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Kissimmee

$27+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 17 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 October 28, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$160
(Expedia)

One-way from

$27
(CheapOair)

Popular in

September

Cheapest in

January

Average price

$353
Provider with most accurate pricing for Milwaukee-Mitchell-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Orlando (ORL) flights.
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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. 10% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 2025.

This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:21 pmMKE - MCO
Nonstop3h 12mFrontier
Mon 12/229:00 amMCO - MKE
Nonstop3h 13mFrontier
Deal found 10/28$162
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:48 pmMKE - MCO
Nonstop3h 11mFrontier
Fri 12/263:14 pmMCO - MKE
Nonstop3h 07mFrontier
Deal found 10/28$164
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:34 amMKE - MCO
Nonstop2h 53mMultiple Airlines
Fri 12/194:14 pmMCO - MKE
Nonstop3h 12mMultiple Airlines
Deal found 10/26$165
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:09 pmMKE - MCO
Nonstop3h 00mFrontier
Sat 12/204:51 pmMCO - MKE
Nonstop3h 12mFrontier
Deal found 10/26$167
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/108:04 pmMKE - MCO
1 stop8h 40mFrontier
Fri 11/146:00 amMCO - MKE
1 stop14h 19mFrontier
Deal found 10/27$169
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:21 pmMKE - MCO
Nonstop3h 12mFrontier
Mon 12/299:00 amMCO - MKE
Nonstop3h 13mFrontier
Deal found 10/27$171
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 12/126:09 pmMKE - MCO
Nonstop3h 00mFrontier
Sun 12/143:02 pmMCO - MKE
Nonstop3h 07mFrontier
Deal found 10/27$173
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1210:34 amMKE - MCO
Nonstop2h 53mSpirit Airlines
Sat 12/205:30 pmMCO - MKE
Nonstop2h 50mSpirit Airlines
Deal found 10/28$175
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 12/218:06 pmMKE - MCO
Nonstop2h 53mFrontier
Fri 12/263:14 pmMCO - MKE
Nonstop3h 07mFrontier
Deal found 10/26$180
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:21 pmMKE - MCO
Nonstop3h 12mFrontier
Mon 12/299:00 amMCO - MKE
Nonstop3h 13mFrontier
Deal found 10/28$183
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:30 pmMKE - MCO
1 stop15h 29mMultiple Airlines
Thu 11/279:49 amMCO - MKE
Nonstop2h 51mMultiple Airlines
Deal found 10/28$185

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 October 28, 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

Mon 2/23

4:15 pm-8:00 pm

Nonstop2h 45m

Orlando

Tue 2/24

7:50 am-11:30 am

1 stop4h 40m

$187

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sat 1/10

12:11 pm-6:25 pm

1 stop5h 14m

Orlando

Sat 1/17

5:30 am-11:09 am

1 stop6h 39m

$197

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Tue 2/10

1:18 pm-9:31 pm

1 stop7h 13m

Orlando

Wed 2/11

7:50 pm-11:46 pm

1 stop4h 56m

$197

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 2/8

3:50 pm-10:00 pm

1 stop5h 10m

Orlando

Sun 2/15

6:05 am-12:15 pm

1 stop7h 10m

$197

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Fri 1/30

3:50 pm-10:00 pm

1 stop5h 10m

Orlando

Sun 2/1

7:05 am-11:30 am

1 stop5h 25m

$197

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Tue 1/6

5:20 am-10:55 am

1 stop4h 35m

Orlando

Tue 1/13

4:20 pm-7:58 pm

1 stop4h 38m

$197

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Fri 1/23

5:30 am-11:20 am

1 stop4h 50m

Orlando

Mon 1/26

8:15 pm-10:15 pm

Nonstop3h 00m

$245

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Sun 2/8

7:00 am-2:05 pm

1 stop6h 05m

Orlando

Sun 2/15

5:30 am-9:27 am

1 stop4h 57m

$248

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Fri 2/27

2:45 pm-10:37 pm

1 stop6h 52m

Orlando

Tue 3/3

5:30 am-9:27 am

1 stop4h 57m

$248

MilwaukeeOrlando

MKE - MCO

MKEMCO

Milwaukee-Mitchell

Wed 2/11

5:20 am-12:02 pm

1 stop5h 42m

Orlando

Wed 2/18

7:50 pm-11:27 pm

1 stop4h 37m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 21 results
1
2
3

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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Milwaukee to Kissimmee, you should look to book at least 17 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, January is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $42). 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 October 28, 2025.

It’s typically best to fly out from Milwaukee to Kissimmee in the evening. Doing so could potentially save you 16% on the flight price compared to flying at noon, 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 October 26, 2025.

Travelers seeking maximum savings on their Milwaukee to Kissimmee flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday 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 October 28, 2025.
Read reviews from past customers who have flown Southwest, American Airlines, and Sun Country Air 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
4,238 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,034 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Sun Country Air
6.9
Okay
335 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,113 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,124 reviews
Southwest
8.0
Very good
4,238 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 is 1 daily outbound flight 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 2h 45m. Southwest provides one of the quickest options available for as low as $187. 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?

    $79 is the cheapest one-way deal found within the past few days, from Sun Country Air. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $89 and $99, respectively.

  • What are the cheapest flights from Milwaukee to Kissimmee?

    The cheapest flight price from Milwaukee to Kissimmee is $85. On average you can expect to pay $273. The most popular route, (Milwaukee-Mitchell - Orlando), can usually be booked for $74.

  • 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, January is the cheapest month in which you can book a flight from Milwaukee to Kissimmee (average of $42). 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$88Average$233FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$97Average$207FlexibilityNo cancel feeOn-time65%
Sun Country AirCheapest$138Average$268FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$150Average$409FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$444FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$456FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$441FlexibilityNo cancel feeOn-time63%

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