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$114+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$218
(FlightHub)

One-way from

$114
(Mytrip)

Popular in

April

Cheapest in

October

Average price

$396
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. 4% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/2. 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 10/311:00 pmMCO - YWG
Nonstop4h 23mWestJet
Tue 11/117:00 amYWG - MCO
Nonstop4h 03mWestJet
Deal found 7/2$218
This FlightHub deal was found by Cheapflights users on 7/1. 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 10/311:00 pmMCO - YWG
Nonstop4h 23mMultiple Airlines
Tue 11/115:00 amYWG - MCO
1 stop7h 05mMultiple Airlines
Deal found 7/1$237
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/91:45 pmMCO - YWG
1 stop10h 01mPorter Airlines
Thu 7/1711:45 amYWG - MCO
1 stop6h 59mPorter Airlines
Deal found 7/2$267
This United Airlines deal was found by Cheapflights users on 7/2. 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.
Fri 10/319:50 amMCO - YWG
2 stops11h 58mUnited Airlines
Tue 11/118:30 amYWG - MCO
1 stop10h 06mUnited Airlines
Deal found 7/2$283
This Air Canada deal was found by Cheapflights users on 7/1. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/137:00 amMCO - YWG
1 stop11h 40mAir Canada
Sun 8/1712:00 pmYWG - MCO
1 stop10h 48mAir Canada
Deal found 7/1$402

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 July 3, 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 10/31

1:00 pm-4:23 pm

Nonstop4h 23m

Winnipeg

Tue 11/11

7:00 am-12:03 pm

Nonstop4h 03m

$218

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 10/31

1:00 pm-4:23 pm

Nonstop4h 23m

Winnipeg

Tue 11/11

5:00 am-1:05 pm

1 stop7h 05m

$237

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 10/31

9:50 am-8:48 pm

2 stops11h 58m

Winnipeg

Tue 11/11

8:30 am-7:36 pm

1 stop10h 06m

$283

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 8/13

7:00 am-5:40 pm

1 stop11h 40m

Winnipeg

Sun 8/17

12:00 pm-11:48 pm

1 stop10h 48m

$402

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sun 10/5

6:00 am-1:43 pm

2 stops8h 43m

Winnipeg

Sat 10/11

10:45 am-6:55 pm

1 stop7h 10m

$608

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 7/10

1:45 pm-10:46 pm

1 stop10h 01m

$114

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 8/16

9:40 pm-12:31 am

2 stops27h 51m

$130

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 7/12

9:32 am-10:33 pm

1 stop14h 01m

$138

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 8/23

3:15 pm-6:39 pm

Nonstop4h 24m

$171

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 8/23

6:55 am-11:53 am

1 stop5h 58m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 11 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 $497). 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 July 3, 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 July 3, 2025.
See what other customers who have flown with Porter Airlines, Delta, and United Airlines 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.
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,982 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,861 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,917 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,681 reviews
Porter Airlines
8.0
Very good
298 reviews

Entertainment

7.0

Crew

8.7

Food

7.7

Comfort

8.1

Boarding

8.2

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.

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

    To fly one-way, consider booking your trip with Porter Airlines, which is currently one of the cheapest options available, starting at $114. United Airlines flights start at $138 while deals on WestJet start at $171 one-way.

  • 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 (50%), WestJet (50%), Aeromexico( 50%).

  • What are the cheapest flights from Kissimmee to Winnipeg?

    Looking at all options, your cheapest flight can be booked for $113. While the most popular route (Orlando - Winnipeg) can be booked for $239 on average our data indicates $486 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, 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 $497). 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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$112Average$462FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$149Average$453FlexibilityNo cancel feeOn-time67%
WestJetCheapest$198Average$339FlexibilityNo cancel feeOn-time60%
DeltaCheapest$296Average$516FlexibilityNo cancel feeOn-timeN/A

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