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$109+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Kissimmee to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Kissimmee (K1S) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$279
(Trip.com)

One-way from

$109
(Trip.com)

Popular in

May

Cheapest in

December

Average price

$386
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. 9% potential increase in price ($52 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 January 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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 5/129:00 pmMCO - YWG
1 stop13h 43mWestJet
Sun 5/182:35 pmYWG - MCO
1 stop7h 20mWestJet
Deal found 1/20$258
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 5/155:35 amMCO - YWG
1 stop11h 53mMultiple Airlines
Sun 5/182:35 pmYWG - MCO
1 stop7h 20mMultiple Airlines
Deal found 1/20$277
This Delta deal was found by Cheapflights users on 1/20. 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.
Wed 5/142:25 pmMCO - YWG
1 stop9h 58mDelta
Sun 5/1812:40 pmYWG - MCO
1 stop10h 21mDelta
Deal found 1/20$318
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Tue 5/137:15 amMCO - YWG
2 stops14h 52mUnited Airlines
Wed 5/212:20 pmYWG - MCO
1 stop6h 21mUnited Airlines
Deal found 1/20$319
This Air Canada deal was found by Cheapflights users on 1/20. 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 5/148:15 pmMCO - YWG
1 stop14h 37mAir Canada
Tue 5/208:00 amYWG - MCO
1 stop7h 37mAir Canada
Deal found 1/20$322
This FlightHub deal was found by Cheapflights users on 1/21. 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 3/78:45 amMCO - YWG
2 stops10h 14mPorter Airlines
Sat 3/1511:35 amYWG - MCO
1 stop7h 09mPorter Airlines
Deal found 1/21$414

Find flights from Kissimmee to Winnipeg within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Mon 5/12

9:00 pm-9:43 am

1 stop13h 43m

Winnipeg

Sun 5/18

2:35 pm-10:55 pm

1 stop7h 20m

$258

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 5/15

5:35 am-4:28 pm

1 stop11h 53m

Winnipeg

Sun 5/18

2:35 pm-10:55 pm

1 stop7h 20m

$277

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 5/14

2:25 pm-11:23 pm

1 stop9h 58m

Winnipeg

Sun 5/18

12:40 pm-12:01 am

1 stop10h 21m

$318

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 5/13

7:15 am-9:07 pm

2 stops14h 52m

Winnipeg

Wed 5/21

2:20 pm-9:41 pm

1 stop6h 21m

$319

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 5/14

8:15 pm-9:52 am

1 stop14h 37m

Winnipeg

Tue 5/20

8:00 am-4:37 pm

1 stop7h 37m

$322

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 3/7

8:45 am-5:59 pm

2 stops10h 14m

Winnipeg

Sat 3/15

11:35 am-7:44 pm

1 stop7h 09m

$414

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Wed 2/26

6:00 am-3:08 pm

1 stop10h 08m

$111

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 4/17

1:15 pm-4:41 pm

Nonstop4h 26m

$135

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sun 3/16

8:51 pm-1:27 pm

1 stop17h 36m

$138

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 4/1

11:20 am-7:45 pm

1 stop9h 25m

$144

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

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.

Travel insights for flights from Kissimmee to Winnipeg

Get recent, data-driven insights about flights from Kissimmee to Winnipeg including ideal travel times, pricing trends, and more.

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 February is currently the most expensive (average of $521). 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 January 21, 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 January 21, 2025.
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
8,985 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Air Canada
7.0
Good
8,635 reviews
Delta
8.0
Very good
8,521 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 WestJet, which is currently one of the cheapest options available, starting at $128. United Airlines flights start at $138 while deals on Air Canada start at $144 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: WestJet (60%), Delta (44%), Aeromexico( 25%).

  • What are the cheapest flights from Kissimmee to Winnipeg?

    Looking at all options, your cheapest flight can be booked for $149. While the most popular route (Orlando - Winnipeg) can be booked for $222 on average our data indicates $255 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 February is currently the most expensive (average of $521). 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 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$157Average$485FlexibilityNo cancel feeOn-time67%
WestJetCheapest$198Average$433FlexibilityNo cancel feeOn-time60%
DeltaCheapest$309Average$595FlexibilityNo cancel feeOn-timeN/A
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