

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 8/1

2:45 pm-11:58 pm

1 stop8h 13m

Orlando

Tue 8/4

11:05 am-4:20 pm

1 stop6h 15m

$401

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 10/23

2:49 pm-11:53 pm

1 stop8h 04m

Orlando

Tue 10/27

11:06 am-7:02 pm

2 stops8h 56m

$407

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 9/26

4:10 pm-12:59 am

2 stops7h 49m

Orlando

Mon 9/28

12:33 pm-10:35 pm

2 stops11h 02m

$412

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Best time to book a flight from Madison to Kissimmee

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

What is the cheapest time of day to fly from MSN to K1S?

Find hourly flight availability from Madison to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

When flying from Madison to Kissimmee, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 48% versus a flight at noon.

How much does it cost to fly round-trip from Madison to Kissimmee?

Airfare is below average for this route at the moment.
Madison to Kissimmee flights typically cost between $279 and $344 in August.
The cheapest round-trip price found within the last 5 days was $137 on Breeze Airways (Aug 29-Sep 5).

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 27, 2026.
Read reviews from past customers who have flown Breeze Airways,Delta, andUnited Airlines from Madison 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.
Breeze Airways
8.2
Very good
301 reviews

Overall

8.2

Comfort

8.2

Entertainment

6.7

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Breeze Airways
8.2
Very good
301 reviews
Breeze Airways
8.2
Very good
301 reviews

Overall

8.2

Comfort

8.2

Entertainment

6.7

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Delta
7.8
Good
8,483 reviews
Breeze Airways
8.2
Very good
301 reviews

Overall

8.2

Comfort

8.2

Entertainment

6.7

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
United Airlines
7.4
Good
10,042 reviews
Breeze Airways
8.2
Very good
301 reviews

Overall

8.2

Comfort

8.2

Entertainment

6.7

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
American Airlines
7.1
Good
11,842 reviews
Breeze Airways
8.2
Very good
301 reviews

Overall

8.2

Comfort

8.2

Entertainment

6.7

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.
Frontier
5.6
Fair
2,755 reviews
Breeze Airways
8.2
Very good
301 reviews

Overall

8.2

Comfort

8.2

Entertainment

6.7

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 18
4.0
Okay

Lisa,Mar 2026

ORF - JAX

*Flight was delayed twice *Once plane arrived crew closed the entryway to discuss whatever, leaving us to wait again. *Finally arriving Jax, we were delayed again for 20 minutes because another plane at the gate hadn’t pushed back Overall, score 2 out of 5. Lots of passengers upset.

Related info for your journey

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

    Madison Truax Field (MSN), located 5.4 mi from the city center, is the airport you fly out of when you book flights from Madison to Kissimmee. 5 airlines have flights from Truax Field to Kissimmee on a regular basis. Booking flights from Madison Truax Field 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 Madison to Kissimmee?

    A quick flight from Madison to Kissimmee can take about 4h 52m. Delta provides one of the quickest options available for as low as $295. The distance between Madison and Kissimmee is about 1109 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Madison to Kissimmee one-way?

    The cheapest airlines for a one-way flight from Madison to Kissimmee are Breeze Airways ($69), Frontier ($84), and American Airlines ($125).

  • What are the cheapest flights from Madison to Kissimmee?

    While on average a flight from Madison to Kissimmee is generally $166, our data shows the cheapest flight currently is $79. When looking at the most popular route, (Madison Truax Field - Orlando), you can expect to pay $137 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison 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.

See more FAQs

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Alternative routes for Madison to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Madison to Kissimmee

Discover the top 5 airlines that operate flights from Madison 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$138Average$250FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$149Average$317FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$224Average$462FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$251Average$378FlexibilityNo cancel feeOn-time69%

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