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Kissimmee

$106+ Cheap flights from Oshkosh, WI 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheapflights Tip: The best prices from Oshkosh to Kissimmee are usually found in July or August, booked 19 days in advance, depart on a Friday or Saturday and return on a Wednesday

Cheap flight deals from Oshkosh to Kissimmee

Keep the following information in mind while searching for Oshkosh to Kissimmee flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$188
(Kiwi.com)

One-way from

$106
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$450
Provider with most accurate pricing for Appleton Intl-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Appleton Intl-Orlando (ORL) flights.
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From Oshkosh to Kissimmee
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One-way flight from Oshkosh to Kissimmee
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Highest demand for flights based on searches. 10% potential increase in price ($45 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Oshkosh to Kissimmee

Cheapest flights from Oshkosh to Kissimmee
Explore the most affordable flight options available from Oshkosh to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/111:53 pmATW - MCO
1 stop16h 52mMultiple Airlines
Wed 12/179:01 pmMCO - ATW
1 stop25h 56mMultiple Airlines
Deal found 11/2$212
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Mon 12/155:29 pmATW - MCO
1 stop14h 12mMultiple Airlines
Wed 12/179:01 pmMCO - ATW
1 stop25h 56mMultiple Airlines
Deal found 11/1$227
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Fri 12/125:29 pmATW - MCO
1 stop14h 12mMultiple Airlines
Wed 12/179:01 pmMCO - ATW
1 stop25h 56mMultiple Airlines
Deal found 11/1$231
This Mytrip deal was found by Cheapflights users on 11/2. 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 11/231:53 pmATW - MCO
1 stop8h 48mMultiple Airlines
Sun 11/307:50 pmMCO - ATW
1 stop15h 11mMultiple Airlines
Deal found 11/2$235
This Mytrip deal was found by Cheapflights users on 11/1. 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.
Mon 12/110:51 amATW - MCO
1 stop6h 37mMultiple Airlines
Thu 1/86:55 amMCO - ATW
1 stop16h 20mMultiple Airlines
Deal found 11/1$238
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 12/141:53 pmATW - MCO
1 stop16h 52mMultiple Airlines
Mon 12/227:34 pmMCO - ATW
1 stop20h 46mMultiple Airlines
Deal found 11/2$240
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/111:53 pmATW - MCO
1 stop16h 52mMultiple Airlines
Thu 12/186:45 amMCO - ATW
1 stop16h 12mMultiple Airlines
Deal found 10/31$248

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oshkosh 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 November 3, 2025.
Use the filters below to find and compare flights from Oshkosh to Kissimmee that are best for you.

Fly from

Oshkosh

Fly to

Kissimmee

Route

Depart

Return

Price

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sat 12/13

4:18 pm-12:08 am

1 stop6h 50m

Orlando

Sat 12/20

7:00 am-11:32 am

1 stop5h 32m

$259

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sat 2/21

2:39 pm-9:40 pm

1 stop6h 01m

Orlando

Fri 2/27

7:18 am-1:58 pm

1 stop7h 40m

$259

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Thu 12/11

4:18 pm-12:08 am

1 stop6h 50m

Orlando

Sat 12/20

6:00 am-11:32 am

1 stop6h 32m

$259

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Wed 1/7

2:45 pm-9:50 pm

1 stop6h 05m

Orlando

Mon 1/12

10:25 am-4:48 pm

1 stop7h 23m

$259

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Fri 12/12

4:18 pm-12:08 am

1 stop6h 50m

Orlando

Mon 12/15

8:50 am-3:38 pm

1 stop7h 48m

$259

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Thu 1/22

2:45 pm-9:50 pm

1 stop6h 05m

Orlando

Wed 1/28

7:45 am-3:04 pm

2 stops8h 19m

$264

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sat 1/3

1:00 pm-9:41 pm

1 stop7h 41m

Orlando

Sat 1/10

11:05 am-4:48 pm

2 stops6h 43m

$264

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Wed 12/10

2:32 pm-12:44 am

2 stops9h 12m

Orlando

Sun 12/14

9:25 am-1:57 pm

1 stop5h 32m

$264

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sun 2/1

2:45 pm-12:45 am

2 stops9h 00m

Orlando

Fri 2/13

2:50 pm-7:33 pm

1 stop5h 43m

$264

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sun 4/12

3:17 pm-7:18 pm

Nonstop3h 01m

$116

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 19 results
1
2

Best time to book a flight from Oshkosh to Kissimmee

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

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

Use this chart to determine the optimal time to book a round-trip flight from Oshkosh to Kissimmee. Price data was last updated on October 31, 2025.

To ensure you get the cheapest price possible for a flight from Oshkosh to Kissimmee, you should look to book at least 19 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 Oshkosh to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Oshkosh to Kissimmee (average of $71). Flying from Oshkosh to Kissimmee in October is currently the most expensive (average of $150). 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 OS9 to K1S?

Find hourly flight availability from Oshkosh 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 November 3, 2025.

It’s typically best to fly out from Oshkosh to Kissimmee in the evening. Doing so could potentially save you 10% on the flight price compared to flying at noon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Oshkosh to Kissimmee. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Oshkosh to Kissimmee flight should consider departing on Monday mornings when fares are most often at their lowest. Friday at noon 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 November 3, 2025.
Read through reviews of airlines operating flights from Oshkosh to Kissimmee, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,002 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,997 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,038 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Allegiant Air
7.2
Good
694 reviews
Delta
7.9
Good
8,002 reviews

Food

7.3

Overall

7.9

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Oshkosh to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oshkosh to Kissimmee?

    A quick flight from Oshkosh to Kissimmee can take about 6h 01m. Delta provides one of the quickest options available for as low as $259. The distance between Oshkosh and Kissimmee is about 1163 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Oshkosh to Kissimmee?

    While on average a flight from Oshkosh to Kissimmee is generally $273, our data shows the cheapest flight currently is $85. When looking at the most popular route, (Appleton Intl - Orlando), you can expect to pay $189 for that flight.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Oshkosh to Kissimmee (average of $71). Flying from Oshkosh to Kissimmee in October is currently the most expensive (average of $150). 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 9 airlines flying from Oshkosh to Kissimmee

Discover the top 9 airlines that operate flights from Oshkosh 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$90Average$266FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$97Average$207FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$110Average$245FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$212FlexibilityNo cancel feeOn-timeN/A
Sun Country AirCheapest$138Average$265FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$150Average$410FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$443FlexibilityNo cancel feeOn-time71%
DeltaCheapest$193Average$409FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$441FlexibilityNo cancel feeOn-time63%

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