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Kissimmee

$135+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheapflights Tip: The best prices from Oshkosh to Kissimmee are usually found in July or August, booked 82 days in advance, depart on a Sunday or Monday 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 September 16, 2025.

Round-trip from

$170
(Kiwi.com)

One-way from

$149
(Delta)

Popular in

March

Cheapest in

July

Average price

$376
From Oshkosh to Kissimmee
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One-way flight from Oshkosh to Kissimmee
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/105:03 pmATW - MCO
1 stop6h 40mMultiple Airlines
Wed 11/195:15 pmMCO - ATW
1 stop29h 16mMultiple Airlines
Deal found 9/14$226
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/175:03 pmATW - MCO
1 stop6h 40mMultiple Airlines
Thu 11/206:55 amMCO - ATW
1 stop15h 36mMultiple Airlines
Deal found 9/15$228
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/274:15 pmATW - MCO
1 stop5h 44mMultiple Airlines
Thu 11/68:05 pmMCO - ATW
1 stop19h 58mMultiple Airlines
Deal found 9/15$231
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/105:03 pmATW - MCO
1 stop13h 57mMultiple Airlines
Thu 11/138:05 pmMCO - ATW
1 stop19h 58mMultiple Airlines
Deal found 9/15$235
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 12/71:53 pmATW - MCO
1 stop19h 11mMultiple Airlines
Thu 12/116:55 amMCO - ATW
1 stop15h 53mMultiple Airlines
Deal found 9/14$237
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/139:00 amATW - MCO
1 stop11h 10mMultiple Airlines
Thu 10/1610:18 pmMCO - ATW
1 stop25h 54mMultiple Airlines
Deal found 9/15$238
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/274:15 pmATW - MCO
1 stop5h 44mMultiple Airlines
Fri 10/318:41 amMCO - ATW
1 stop6h 44mMultiple Airlines
Deal found 9/15$239
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/105:03 pmATW - MCO
1 stop6h 40mMultiple Airlines
Fri 11/147:15 amMCO - ATW
1 stop8h 48mMultiple Airlines
Deal found 9/14$240
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/263:25 pmATW - MCO
1 stop13h 28mMultiple Airlines
Thu 11/68:05 pmMCO - ATW
1 stop19h 58mMultiple Airlines
Deal found 9/15$256
This Delta deal was found by Cheapflights users on 9/15. 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 11/1512:25 pmATW - MCO
1 stop7h 30mDelta
Wed 11/196:55 amMCO - ATW
1 stop5h 38mDelta
Deal found 9/15$259
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/299:53 amATW - MCO
2 stops9h 30mAmerican Airlines
Wed 11/56:46 pmMCO - ATW
1 stop5h 39mAmerican Airlines
Deal found 9/14$264
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 11/84:33 pmATW - MCO
1 stop6h 14mAmerican Airlines
Tue 11/117:00 amMCO - ATW
2 stops9h 17mAmerican Airlines
Deal found 9/14$265

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 September 16, 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 10/25

2:45 pm-12:45 am

2 stops9h 00m

Orlando

Tue 12/2

12:30 pm-4:42 pm

1 stop5h 12m

$264

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sun 1/18

12:06 pm-8:43 pm

1 stop7h 37m

Orlando

Tue 1/27

6:40 am-11:21 am

1 stop5h 41m

$278

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Fri 10/31

4:17 pm-10:56 pm

1 stop5h 39m

Orlando

Wed 11/5

4:30 pm-9:35 pm

1 stop6h 05m

$309

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sun 10/26

4:17 pm-10:56 pm

1 stop5h 39m

Orlando

Tue 12/2

6:35 pm-10:11 pm

1 stop4h 36m

$309

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Mon 10/27

4:17 pm-10:56 pm

1 stop5h 39m

Orlando

Wed 11/5

4:30 pm-9:35 pm

1 stop6h 05m

$309

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sat 10/18

4:57 pm-10:35 pm

1 stop4h 38m

Orlando

Tue 10/21

6:05 am-10:31 am

1 stop5h 26m

$319

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Mon 1/19

4:05 pm-10:54 pm

1 stop5h 49m

Orlando

Thu 1/22

2:25 pm-9:39 pm

1 stop8h 14m

$328

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Tue 10/28

5:41 am-12:14 pm

1 stop5h 33m

Orlando

Tue 11/4

7:20 am-9:15 pm

1 stop14h 55m

$333

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Mon 10/27

4:17 pm-10:56 pm

1 stop5h 39m

Orlando

Tue 11/4

7:20 am-9:15 pm

1 stop14h 55m

$333

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sun 11/23

2:32 pm-12:55 am

2 stops9h 23m

Orlando

Thu 11/27

6:00 am-1:57 pm

2 stops8h 57m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
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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 September 12, 2025.

To ensure you get the cheapest price possible for a flight from Oshkosh to Kissimmee, you should look to book at least 82 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 $206). Flying from Oshkosh 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 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 September 16, 2025.

When flying from Oshkosh 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 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 September 14, 2025.

Travelers seeking maximum savings on their Oshkosh to Kissimmee flight should consider departing on Sunday 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.

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 September 16, 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
8.0
Very good
7,957 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
8.0
Very good
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
8,924 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
10,000 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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
699 reviews
Delta
8.0
Very good
7,957 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Food

7.3

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 7h 37m. United Airlines provides one of the quickest options available for as low as $278. 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 $246, our data shows the cheapest flight currently is $63. When looking at the most popular route, (Appleton Intl - Orlando), you can expect to pay $170 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 $206). Flying from Oshkosh 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.

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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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$87Average$255FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$95Average$204FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$110Average$260FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$207FlexibilityNo cancel feeOn-timeN/A
Sun Country AirCheapest$138Average$272FlexibilityNo cancel feeOn-time83%
DeltaCheapest$193Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$445FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$198Average$434FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$266Average$444FlexibilityNo cancel feeOn-time63%

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