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Kissimmee

$55+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MCO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 72 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 October 28, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
Fri 10/318:00 pmMSN - MCO
1 stop18h 38mFrontier
Mon 11/36:00 amMCO - MSN
1 stop14h 15mFrontier
Deal found 10/27$227
This Frontier deal was found by Cheapflights users on 10/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/148:00 pmMSN - MCO
1 stop8h 44mFrontier
Sun 11/166:00 amMCO - MSN
1 stop14h 15mFrontier
Deal found 10/26$228
This Gotogate deal was found by Cheapflights users on 10/27. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/86:08 pmMSN - MCO
Nonstop3h 00mMultiple Airlines
Wed 11/128:59 pmMCO - MSN
1 stop23h 16mMultiple Airlines
Deal found 10/27$230
This Priceline deal was found by Cheapflights users on 10/27. 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 11/196:08 pmMSN - MCO
Nonstop3h 00mMultiple Airlines
Wed 11/266:00 amMCO - MSN
1 stop10h 29mMultiple Airlines
Deal found 10/27$232
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:00 pmMSN - MCO
1 stop18h 05mFrontier
Sat 11/158:59 pmMCO - MSN
1 stop23h 16mFrontier
Deal found 10/27$238
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:08 pmMSN - MCO
Nonstop3h 00mBreeze Airways
Wed 11/263:09 pmMCO - MSN
Nonstop3h 19mBreeze Airways
Deal found 10/27$242
This Cheapflightsfares deal was found by Cheapflights users on 10/26. 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.
Thu 11/138:00 pmMSN - MCO
1 stop8h 44mFrontier
Mon 11/176:00 amMCO - MSN
1 stop14h 15mFrontier
Deal found 10/26$247
This Frontier deal was found by Cheapflights users on 10/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/27:59 pmMSN - MCO
1 stop8h 45mFrontier
Fri 11/76:00 amMCO - MSN
1 stop14h 15mFrontier
Deal found 10/26$248
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/78:00 pmMSN - MCO
1 stop8h 44mFrontier
Mon 11/246:00 amMCO - MSN
1 stop9h 25mFrontier
Deal found 10/27$249
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:32 pmMSN - MCO
1 stop5h 36mDelta
Wed 12/106:00 amMCO - MSN
1 stop7h 50mDelta
Deal found 10/28$251

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$228
(Frontier)

One-way from

$55
(Frontier)

Popular in

March

Cheapest in

August

Average price

$368
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. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 October 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 12/13

6:00 am-1:39 pm

1 stop6h 39m

Orlando

Wed 12/17

10:06 am-4:21 pm

1 stop7h 15m

$251

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 11/19

8:25 am-2:51 pm

1 stop5h 26m

Orlando

Wed 11/26

7:30 am-11:43 am

1 stop5h 13m

$255

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 12/17

5:14 pm-11:47 pm

1 stop5h 33m

Orlando

Mon 12/22

5:30 am-10:20 am

1 stop5h 50m

$255

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 12/12

6:00 am-1:39 pm

1 stop6h 39m

Orlando

Thu 12/18

6:40 am-12:42 pm

1 stop7h 02m

$259

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Fri 12/12

6:00 am-1:39 pm

1 stop6h 39m

Orlando

Mon 12/15

6:15 am-10:59 am

1 stop5h 44m

$259

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Mon 12/8

1:22 pm-9:12 pm

1 stop6h 50m

Orlando

Tue 12/9

5:35 pm-10:26 pm

1 stop5h 51m

$264

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 11/12

5:14 pm-10:49 pm

1 stop4h 35m

Orlando

Sat 11/15

9:00 am-12:32 pm

1 stop4h 32m

$277

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Thu 11/27

1:20 pm-8:44 pm

1 stop6h 24m

Orlando

Tue 12/2

8:15 am-12:50 pm

1 stop5h 35m

$285

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Thu 11/27

1:20 pm-8:44 pm

1 stop6h 24m

Orlando

Wed 12/3

10:06 am-4:21 pm

1 stop7h 15m

$285

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 11/12

6:08 pm-10:08 pm

Nonstop3h 00m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 19 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 October 24, 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 $71). Flying from Madison to Kissimmee in February is currently the most expensive (average of $118). 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 October 28, 2025.

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 43% versus a flight in the evening.

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 October 26, 2025.

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

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

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 October 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
8.1
Very good
220 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.1

Food

6.7

Entertainment

6.6

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
8.1
Very good
220 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.1

Food

6.7

Entertainment

6.6

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
7.9
Good
7,995 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.1

Food

6.7

Entertainment

6.6

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
8,996 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.1

Food

6.7

Entertainment

6.6

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
11,033 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.1

Food

6.7

Entertainment

6.6

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
3,122 reviews
Breeze Airways
8.1
Very good
220 reviews

Boarding

8.3

Crew

8.7

Overall

8.1

Comfort

8.1

Food

6.7

Entertainment

6.6

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 5h 26m. Delta provides one of the quickest options available for as low as $255. 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 ($109), Frontier ($114), and Delta ($126).

  • What are the cheapest flights from Madison to Kissimmee?

    While on average a flight from Madison to Kissimmee is generally $258, 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 $143 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 February is currently the most expensive (average of $118). 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.

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$116Average$211FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$158Average$361FlexibilityNo cancel feeOn-time62%
DeltaCheapest$193Average$371FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$197Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$198Average$367FlexibilityNo cancel feeOn-time69%

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