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Kissimmee

$44+ Cheap flights from Milwaukee (MKE) 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Kissimmee are usually found in January or July, booked 78 days in advance, depart on a Thursday or Tuesday and return on a Wednesday

Cheap flight deals from Milwaukee to Kissimmee

Cheapest flights from Milwaukee to Kissimmee
Explore the most affordable flight options available from Milwaukee to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:11 pm
MKE
-
MCO
Nonstop2h 55m
Frontier
Fri 2/277:25 am
MCO
-
MKE
Nonstop3h 18m
Frontier
Deal found 1/27$119
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:01 pm
MKE
-
MCO
Nonstop2h 55m
Frontier
Thu 3/125:20 am
MCO
-
MKE
Nonstop3h 10m
Frontier
Deal found 1/28$127
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:37 pm
MKE
-
MCO
Nonstop2h 50m
Frontier
Fri 2/277:25 am
MCO
-
MKE
Nonstop3h 18m
Frontier
Deal found 1/28$129
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:39 pm
MKE
-
MCO
Nonstop2h 50m
Frontier
Fri 3/69:27 am
MCO
-
MKE
Nonstop3h 14m
Frontier
Deal found 1/28$132
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:11 pm
MKE
-
MCO
Nonstop2h 55m
Frontier
Thu 2/264:28 pm
MCO
-
MKE
Nonstop3h 14m
Frontier
Deal found 1/28$134
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/147:47 pm
MKE
-
MCO
Nonstop2h 52m
Frontier
Fri 2/207:25 am
MCO
-
MKE
Nonstop3h 18m
Frontier
Deal found 1/27$138
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.
Tue 2/104:42 pm
MKE
-
MCO
Nonstop2h 55m
Frontier
Fri 2/137:25 am
MCO
-
MKE
Nonstop3h 18m
Frontier
Deal found 1/27$142
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:11 pm
MKE
-
MCO
Nonstop2h 55m
Frontier
Thu 3/58:29 pm
MCO
-
MKE
1 stop23h 22m
Frontier
Deal found 1/28$143
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:37 pm
MKE
-
MCO
Nonstop2h 50m
Frontier
Wed 2/251:28 pm
MCO
-
MKE
Nonstop3h 16m
Frontier
Deal found 1/27$144
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/226:37 pm
MKE
-
MCO
Nonstop2h 50m
Frontier
Sat 2/284:38 pm
MCO
-
MKE
Nonstop3h 14m
Frontier
Deal found 1/28$145

Find flight deals from Milwaukee to Kissimmee

Keep the following information in mind while searching for Milwaukee 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

$119
(Frontier)

One-way from

$44
(Super.com)

Popular in

September

Cheapest in

January

Average price

$225
Provider with most accurate pricing for Milwaukee-Mitchell-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Orlando (ORL) flights.
Search Deals
From Milwaukee-Mitchell to Kissimmee
Search Deals
One-way flight from Milwaukee-Mitchell to Kissimmee
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($28 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 January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 Milwaukee to Kissimmee that are best for you.

Fly from

Milwaukee

Fly to

Kissimmee

Route

Depart

Return

Price

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Tue 2/24

5:25 am-10:55 am

1 stop4h 30m

Orlando

Tue 2/24

5:30 pm-11:47 pm

1 stop7h 17m

$257

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Mon 3/2

6:29 pm-12:59 am

1 stop5h 30m

Orlando

Tue 3/3

7:00 am-12:31 pm

1 stop6h 31m

$268

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Fri 2/20

11:55 am-9:35 pm

1 stop8h 40m

Orlando

Mon 2/23

4:50 pm-10:35 pm

1 stop6h 45m

$277

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Mon 2/23

4:30 pm-10:20 pm

1 stop4h 50m

Orlando

Mon 3/30

9:50 pm-11:50 pm

Nonstop3h 00m

$280

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 3/1

6:29 pm-12:03 am

1 stop4h 34m

Orlando

Fri 3/6

7:38 pm-11:47 pm

1 stop5h 09m

$302

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Thu 2/19

3:10 pm-10:50 pm

1 stop6h 40m

Orlando

Tue 2/24

8:15 pm-10:15 pm

Nonstop3h 00m

$307

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Wed 4/15

12:32 pm-6:45 pm

1 stop5h 13m

Orlando

Tue 4/21

6:15 am-11:27 am

1 stop6h 12m

$321

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sat 2/21

12:15 pm-8:00 pm

2 stops6h 45m

Orlando

Sat 2/28

8:00 am-1:50 pm

1 stop6h 50m

$322

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Mon 4/6

3:00 pm-6:45 pm

Nonstop2h 45m

Orlando

Thu 4/9

7:40 am-9:40 am

Nonstop3h 00m

$323

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sat 4/11

5:40 am-12:30 pm

2 stops5h 50m

Orlando

Wed 4/15

6:50 am-8:45 am

Nonstop2h 55m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 results
1
2

Best time to book a flight from Milwaukee to Kissimmee

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

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

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

To ensure you get the cheapest price possible for a flight from Milwaukee to Kissimmee, you should look to book at least 78 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, March is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $53). Flying from Milwaukee to Kissimmee in June is currently the most expensive (average of $108). 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 MKE to K1S?

Find hourly flight availability from Milwaukee 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.

It’s typically best to fly out from Milwaukee to Kissimmee in the afternoon. Doing so could potentially save you 21% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Kissimmee. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Milwaukee to Kissimmee flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday mornings 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 January 29, 2026.
Read reviews from past customers who have flown Southwest, Delta, and American Airlines from Milwaukee 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.
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,393 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

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

    Located just 6.4 mi from the city center, Milwaukee-Mitchell is the airport most travelers will use when flying to Kissimmee from Milwaukee. Booking flights from Milwaukee-Mitchell (MKE) to Kissimmee should be relatively easy as there are 2 daily outbound flights to Kissimmee from 7 different airlines.

  • How long is the flight from Milwaukee to Kissimmee?

    A quick flight from Milwaukee to Kissimmee can take about 4h 30m. Delta provides one of the quickest options available for as low as $257. Milwaukee and Kissimmee are separated by a distance of 1067 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    $38 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and Sun Country Air, with prices starting from $46 and $69, respectively.

  • What are the most reliable airlines from Milwaukee to Kissimmee?

    No one likes to see their flight delayed. When booking a flight from Milwaukee to Kissimmee consider choosing Spirit Airlines (92%), Frontier (70%) or Southwest (70%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Milwaukee to Kissimmee?

    The cheapest flight price from Milwaukee to Kissimmee is $43. On average you can expect to pay $229. The most popular route, (Milwaukee-Mitchell - Orlando), can usually be booked for $157.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to Kissimmee?

    Currently, March is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $53). Flying from Milwaukee to Kissimmee in June is currently the most expensive (average of $108). 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 7 airlines flying from Milwaukee to Kissimmee

Discover the top 7 airlines that operate flights from Milwaukee 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
FrontierCheapest$75Average$233FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$87Average$200FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$114Average$258FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$150Average$398FlexibilityNo cancel feeOn-time69%
DeltaCheapest$184Average$438FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$190Average$447FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$256Average$432FlexibilityNo cancel feeOn-time63%

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