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$110+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$234
(Kiwi.com)

One-way from

$110
(Air Canada)

Popular in

April

Cheapest in

October

Average price

$624
Provider with most accurate pricing for Orlando (ORL)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Winnipeg flights.
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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. 11% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Sat 5/313:15 pmMCO - YWG
Nonstop4h 24mMultiple Airlines
Mon 6/211:25 amYWG - MCO
1 stop7h 16mMultiple Airlines
Deal found 4/29$234
This Trip.com deal was found by Cheapflights users on 5/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/141:45 pmMCO - YWG
1 stop10h 01mPorter Airlines
Sat 6/2111:45 amYWG - MCO
1 stop6h 56mPorter Airlines
Deal found 5/1$303
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 5/283:43 pmMCO - YWG
2 stops22h 26mUnited Airlines
Fri 5/307:00 amYWG - MCO
1 stop6h 56mUnited Airlines
Deal found 4/30$314
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/143:15 pmMCO - YWG
Nonstop4h 24mDelta
Sat 6/219:10 amYWG - MCO
Nonstop4h 00mDelta
Deal found 5/1$450
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2911:00 amMCO - YWG
2 stops11h 28mWestJet
Mon 6/26:15 pmYWG - MCO
2 stops14h 54mWestJet
Deal found 4/29$550
This Air Canada deal was found by Cheapflights users on 5/1. 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.
Fri 10/318:25 amMCO - YWG
2 stops12h 33mAir Canada
Tue 11/118:00 amYWG - MCO
1 stop8h 08mAir Canada
Deal found 5/1$784

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 May 1, 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

Sat 5/31

3:15 pm-6:39 pm

Nonstop4h 24m

Winnipeg

Mon 6/2

11:25 am-7:41 pm

1 stop7h 16m

$234

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 6/14

1:45 pm-10:46 pm

1 stop10h 01m

Winnipeg

Sat 6/21

11:45 am-7:41 pm

1 stop6h 56m

$303

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 5/28

3:43 pm-1:09 pm

2 stops22h 26m

Winnipeg

Fri 5/30

7:00 am-2:56 pm

1 stop6h 56m

$314

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 6/14

3:15 pm-6:39 pm

Nonstop4h 24m

Winnipeg

Sat 6/21

9:10 am-2:10 pm

Nonstop4h 00m

$450

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 5/29

11:00 am-9:28 pm

2 stops11h 28m

Winnipeg

Mon 6/2

6:15 pm-10:09 am

2 stops14h 54m

$550

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 5/28

12:16 pm-10:33 pm

1 stop11h 17m

$110

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 5/24

3:15 pm-6:39 pm

Nonstop4h 24m

$117

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 5/21

6:40 am-11:57 am

1 stop6h 17m

$121

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 5/14

10:17 pm-4:28 pm

1 stop19h 11m

$127

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 5/22

8:58 pm-1:09 pm

1 stop17h 11m

$128

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 $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 May 1, 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.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

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 May 1, 2025.
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Food

7.6

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Porter Airlines
8.0
Very good
285 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Food

7.6

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Delta
8.0
Very good
7,934 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Food

7.6

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
United Airlines
7.4
Good
8,696 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Food

7.6

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
WestJet
7.2
Good
2,826 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Food

7.6

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you
Air Canada
7.0
Good
9,252 reviews
Porter Airlines
8.0
Very good
285 reviews

Comfort

8.1

Boarding

8.2

Entertainment

7.0

Food

7.6

Crew

8.8

Overall

8.0

Reviews

1 / 18
10.0
Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

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 3 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 Air Canada, which is currently one of the cheapest options available, starting at $110. WestJet flights start at $117 while deals on Delta start at $121 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 (74%), WestJet (68%), Aeromexico( 25%).

  • 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 $234 on average our data indicates $465 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 $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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Kissimmee to Winnipeg

Discover the top 3 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$149Average$450FlexibilityNo cancel feeOn-time67%
WestJetCheapest$198Average$395FlexibilityNo cancel feeOn-time60%
DeltaCheapest$309Average$605FlexibilityNo cancel feeOn-timeN/A

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