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Kissimmee

$53+ 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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Aug 16 — Aug 231
Sat 8/16
Sat 8/23
1 adult, Economy
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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Kissimmee are usually found in January or February, booked 49 days in advance, depart on a Tuesday or Thursday and return on a Thursday

Cheap flight deals from Milwaukee to Kissimmee

Keep the following information in mind while searching for Milwaukee to Kissimmee flight deals. Data was last updated August 11, 2025.

Round-trip from

$108
(Cheapflightsfares)

One-way from

$53
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$281
From Milwaukee-Mitchell to Kissimmee
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One-way flight from Milwaukee-Mitchell to Kissimmee
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Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 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 August 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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 10/1912:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Thu 10/2310:00 amMCO - MKE
Nonstop2h 58mSpirit Airlines
Deal found 8/9$108
This Cheapflightsfares deal was found by Cheapflights users on 8/11. 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 9/712:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Thu 9/1110:00 amMCO - MKE
Nonstop2h 58mSpirit Airlines
Deal found 8/11$118
This Priceline deal was found by Cheapflights users on 8/9. 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 9/36:00 amMKE - MCO
Nonstop2h 47mSpirit Airlines
Thu 9/1810:00 amMCO - MKE
Nonstop2h 58mSpirit Airlines
Deal found 8/9$120
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Thu 9/1812:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Sun 9/2110:00 amMCO - MKE
Nonstop2h 58mSpirit Airlines
Deal found 8/9$127
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Sun 10/1912:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Thu 11/69:05 amMCO - MKE
Nonstop2h 57mSpirit Airlines
Deal found 8/9$128
This FlightHub deal was found by Cheapflights users on 8/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1112:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Sun 9/1410:00 amMCO - MKE
Nonstop2h 58mSpirit Airlines
Deal found 8/10$138
This Mytrip deal was found by Cheapflights users on 8/9. 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.
Sun 9/712:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Sun 9/1410:00 amMCO - MKE
Nonstop2h 58mSpirit Airlines
Deal found 8/9$140
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Thu 8/286:00 amMKE - MCO
Nonstop2h 47mSpirit Airlines
Tue 9/29:10 pmMCO - MKE
Nonstop2h 56mSpirit Airlines
Deal found 8/9$148
This Cheapflightsfares deal was found by Cheapflights users on 8/9. 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 11/911:57 amMKE - MCO
Nonstop2h 45mSpirit Airlines
Fri 11/147:15 amMCO - MKE
1 stop5h 14mSpirit Airlines
Deal found 8/9$151
This Cheapflightsfares deal was found by Cheapflights users on 8/10. 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.
Tue 8/266:00 amMKE - MCO
Nonstop2h 47mSpirit Airlines
Wed 8/279:10 pmMCO - MKE
Nonstop2h 56mSpirit Airlines
Deal found 8/10$158
This Kiwi.com deal was found by Cheapflights users on 8/9. 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.
Sun 8/246:00 amMKE - MCO
Nonstop2h 47mSpirit Airlines
Tue 8/269:10 pmMCO - MKE
Nonstop2h 56mSpirit Airlines
Deal found 8/9$168
This FlightHub deal was found by Cheapflights users on 8/9. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:53 pmMKE - MCO
Nonstop2h 46mSpirit Airlines
Sun 11/26:55 pmMCO - MKE
1 stop16h 38mSpirit Airlines
Deal found 8/9$172

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 August 11, 2025.
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

Sun 10/19

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Thu 10/23

10:00 am-11:58 am

Nonstop2h 58m

$108

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 9/7

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Thu 9/11

10:00 am-11:58 am

Nonstop2h 58m

$118

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Wed 9/3

6:00 am-9:47 am

Nonstop2h 47m

Orlando

Thu 9/18

10:00 am-11:58 am

Nonstop2h 58m

$120

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 10/26

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Wed 12/3

9:05 am-11:02 am

Nonstop2h 57m

$126

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Thu 9/18

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Sun 9/21

10:00 am-11:58 am

Nonstop2h 58m

$127

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 10/19

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Thu 11/6

9:05 am-11:02 am

Nonstop2h 57m

$128

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Thu 9/11

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Sun 9/14

10:00 am-11:58 am

Nonstop2h 58m

$138

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 9/7

12:53 pm-4:39 pm

Nonstop2h 46m

Orlando

Sun 9/14

10:00 am-11:58 am

Nonstop2h 58m

$140

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Thu 8/28

6:00 am-9:47 am

Nonstop2h 47m

Orlando

Tue 9/2

9:10 pm-11:06 pm

Nonstop2h 56m

$148

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 11/9

11:57 am-3:42 pm

Nonstop2h 45m

Orlando

Fri 11/14

7:15 am-11:29 am

1 stop5h 14m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/10

Showing 1-10 of 22 results
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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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Milwaukee to Kissimmee, you should look to book at least 49 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, May is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $206). Flying from Milwaukee 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 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 August 11, 2025.

When flying from Milwaukee to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 10, 2025.

Travelers seeking maximum savings on their Milwaukee to Kissimmee flight should consider departing on Tuesday at noon 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.

How much does it cost to fly round-trip from Milwaukee 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 August 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,978 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,922 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Sun Country Air
6.9
Okay
333 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 3 daily outbound flights to Kissimmee from 7 different airlines.

  • What are the cheapest flights from Milwaukee to Kissimmee?

    The cheapest flight price from Milwaukee to Kissimmee is $71. On average you can expect to pay $210. The most popular route, (Milwaukee-Mitchell - Orlando), can usually be booked for $108.

  • 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, May is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $206). Flying from Milwaukee 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 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 August 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$87Average$228FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$203FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$138Average$279FlexibilityNo cancel feeOn-time83%
American AirlinesCheapest$177Average$444FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$431FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$208Average$445FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$275Average$443FlexibilityNo cancel feeOn-time63%

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