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Kissimmee

$70+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MCO
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Kissimmee are usually found in August or May, booked 9 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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$139
(CheapOair)

One-way from

$70
(CheapOair)

Popular in

March

Cheapest in

August

Average price

$281
Provider with most accurate pricing for Madison Truax Field-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Orlando (ORL) flights.
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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 ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:05 pmMSN - MCO
Nonstop2h 50mBreeze Airways
Sat 5/312:10 pmMCO - MSN
Nonstop3h 09mBreeze Airways
Deal found 4/29$139
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/285:00 amMSN - MCO
1 stop6h 14mAmerican Airlines
Sat 5/317:37 pmMCO - MSN
1 stop5h 08mAmerican Airlines
Deal found 4/29$199
This Priceline deal was found by Cheapflights users on 4/29. 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 5/187:56 pmMSN - MCO
1 stop9h 07mMultiple Airlines
Wed 5/212:10 pmMCO - MSN
Nonstop3h 09mMultiple Airlines
Deal found 4/29$205
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/47:56 pmMSN - MCO
1 stop9h 07mFrontier
Sat 5/108:59 pmMCO - MSN
1 stop23h 07mFrontier
Deal found 4/29$218
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 7/126:45 amMSN - MCO
1 stop5h 55mDelta
Wed 7/166:55 amMCO - MSN
1 stop5h 16mDelta
Deal found 4/29$251
This United Airlines deal was found by Cheapflights users on 4/29. 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 6/38:20 amMSN - MCO
1 stop5h 36mUnited Airlines
Tue 6/1011:55 amMCO - MSN
2 stops8h 21mUnited Airlines
Deal found 4/29$256
This Sun Country Air deal was found by Cheapflights users on 4/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/132:40 pmMSN - MCO
2 stops18h 55mSun Country Air
Sun 11/237:35 pmMCO - MSN
2 stops19h 07mSun Country Air
Deal found 4/29$463

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 May 1, 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

Wed 5/28

5:05 pm-8:55 pm

Nonstop2h 50m

Orlando

Sat 5/31

2:10 pm-4:19 pm

Nonstop3h 09m

$139

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Wed 5/28

5:00 am-12:14 pm

1 stop6h 14m

Orlando

Sat 5/31

7:37 pm-11:45 pm

1 stop5h 08m

$199

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sun 5/18

7:56 pm-6:03 am

1 stop9h 07m

Orlando

Wed 5/21

2:10 pm-4:19 pm

Nonstop3h 09m

$205

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 7/12

6:45 am-1:40 pm

1 stop5h 55m

Orlando

Wed 7/16

6:55 am-11:11 am

1 stop5h 16m

$251

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Tue 6/3

8:20 am-2:56 pm

1 stop5h 36m

Orlando

Tue 6/10

11:55 am-7:16 pm

2 stops8h 21m

$256

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sun 6/22

7:10 pm-5:44 am

1 stop9h 34m

Orlando

Thu 6/26

6:00 am-6:25 pm

1 stop13h 25m

$442

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 6/28

10:19 am-2:09 pm

Nonstop2h 50m

$70

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 5/31

4:18 pm-12:33 am

1 stop7h 15m

$109

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sun 6/1

7:48 pm-6:02 am

1 stop9h 14m

$129

MadisonOrlando

MSN - MCO

MSNMCO

Madison Truax Field

Sat 5/31

8:31 am-6:42 pm

2 stops9h 11m

$145

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 12 results
1
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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 April 25, 2025.

Booking 9 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 May 1, 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 March 30, 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.

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 May 1, 2025.
To help decide which airline to fly from Madison to Kissimmee, see what other customers have to say about Breeze Airways, Delta and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,934 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,696 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Frontier
6.0
Okay
3,287 reviews
Breeze Airways
8.1
Very good
160 reviews

Crew

8.8

Entertainment

6.6

Comfort

8.2

Boarding

8.3

Food

6.7

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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. 6 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.

  • 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 ($70), American Airlines ($100), and Delta ($109).

  • What are the cheapest flights from Madison to Kissimmee?

    While on average a flight from Madison to Kissimmee is generally $121, our data shows the cheapest flight currently is $69. When looking at the most popular route, (Madison Truax Field - Orlando), you can expect to pay $139 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 6 airlines flying from Madison to Kissimmee

Discover the top 6 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$106Average$253FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$116Average$196FlexibilityNo cancel feeOn-timeN/A
Allegiant AirCheapest$148Average$254FlexibilityNo cancel feeOn-time88%
DeltaCheapest$198Average$398FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$198Average$410FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$227Average$411FlexibilityNo cancel feeOn-time71%

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