HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$96+ 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January or July, booked 42 days in advance, depart on a Monday or Friday and return on a Monday

Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/33:17 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 5/78:08 pm
MCO
-
ATW
Nonstop3h 09m
Allegiant Air
Deal found 1/27$173
This Booking.com deal was found by Cheapflights users on 1/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/303:17 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 5/78:08 pm
MCO
-
ATW
Nonstop3h 09m
Allegiant Air
Deal found 1/27$183
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:44 pm
ATW
-
MCO
Nonstop3h 01m
Multiple Airlines
Thu 5/286:00 am
MCO
-
ATW
1 stop27h 51m
Multiple Airlines
Deal found 1/28$184
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 2/12:23 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 2/57:14 pm
MCO
-
ATW
Nonstop3h 17m
Allegiant Air
Deal found 1/29$190
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/103:17 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 5/148:08 pm
MCO
-
ATW
Nonstop3h 09m
Allegiant Air
Deal found 1/27$193
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/12:23 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 5/78:08 pm
MCO
-
ATW
Nonstop3h 09m
Allegiant Air
Deal found 1/27$194
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:44 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Sun 5/317:35 pm
MCO
-
ATW
Nonstop3h 17m
Allegiant Air
Deal found 1/27$196
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/103:17 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Sun 5/178:08 pm
MCO
-
ATW
Nonstop3h 09m
Allegiant Air
Deal found 1/27$206
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/292:23 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 2/57:14 pm
MCO
-
ATW
Nonstop3h 17m
Allegiant Air
Deal found 1/27$210
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/82:23 pm
ATW
-
MCO
Nonstop3h 01m
Allegiant Air
Thu 2/127:08 pm
MCO
-
ATW
Nonstop3h 09m
Allegiant Air
Deal found 1/27$211

Find flight deals from Oshkosh to Kissimmee

Keep the following information in mind while searching for Oshkosh to Kissimmee flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$173
(Kiwi.com)

One-way from

$96
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$283
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. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Sun 4/26

5:30 pm-11:52 pm

1 stop5h 22m

Orlando

Sat 5/2

7:15 am-11:54 am

1 stop5h 39m

$279

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Tue 7/7

4:05 pm-11:59 pm

1 stop6h 54m

Orlando

Tue 7/14

6:40 am-11:11 am

1 stop5h 31m

$279

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Fri 7/10

4:05 pm-11:59 pm

1 stop6h 54m

Orlando

Wed 7/15

6:40 am-11:11 am

1 stop5h 31m

$279

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Sat 2/21

3:42 pm-9:40 pm

1 stop4h 58m

Orlando

Fri 2/27

7:00 am-1:58 pm

1 stop7h 58m

$279

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Tue 4/21

3:46 pm-9:58 pm

1 stop5h 12m

Orlando

Tue 4/28

7:38 am-11:48 am

1 stop5h 10m

$279

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Tue 3/10

11:14 am-4:52 pm

1 stop4h 38m

Orlando

Wed 3/18

6:00 am-10:32 am

1 stop5h 32m

$279

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Wed 4/1

5:17 am-10:55 am

1 stop4h 38m

Orlando

Thu 4/9

6:00 am-11:25 am

1 stop6h 25m

$296

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Wed 5/20

7:00 am-12:45 pm

1 stop4h 45m

Orlando

Wed 5/27

5:25 pm-9:58 pm

1 stop5h 33m

$299

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Mon 4/20

4:20 pm-10:58 pm

1 stop5h 38m

Orlando

Wed 4/29

6:53 am-11:24 am

1 stop5h 31m

$299

AppletonOrlando

ATW - MCO

ATWMCO

Appleton Intl

Fri 5/1

3:45 pm-12:59 am

2 stops8h 14m

Orlando

Thu 5/7

9:02 am-2:01 pm

1 stop5h 59m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Oshkosh to Kissimmee, you should look to book at least 42 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 $153). 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 January 29, 2026.

It’s typically best to fly out from Oshkosh to Kissimmee in the afternoon. Doing so could potentially save you 31% 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 January 24, 2026.

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 January 29, 2026.
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
8,127 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Food

7.2

Overall

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
8,127 reviews
Delta
7.9
Good
8,127 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Food

7.2

Overall

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
9,215 reviews
Delta
7.9
Good
8,127 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Food

7.2

Overall

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
11,206 reviews
Delta
7.9
Good
8,127 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Food

7.2

Overall

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
706 reviews
Delta
7.9
Good
8,127 reviews

Crew

8.5

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Food

7.2

Overall

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 5h 22m. United Airlines provides one of the quickest options available for as low as $279. 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 airlines to fly from Oshkosh to Kissimmee one-way?

    The cheapest airlines for a one-way flight from Oshkosh to Kissimmee are Allegiant Air ($66), Delta ($149), and United Airlines ($181).

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

    Consider Spirit Airlines (92%), Frontier (70%) or Southwest (70%) 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 $229, our data shows the cheapest flight currently is $43. When looking at the most popular route, (Appleton Intl - Orlando), you can expect to pay $98 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 $153). 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.
Minneapolis to Orlando flights
O'Hare Intl to Fort Lauderdale flights
Minneapolis to Fort Myers flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
O'Hare Intl to Tampa flights
Minneapolis to Tampa flights
Minneapolis to Miami flights
O'Hare Intl to Fort Myers flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Sarasota flights
Milwaukee to Orlando flights
Minneapolis to Sarasota flights
O'Hare Intl to Key West flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Pensacola flights
Milwaukee to Miami flights
Milwaukee to Tampa flights
Milwaukee to Fort Myers flights
Minneapolis to Valparaiso flights
Appleton to Fort Myers flights
Minneapolis to West Palm Beach flights
Milwaukee to Fort Lauderdale flights
O'Hare Intl to Panama City flights
Minneapolis to Pensacola flights
Madison to Sarasota flights
Madison to Orlando flights
Appleton to Pensacola flights
Appleton to Tampa flights
Minneapolis to St Petersburg flights
Minneapolis to Jacksonville flights
Madison to Fort Myers flights
Minneapolis to Daytona Beach flights
Appleton to Orlando flights
Green Bay to Pensacola flights
Madison to Tampa flights
Minneapolis to Panama City flights
Milwaukee to Sarasota flights
Appleton to Orlando Sanford Intl flights
Minneapolis to Key West flights
Green Bay to Fort Myers flights
Appleton to Sarasota flights
Madison to Miami flights
Appleton to St Petersburg flights
Milwaukee to West Palm Beach flights
O'Hare Intl to Valparaiso flights
Green Bay to Tampa flights
O'Hare Intl to Daytona Beach 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$75Average$251FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$87Average$200FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$111Average$257FlexibilityNo cancel feeOn-time88%
Sun Country AirCheapest$114Average$258FlexibilityNo cancel feeOn-time83%
Breeze AirwaysCheapest$118Average$221FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$118Average$404FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$150Average$378FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$190Average$429FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$256Average$432FlexibilityNo 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.