HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$94+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oshkosh to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Oshkosh to Kissimmee are usually found in August or September, booked 29 days in advance, depart on a Tuesday 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 April 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$199
(American Airlines)

One-way from

$94
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$370
Provider with most accurate pricing for Appleton Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Appleton Intl-Orlando (ORL) flights.
Search Deals
From Oshkosh to Kissimmee
Search Deals
One-way flight from Oshkosh to Kissimmee
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals

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 April 25, 2025.

This American Airlines deal was found by Cheapflights users on 4/25. 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 5/244:37 pmATW - MCO
1 stop4h 51mAmerican Airlines
Wed 5/287:15 pmMCO - ATW
1 stop5h 19mAmerican Airlines
Deal found 4/25$199
This Mytrip deal was found by Cheapflights users on 4/25. 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 5/124:26 pmATW - MCO
1 stop16h 58mMultiple Airlines
Fri 5/166:17 amMCO - ATW
1 stop14h 48mMultiple Airlines
Deal found 4/25$202
This Delta deal was found by Cheapflights users on 4/24. 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 5/245:15 pmATW - MCO
1 stop5h 39mDelta
Sat 5/316:00 amMCO - ATW
1 stop5h 31mDelta
Deal found 4/24$217
This United Airlines deal was found by Cheapflights users on 4/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/33:43 pmATW - MCO
1 stop5h 03mUnited Airlines
Wed 6/49:04 amMCO - ATW
2 stops8h 44mUnited Airlines
Deal found 4/24$256

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 April 25, 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 5/24

4:37 pm-10:28 pm

1 stop4h 51m

Orlando

Wed 5/28

7:15 pm-11:34 pm

1 stop5h 19m

$199

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Mon 5/12

4:26 pm-10:24 am

1 stop16h 58m

Orlando

Fri 5/16

6:17 am-8:05 pm

1 stop14h 48m

$202

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sat 5/24

5:15 pm-11:54 pm

1 stop5h 39m

Orlando

Sat 5/31

6:00 am-10:31 am

1 stop5h 31m

$217

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Tue 6/3

3:43 pm-9:46 pm

1 stop5h 03m

Orlando

Wed 6/4

9:04 am-4:48 pm

2 stops8h 44m

$256

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Mon 5/12

4:26 pm-10:46 pm

1 stop5h 20m

$94

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Wed 6/4

4:37 pm-10:28 pm

1 stop4h 51m

$126

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Thu 6/12

4:14 pm-11:53 pm

1 stop6h 39m

$296

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Thu 7/24

8:00 am-7:43 pm

3 stops10h 43m

$1,153

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

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 April 18, 2025.

To ensure you get the cheapest price possible for a flight from Oshkosh to Kissimmee, you should look to book at least 29 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 April 25, 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 December 16, 2024.

Travelers seeking maximum savings on their Oshkosh to Kissimmee flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 April 25, 2025.
Read through reviews of airlines operating flights from Oshkosh to Kissimmee, such as Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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
7,920 reviews

Overall

8.0

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

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.

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

    The cheapest airlines for a one-way flight from Oshkosh to Kissimmee are American Airlines ($126), Delta ($296), and United Airlines ($1,153).

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

    Consider Spirit Airlines (88%), Frontier (88%) or Sun Country Air (76%) when booking your flight. These represent the most reliable airlines when flying from Oshkosh to Kissimmee.

  • What are the cheapest flights from Oshkosh to Kissimmee?

    While on average a flight from Oshkosh to Kissimmee is generally $215, our data shows the cheapest flight currently is $62. When looking at the most popular route, (Appleton Intl - Orlando), you can expect to pay $217 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oshkosh to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Minneapolis to Orlando flights
Minneapolis to Miami flights
O'Hare Intl to Fort Myers flights
Minneapolis to Tampa flights
O'Hare Intl to Sarasota flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to Pensacola flights
Minneapolis to Fort Myers flights
Milwaukee to Orlando flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Panama City flights
Appleton to Orlando flights
Milwaukee to Miami flights
Milwaukee to Tampa flights
Minneapolis to Valparaiso flights
O'Hare Intl to Key West flights
Minneapolis to Sarasota flights
O'Hare Intl to Valparaiso flights
Appleton to Tampa flights
Minneapolis to Pensacola flights
Milwaukee to Fort Myers flights
Milwaukee to Fort Lauderdale flights
Madison to Orlando flights
Appleton to Fort Myers flights
Milwaukee to Sarasota flights
Green Bay to Tampa flights
Appleton to Orlando Sanford Intl flights
Appleton to Sarasota flights
Appleton to Fort Lauderdale flights
Appleton to St Petersburg flights
Green Bay to Orlando flights
Minneapolis to Jacksonville flights
Green Bay to Fort Myers flights
Madison to Fort Myers flights
O'Hare Intl to Daytona Beach flights
Minneapolis to West Palm Beach flights
Milwaukee to Pensacola flights
Milwaukee to West Palm Beach flights
Milwaukee to Panama City flights
Minneapolis to Key West flights
Madison to Tampa flights
Madison to Sarasota flights
Appleton to Pensacola flights
Appleton to Miami flights
Madison to Fort Lauderdale flights

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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$77Average$225FlexibilityNo cancel feeOn-time65%
FrontierCheapest$87Average$236FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$110Average$256FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$117Average$194FlexibilityNo cancel feeOn-timeN/A
Sun Country AirCheapest$125Average$271FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$141Average$425FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$180Average$447FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$411FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$448FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.