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Kissimmee

$69+ 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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MCO
Sep 2 — Sep 91
Tue 9/2
Tue 9/9
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Kissimmee are usually found in September or August, booked 72 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Madison to Kissimmee

Keep the following information in mind while searching for Madison to Kissimmee flight deals. Data was last updated August 28, 2025.

Round-trip from

$158
(Breeze Airways)

One-way from

$69
(Breeze Airways)

Popular in

March

Cheapest in

September

Average price

$281
From Madison Truax Field to Kissimmee
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One-way flight from Madison Truax Field to Kissimmee
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Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 28, 2025.

This Breeze Airways deal was found by Cheapflights users on 8/25. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Wed 10/83:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/25$158
This Priceline deal was found by Cheapflights users on 8/28. 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 10/186:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Wed 10/223:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/28$173
This Priceline deal was found by Cheapflights users on 8/27. 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.
Wed 9/106:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Sat 9/133:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/27$176
This Breeze Airways deal was found by Cheapflights users on 8/26. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Sat 11/83:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/26$178
This Priceline deal was found by Cheapflights users on 8/26. 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 10/256:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Wed 10/293:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/26$183
This Breeze Airways deal was found by Cheapflights users on 8/27. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Sat 11/153:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/27$188
This Breeze Airways deal was found by Cheapflights users on 8/26. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/3010:19 amMSN - MCO
Nonstop2h 50mBreeze Airways
Wed 9/103:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 8/26$218
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/224:51 pmMSN - MCO
1 stop6h 33mAmerican Airlines
Thu 11/276:01 amMCO - MSN
1 stop5h 14mAmerican Airlines
Deal found 8/28$225
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:40 pmMSN - MCO
1 stop7h 27mAmerican Airlines
Tue 12/306:00 amMCO - MSN
1 stop5h 05mAmerican Airlines
Deal found 8/28$229
This Expedia deal was found by Cheapflights users on 8/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/106:08 pmMSN - MCO
Nonstop3h 00mMultiple Airlines
Fri 9/126:00 amMCO - MSN
1 stop14h 14mMultiple Airlines
Deal found 8/28$233

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 August 28, 2025.
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

Sat 10/4

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Wed 10/8

3:09 pm-5:28 pm

Nonstop3h 19m

$158

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 10/18

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Wed 10/22

3:09 pm-5:28 pm

Nonstop3h 19m

$173

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 9/10

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Sat 9/13

3:09 pm-5:28 pm

Nonstop3h 19m

$176

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 11/1

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Sat 11/8

3:09 pm-5:28 pm

Nonstop3h 19m

$178

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 11/12

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Sat 11/15

3:09 pm-5:28 pm

Nonstop3h 19m

$178

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 10/25

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Wed 10/29

3:09 pm-5:28 pm

Nonstop3h 19m

$183

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 11/12

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Wed 11/19

3:09 pm-5:28 pm

Nonstop3h 19m

$188

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 11/19

6:08 pm-10:08 pm

Nonstop3h 00m

Orlando

Wed 11/26

3:09 pm-5:28 pm

Nonstop3h 19m

$218

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 9/27

6:08 pm-10:08 pm

Nonstop3h 00m

$69

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 11/8

6:08 pm-10:08 pm

Nonstop3h 00m

$71

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/26

Showing 1-10 of 18 results
1
2

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 August 22, 2025.

Booking 72 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 $206). Flying from Madison 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.

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 August 28, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Kissimmee as you normally would.

What is the cheapest day to fly from Madison to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Madison to Kissimmee. Price data was last updated on August 24, 2025.

Travelers seeking maximum savings on their Madison to Kissimmee flight should consider departing on Wednesday mornings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 August 28, 2025.
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
8.0
Very good
199 reviews

Food

6.7

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.1

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
199 reviews
Breeze Airways
8.0
Very good
199 reviews

Food

6.7

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.1

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Delta
8.0
Very good
7,977 reviews
Breeze Airways
8.0
Very good
199 reviews

Food

6.7

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.1

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
United Airlines
7.4
Good
8,944 reviews
Breeze Airways
8.0
Very good
199 reviews

Food

6.7

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.1

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.0
Very good
199 reviews

Food

6.7

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.1

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Frontier
5.8
Fair
3,204 reviews
Breeze Airways
8.0
Very good
199 reviews

Food

6.7

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.6

Comfort

8.1

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 3h. Breeze Airways provides one of the quickest options available for as low as $158. The distance between Madison and Kissimmee is about 1109 mi. Generally, flights for this route are nonstop.

  • What are the cheapest flights from Madison to Kissimmee?

    While on average a flight from Madison to Kissimmee is generally $200, 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 $138 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 $206). Flying from Madison 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 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 August 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$116Average$208FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$158Average$315FlexibilityNo cancel feeOn-time62%
DeltaCheapest$193Average$352FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$198Average$408FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$208Average$405FlexibilityNo cancel feeOn-time71%

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