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Kissimmee

$88+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Kissimmee are usually found in August or September, booked 51 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

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 January 29, 2026.

This Priceline deal was found by Cheapflights users on 1/28. 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 2/286:36 pm
MSN
-
MCO
Nonstop3h 04m
Multiple Airlines
Sat 3/73:50 pm
MCO
-
MSN
Nonstop3h 15m
Multiple Airlines
Deal found 1/28$233
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 3/116:36 pm
MSN
-
MCO
Nonstop3h 04m
Breeze Airways
Tue 3/173:00 pm
MCO
-
MSN
Nonstop3h 21m
Breeze Airways
Deal found 1/27$236
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:56 pm
MSN
-
MCO
1 stop8h 37m
Frontier
Thu 3/2611:02 am
MCO
-
MSN
Nonstop3h 19m
Frontier
Deal found 1/26$243
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:29 pm
MSN
-
MCO
Nonstop2h 59m
Frontier
Sat 3/143:12 pm
MCO
-
MSN
Nonstop3h 15m
Frontier
Deal found 1/27$244
This Mytrip deal was found by Cheapflights users on 1/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:36 pm
MSN
-
MCO
Nonstop3h 04m
Breeze Airways
Sat 5/23:35 pm
MCO
-
MSN
Nonstop3h 21m
Breeze Airways
Deal found 1/28$245
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 1/316:16 pm
MSN
-
MCO
Nonstop3h 04m
Breeze Airways
Wed 2/113:35 pm
MCO
-
MSN
Nonstop3h 21m
Breeze Airways
Deal found 1/27$246
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 1/316:16 pm
MSN
-
MCO
Nonstop3h 04m
Multiple Airlines
Tue 2/103:07 pm
MCO
-
MSN
2 stops19h 01m
Multiple Airlines
Deal found 1/27$247
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:30 am
MSN
-
MCO
1 stop5h 10m
United Airlines
Tue 3/32:00 pm
MCO
-
MSN
1 stop8h 07m
United Airlines
Deal found 1/27$251
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:14 pm
MSN
-
MCO
Nonstop3h 00m
Multiple Airlines
Wed 3/183:35 pm
MCO
-
MSN
Nonstop3h 21m
Multiple Airlines
Deal found 1/27$252
This Priceline deal was found by Cheapflights users on 1/28. 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.
Wed 3/46:36 pm
MSN
-
MCO
Nonstop3h 04m
Multiple Airlines
Sat 3/73:50 pm
MCO
-
MSN
Nonstop3h 15m
Multiple Airlines
Deal found 1/28$255
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/213:53 pm
MSN
-
MCO
2 stops7h 50m
United Airlines
Tue 2/2410:58 am
MCO
-
MSN
1 stop4h 59m
United Airlines
Deal found 1/27$256
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/912:29 pm
MSN
-
MCO
Nonstop3h 00m
Frontier
Sat 3/143:12 pm
MCO
-
MSN
Nonstop3h 15m
Frontier
Deal found 1/28$259

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$233
(Priceline)

One-way from

$88
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$319
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. 5% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
Use the filters below to find and compare flights from Madison to Kissimmee that are best for you.

Fly from

Madison

Fly to

Kissimmee

Route

Depart

Return

Price

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 2/25

6:05 am-1:31 pm

1 stop6h 26m

Orlando

Wed 3/4

9:25 am-2:57 pm

1 stop6h 32m

$251

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 4/17

5:04 pm-1:08 am

1 stop7h 04m

Orlando

Sat 4/25

5:30 am-10:32 am

1 stop6h 02m

$279

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Thu 5/28

6:30 am-2:58 pm

1 stop7h 28m

Orlando

Tue 6/2

9:40 am-2:00 pm

1 stop5h 20m

$279

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Tue 3/24

3:54 pm-9:40 pm

1 stop4h 46m

Orlando

Tue 3/31

4:48 pm-9:16 pm

1 stop5h 28m

$279

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 4/18

3:53 pm-9:58 pm

1 stop5h 05m

Orlando

Sat 4/25

4:48 pm-9:16 pm

1 stop5h 28m

$279

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 4/25

3:53 pm-12:45 am

2 stops7h 52m

Orlando

Fri 5/1

9:02 am-3:00 pm

1 stop6h 58m

$284

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 5/9

8:15 am-2:41 pm

1 stop5h 26m

Orlando

Sat 5/16

12:12 pm-7:23 pm

2 stops8h 11m

$284

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 3/4

6:36 pm-10:40 pm

Nonstop3h 04m

Orlando

Wed 3/11

3:35 pm-5:56 pm

Nonstop3h 21m

$288

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 3/7

3:53 pm-12:33 am

2 stops7h 40m

Orlando

Wed 3/11

6:08 pm-10:42 pm

1 stop5h 34m

$296

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 2/21

2:48 pm-9:40 pm

1 stop5h 52m

Orlando

Wed 2/25

10:05 am-6:58 pm

2 stops9h 53m

$336

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 21 results
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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

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

Use this chart to determine the optimal time to book a round-trip flight from Madison to Kissimmee. Price data was last updated on January 23, 2026.

Booking 51 days in advance of your planned departure date is, on average, the best time to get cheap flights from Madison to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, May is the cheapest month in which you can book a flight from Madison to Kissimmee (average of $71). Flying from Madison to Kissimmee in March is currently the most expensive (average of $114). 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.

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 January 29, 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 51% versus a flight at noon.

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 January 29, 2026.
Read reviews from past customers who have flown Breeze Airways, Delta, and United 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
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Breeze Airways
8.2
Very good
263 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Delta
7.9
Good
8,127 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
United Airlines
7.4
Good
9,215 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
American Airlines
7.2
Good
11,206 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.
Frontier
5.7
Fair
3,056 reviews
Breeze Airways
8.2
Very good
263 reviews

Comfort

8.2

Crew

8.7

Boarding

8.3

Overall

8.2

Entertainment

6.6

Food

6.7

Reviews

1 / 17
2.0
Mediocre

Justine,Jan 2026

RDU - MCO

1/10, I have never experienced the amount of delays, my flight was supposed to board at 8:34pm, we didn’t board until 3:35am from RDU. The staff got rude and very disrespectful when you asked what was going on it was like we didn’t board until something wrong or were pestering them for answers. I was 1 question 1 time, they were not communicating with us at all. So when our plane was now 6+ hrs delayed and nothing was being said to us .. yeah I think we have a right to ask a question. Everything took so long and was such a process; I have never experienced this before and I’m a frequent flyer, breeze makes spirit airlines look like a 100/10 airline.

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 6h 26m. United Airlines provides one of the quickest options available for as low as $251. 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 ($79), and United Airlines ($99).

  • What are the cheapest flights from Madison to Kissimmee?

    While on average a flight from Madison to Kissimmee is generally $187, our data shows the cheapest flight currently is $71. When looking at the most popular route, (Madison Truax Field - Orlando), you can expect to pay $176 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.

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

    Currently, May is the cheapest month in which you can book a flight from Madison to Kissimmee (average of $71). Flying from Madison to Kissimmee in March is currently the most expensive (average of $114). 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 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$118Average$221FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$118Average$349FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$158Average$307FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$190Average$407FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$228Average$347FlexibilityNo cancel feeOn-time69%

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