HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$81+ Cheap flights from Kissimmee, FL to Winnipeg (YWG)

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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kissimmee to Winnipeg 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.

Find flight deals from Kissimmee to Winnipeg

Cheapest flights from Kissimmee to Winnipeg
Explore the most affordable flight options available from Kissimmee to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Fri 11/286:00 amMCO - YWG
1 stop10h 07mMultiple Airlines
Tue 12/29:00 pmYWG - MCO
2 stops16h 27mMultiple Airlines
Deal found 10/29$204
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/189:00 pmMCO - YWG
1 stop19h 07mMultiple Airlines
Tue 11/258:00 amYWG - MCO
Nonstop4h 07mMultiple Airlines
Deal found 10/26$213
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/288:19 amMCO - YWG
1 stop7h 48mMultiple Airlines
Wed 12/37:30 amYWG - MCO
1 stop25h 46mMultiple Airlines
Deal found 10/28$214
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:16 pmMCO - YWG
1 stop17h 51mMultiple Airlines
Tue 11/119:00 pmYWG - MCO
2 stops12h 09mMultiple Airlines
Deal found 10/28$224
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:30 amMCO - YWG
1 stop10h 37mMultiple Airlines
Sun 12/77:30 amYWG - MCO
1 stop15h 51mMultiple Airlines
Deal found 10/28$225
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:25 amMCO - YWG
1 stop10h 42mMultiple Airlines
Thu 11/139:00 pmYWG - MCO
2 stops12h 02mMultiple Airlines
Deal found 10/28$228
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:25 amMCO - YWG
1 stop10h 42mMultiple Airlines
Wed 11/127:30 amYWG - MCO
1 stop6h 37mMultiple Airlines
Deal found 10/28$232

Cheap flight deals from Kissimmee to Winnipeg

Keep the following information in mind while searching for Kissimmee to Winnipeg flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$204
(Kiwi.com)

One-way from

$81
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$261
Provider with most accurate pricing for Orlando (ORL)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Winnipeg flights.
Search Deals
From Kissimmee to Winnipeg
Search Deals
One-way flight from Kissimmee to Winnipeg
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee to Winnipeg 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 29, 2025.
Use the filters below to find and compare flights from Kissimmee to Winnipeg that are best for you.

Fly from

Kissimmee

Fly to

Winnipeg

Route

Depart

Return

Price

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/28

6:00 am-3:07 pm

1 stop10h 07m

Winnipeg

Tue 12/2

9:00 pm-2:27 pm

2 stops16h 27m

$206

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 1/16

11:10 am-7:12 pm

1 stop9h 02m

Winnipeg

Mon 1/19

12:20 pm-8:22 pm

1 stop7h 02m

$212

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/28

8:19 am-3:07 pm

1 stop7h 48m

Winnipeg

Wed 12/3

7:30 am-10:16 am

1 stop25h 46m

$214

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 12/5

5:30 am-3:07 pm

1 stop10h 37m

Winnipeg

Sun 12/7

7:30 am-12:21 am

1 stop15h 51m

$225

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/7

5:25 am-3:07 pm

1 stop10h 42m

Winnipeg

Thu 11/13

9:00 pm-10:02 am

2 stops12h 02m

$228

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/7

5:25 am-3:07 pm

1 stop10h 42m

Winnipeg

Wed 11/12

7:30 am-3:07 pm

1 stop6h 37m

$232

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 12/12

5:30 am-3:07 pm

1 stop10h 37m

$81

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 11/1

7:36 pm-4:07 pm

1 stop21h 31m

$95

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/14

5:25 am-12:41 am

2 stops20h 16m

$98

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 12/26

7:15 am-7:34 pm

2 stops13h 19m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 11 results
1
2

Best time to book a flight from Kissimmee to Winnipeg

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

What is the cheapest month to book a flight from Kissimmee to Winnipeg?

Currently, May is the cheapest month in which you can book a flight from Kissimmee to Winnipeg (average of $109). Flying from Kissimmee to Winnipeg in June is currently the most expensive (average of $341). 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 K1S to YWG?

Find hourly flight availability from Kissimmee to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Kissimmee to Winnipeg at noon. If you’re flexible enough to do this you can expect to save up to 46% on your trip compared to booking a flight in the morning.

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated October 29, 2025.
See what other customers who have flown with Delta, United Airlines, and WestJet from Kissimmee to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,994 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
WestJet
7.2
Good
3,148 reviews
Delta
7.9
Good
7,994 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Air Canada
7.1
Good
10,371 reviews
Delta
7.9
Good
7,994 reviews

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Kissimmee to Winnipeg. 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 into for flights to Winnipeg from Kissimmee?

    Winnipeg (YWG) is the airport you will fly into if you book a flight from Kissimmee to Winnipeg. You should not have trouble finding flights to Winnipeg from Kissimmee; the airport handles an average of 0 inbound flights from Kissimmee per day. You should also have plenty of airline options to choose from since 4 airlines have flights to the Winnipeg airport from Kissimmee. It is only a 4.6 mi journey from Winnipeg (YWG) to Winnipeg’s city center.

  • How long is the flight from Kissimmee to Winnipeg?

    A quick flight from Kissimmee to Winnipeg can take about 9h 02m. WestJet provides one of the quickest options available for as low as $212. The distance from Kissimmee to Winnipeg is about 1702 mi.

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

    Before booking your flight to Winnipeg from Kissimmee, check out the most reliable airlines to get you to your destination on time: Delta (100%), WestJet (100%), Aeromexico( 100%).

  • What are the cheapest flights from Kissimmee to Winnipeg?

    Looking at all options, your cheapest flight can be booked for $191. While the most popular route (Orlando - Winnipeg) can be booked for $204 on average, our data indicates $191 when flying from Kissimmee to Winnipeg.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Kissimmee to Winnipeg (average of $109). Flying from Kissimmee to Winnipeg in June is currently the most expensive (average of $341). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

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.

Top 4 airlines flying from Kissimmee to Winnipeg

Discover the top 4 airlines that operate flights from Kissimmee to Winnipeg. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$101Average$366FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$112Average$479FlexibilityNo cancel feeOn-time69%
WestJetCheapest$198Average$276FlexibilityNo cancel feeOn-time60%
DeltaCheapest$229Average$465FlexibilityNo cancel feeOn-timeN/A

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.