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$76+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$179
(Kiwi.com)

One-way from

$76
(Trip.com)

Popular in

April

Cheapest in

October

Average price

$320
From Kissimmee to Winnipeg
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One-way flight from Kissimmee to Winnipeg
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Highest demand for flights based on searches. 12% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($38 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 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 September 15, 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.
Sat 10/113:15 pmMCO - YWG
Nonstop4h 17mWestJet
Sat 10/189:10 amYWG - MCO
Nonstop4h 00mWestJet
Deal found 9/14$179
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 11/2110:00 pmMCO - YWG
Nonstop4h 26mWestJet
Wed 11/2612:20 pmYWG - MCO
1 stop7h 02mWestJet
Deal found 9/12$203
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3110:00 pmMCO - YWG
Nonstop4h 26mWestJet
Tue 11/118:00 amYWG - MCO
Nonstop4h 07mWestJet
Deal found 9/14$212
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.
Sat 10/113:15 pmMCO - YWG
Nonstop4h 17mMultiple Airlines
Sat 10/1810:45 amYWG - MCO
2 stops11h 14mMultiple Airlines
Deal found 9/14$225
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 10/265:15 pmMCO - YWG
1 stop19h 54mWestJet
Fri 10/314:00 pmYWG - MCO
Nonstop4h 03mWestJet
Deal found 9/14$227
This Trip.com deal was found by Cheapflights users on 9/13. 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.
Mon 10/279:15 pmMCO - YWG
1 stop28h 27mWestJet
Mon 11/312:20 pmYWG - MCO
1 stop7h 02mWestJet
Deal found 9/13$228
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 10/275:00 pmMCO - YWG
2 stops19h 13mMultiple Airlines
Mon 11/312:20 pmYWG - MCO
1 stop7h 02mMultiple Airlines
Deal found 9/13$243

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 September 15, 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

Mon 10/27

9:15 pm-12:42 am

1 stop28h 27m

Winnipeg

Mon 11/3

12:20 pm-8:22 pm

1 stop7h 02m

$228

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 3/10

8:30 am-4:35 pm

1 stop9h 05m

Winnipeg

Wed 3/11

8:15 am-5:07 pm

1 stop7h 52m

$241

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Mon 10/27

5:00 pm-11:13 am

2 stops19h 13m

Winnipeg

Mon 11/3

12:20 pm-8:22 pm

1 stop7h 02m

$243

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Mon 11/17

9:15 pm-11:35 am

1 stop15h 20m

Winnipeg

Sun 11/23

8:05 pm-10:24 am

1 stop13h 19m

$252

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sun 9/28

10:59 am-10:33 pm

1 stop12h 34m

Winnipeg

Sun 10/5

2:20 pm-11:58 am

2 stops20h 38m

$254

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 10/11

7:15 am-10:33 pm

1 stop16h 18m

Winnipeg

Sat 10/18

7:00 am-10:07 pm

2 stops14h 07m

$254

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/21

8:50 am-3:30 pm

1 stop7h 40m

Winnipeg

Wed 11/26

12:20 pm-8:22 pm

1 stop7h 02m

$261

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 11/21

7:05 pm-11:57 am

2 stops17h 52m

Winnipeg

Wed 11/26

8:40 am-7:36 pm

1 stop9h 56m

$265

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 3/10

7:35 pm-11:39 am

1 stop17h 04m

Winnipeg

Wed 3/11

2:15 pm-12:24 am

2 stops9h 09m

$265

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Mon 11/17

10:07 am-10:41 pm

2 stops13h 34m

Winnipeg

Sun 11/23

12:10 pm-11:20 pm

1 stop10h 10m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 results
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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, August is the cheapest month in which you can book a flight from Kissimmee to Winnipeg (average of $358). Flying from Kissimmee to Winnipeg in December is currently the most expensive (average of $501). 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 September 15, 2025.

When flying from Kissimmee to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 15, 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
8.0
Very good
7,956 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
8.0
Very good
7,956 reviews
Delta
8.0
Very good
7,956 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
8,931 reviews
Delta
8.0
Very good
7,956 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
3,091 reviews
Delta
8.0
Very good
7,956 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

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
10,000 reviews
Delta
8.0
Very good
7,956 reviews

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

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. WestJet provides one of the quickest options available for as low as $241. 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: Delta (78%), WestJet (78%), Aeromexico( 78%).

  • 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, August is the cheapest month in which you can book a flight from Kissimmee to Winnipeg (average of $358). Flying from Kissimmee to Winnipeg in December is currently the most expensive (average of $501). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$483FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$149Average$450FlexibilityNo cancel feeOn-time67%
WestJetCheapest$198Average$339FlexibilityNo cancel feeOn-time60%
DeltaCheapest$229Average$486FlexibilityNo cancel feeOn-timeN/A

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