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$98+ 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 12/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/253:05 pmMCO - YWG
1 stop9h 30mMultiple Airlines
Tue 12/308:00 amYWG - MCO
Nonstop4h 07mMultiple Airlines
Deal found 12/10$299
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/2610:00 pmMCO - YWG
Nonstop4h 26mWestJet
Tue 12/308:00 amYWG - MCO
Nonstop4h 07mWestJet
Deal found 12/10$321
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/268:50 amMCO - YWG
1 stop7h 40mMultiple Airlines
Tue 12/308:00 amYWG - MCO
Nonstop4h 07mMultiple Airlines
Deal found 12/10$332
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/134:10 pmMCO - YWG
1 stop23h 57mMultiple Airlines
Mon 12/158:00 amYWG - MCO
1 stop22h 45mMultiple Airlines
Deal found 12/11$385
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:50 amMCO - YWG
1 stop7h 40mMultiple Airlines
Thu 1/88:05 pmYWG - MCO
1 stop23h 17mMultiple Airlines
Deal found 12/10$439
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Wed 12/248:50 amMCO - YWG
1 stop7h 40mMultiple Airlines
Tue 12/308:00 amYWG - MCO
Nonstop4h 07mMultiple Airlines
Deal found 12/10$476
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/253:05 pmMCO - YWG
1 stop9h 30mMultiple Airlines
Wed 12/314:55 pmYWG - MCO
1 stop13h 10mMultiple Airlines
Deal found 12/10$483
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/236:45 amMCO - YWG
2 stops14h 23mMultiple Airlines
Tue 12/308:00 amYWG - MCO
Nonstop4h 07mMultiple Airlines
Deal found 12/10$499
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/2211:20 amMCO - YWG
1 stop9h 15mMultiple Airlines
Tue 12/308:00 amYWG - MCO
Nonstop4h 07mMultiple Airlines
Deal found 12/10$504

Find flight deals from Kissimmee to Winnipeg

Keep the following information in mind while searching for Kissimmee to Winnipeg flight deals. Data was last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$94
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$402
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. 17% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($40 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 December 12, 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

Thu 1/22

7:48 pm-3:07 pm

1 stop20h 19m

Winnipeg

Tue 3/3

12:20 pm-8:16 pm

1 stop6h 56m

$237

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sun 1/25

5:25 am-3:07 pm

1 stop10h 42m

Winnipeg

Sun 2/1

7:30 am-5:52 pm

1 stop9h 22m

$239

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 1/24

11:20 am-7:35 pm

1 stop9h 15m

Winnipeg

Sat 1/31

8:20 pm-10:20 am

1 stop13h 00m

$269

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 1/23

8:30 am-4:35 pm

1 stop9h 05m

Winnipeg

Mon 1/26

5:30 am-5:07 pm

2 stops10h 37m

$281

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 1/24

11:20 am-7:35 pm

1 stop9h 15m

Winnipeg

Sat 1/31

9:00 pm-10:07 am

2 stops12h 07m

$294

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 12/26

8:50 am-3:30 pm

1 stop7h 40m

$98

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 1/15

7:47 pm-3:07 pm

1 stop20h 20m

$100

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 4/24

7:15 pm-11:39 am

1 stop17h 24m

$113

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 1/8

7:35 pm-11:57 am

1 stop17h 22m

$113

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sun 4/26

7:15 pm-11:39 am

1 stop17h 24m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 15 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 December 12, 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 47% 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 December 12, 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
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

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
8,008 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

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
9,095 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

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
3,194 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

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
10,514 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

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 05m. Flair Airlines provides one of the quickest options available for as low as $281. The distance from Kissimmee to Winnipeg is about 1702 mi. This flight may include one or multiple stops.

  • 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: LATAM Airlines (100%), Delta (100%), WestJet( 100%).

  • What are the cheapest flights from Kissimmee to Winnipeg?

    Looking at all options, your cheapest flight can be booked for $257. While the most popular route (Orlando - Winnipeg) can be booked for $226 on average, our data indicates $330 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

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$97Average$366FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$112Average$479FlexibilityNo cancel feeOn-time69%
DeltaCheapest$163Average$445FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$198Average$276FlexibilityNo cancel feeOn-time60%

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