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Cheap flights from Winnipeg to Kissimmee from C$ 194

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 29/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
7 Apr — 14 Apr1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or April, booked 69 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

Cheap flight deals from Winnipeg to Kissimmee

Keep the following information in mind while searching for Winnipeg to Kissimmee flight deals. Data was last updated 2 April 2025.

Round-trip from

C$ 319

One-way from

C$ 194

Popular in

December

Cheapest in

October

Average price

C$ 493
United Airlines
  • United Airlines
  • 8/5-14/5
  • 2 total stops
  • 21h 32m total
  • Winnipeg to Kissimmee
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29/4
  • 29/4
  • 1 total stop
  • 13h 48m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (C$ 14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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Find flight deals from Winnipeg to Kissimmee

Cheapest flights from Winnipeg to Kissimmee
Explore the most affordable flight options available from Winnipeg to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 2 April 2025.

Thu 8/54:25 p.m.YWG - MCO
1 stop12h 16mUnited Airlines
Wed 14/57:15 a.m.MCO - YWG
1 stop9h 16mUnited Airlines
Deal found 1/4C$ 319
Sat 31/511:25 a.m.YWG - MCO
1 stop7h 16mMultiple Airlines
Sat 7/63:15 p.m.MCO - YWG
Nonstop4h 24mMultiple Airlines
Deal found 1/4C$ 343
Sun 1/611:25 a.m.YWG - MCO
1 stop7h 16mPorter Airlines
Sat 7/61:45 p.m.MCO - YWG
1 stop10h 01mPorter Airlines
Deal found 1/4C$ 345
Mon 15/910:45 a.m.YWG - MCO
1 stop7h 10mWestJet
Mon 22/911:00 a.m.MCO - YWG
1 stop6h 58mWestJet
Deal found 2/4C$ 353
Tue 21/108:00 a.m.YWG - MCO
1 stop7h 37mAir Canada
Tue 28/108:25 a.m.MCO - YWG
1 stop7h 48mAir Canada
Deal found 1/4C$ 368
Sat 24/59:10 a.m.YWG - MCO
Nonstop4h 00mDelta
Sat 31/53:15 p.m.MCO - YWG
Nonstop4h 24mDelta
Deal found 1/4C$ 461
Wed 25/66:55 p.m.YWG - MCO
2 stops14h 10mAir Transat
Sun 29/69:05 p.m.MCO - YWG
2 stops14h 45mAir Transat
Deal found 2/4C$ 761

Cheapflights Fare Finder

Customize your flight search to find flights from Winnipeg to Kissimmee 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 629,999 searches. Data last updated 2 April 2025.
Use the filters below to find and compare flights from Winnipeg to Kissimmee that are best for you.

Fly from

Winnipeg

Fly to

Kissimmee

Route

Depart

Return

Price

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Thu 8/5

4:25 p.m.-5:41 a.m.

1 stop12h 16m

Orlando

Wed 14/5

7:15 a.m.-3:31 p.m.

1 stop9h 16m

C$ 319

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 31/5

11:25 a.m.-7:41 p.m.

1 stop7h 16m

Orlando

Sat 7/6

3:15 p.m.-6:39 p.m.

Nonstop4h 24m

C$ 343

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 1/6

11:25 a.m.-7:41 p.m.

1 stop7h 16m

Orlando

Sat 7/6

1:45 p.m.-10:46 p.m.

1 stop10h 01m

C$ 345

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Mon 15/9

10:45 a.m.-6:55 p.m.

1 stop7h 10m

Orlando

Mon 22/9

11:00 a.m.-4:58 p.m.

1 stop6h 58m

C$ 353

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 21/9

8:00 a.m.-4:37 p.m.

1 stop7h 37m

Orlando

Sat 27/9

7:00 a.m.-4:10 p.m.

1 stop10h 10m

C$ 401

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 24/5

9:10 a.m.-2:10 p.m.

Nonstop4h 00m

Orlando

Sat 31/5

3:15 p.m.-6:39 p.m.

Nonstop4h 24m

C$ 461

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 25/6

6:55 p.m.-10:05 a.m.

2 stops14h 10m

Orlando

Sun 29/6

9:05 p.m.-10:50 a.m.

2 stops14h 45m

C$ 750

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 29/4

9:00 a.m.-11:48 p.m.

1 stop13h 48m

C$ 194

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 24/5

7:00 a.m.-9:46 p.m.

1 stop13h 46m

C$ 202

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 25/4

4:00 p.m.-9:00 p.m.

Nonstop4h 00m

C$ 266

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 11 results
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Best time to book a flight from Winnipeg to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Winnipeg 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 Winnipeg to Kissimmee

How far ahead should I book a flight from Winnipeg to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Kissimmee. Price data was last updated on 28 March 2025.

The best time to book flights from Winnipeg to Kissimmee is 69 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Winnipeg to Kissimmee?

Currently, June is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 196). Flying from Winnipeg to Kissimmee in February is currently the most expensive (average of C$ 316). 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 YWG to K1S?

Find hourly flight availability from Winnipeg to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 2 April 2025.

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

What is the cheapest day to fly from Winnipeg to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Kissimmee. Price data was last updated on 30 March 2025.

Travelers seeking maximum savings on their Winnipeg to Kissimmee flight should consider departing on Sunday mornings when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Kissimmee by month

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

In terms of precipitation, rainfall in Kissimmee ranges from 61.0 - 221.0 mm per month. June is typically the wettest month, when rainfall can reach 221.0 mm. November is typically the driest time to visit Kissimmee when rainfall is around 61.0 mm.

Temperature in Kissimmee by month

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

If weather is an important factor for your trip to Kissimmee, 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 29.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 16.0 C).

Reviews of airlines servicing Kissimmee

Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated 2 April 2025.
See what other customers who have flown with Delta, Porter Airlines and Air Transat from Winnipeg to Kissimmee have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Richard,Sep 2023

YYZ - ATL

Four hour delay (missing two screws). Seats in need of repair.
Delta
8.0
Very good
7,898 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Richard,Sep 2023

YYZ - ATL

Four hour delay (missing two screws). Seats in need of repair.
Porter Airlines
7.9
Good
279 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Richard,Sep 2023

YYZ - ATL

Four hour delay (missing two screws). Seats in need of repair.
Air Transat
7.8
Good
381 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Richard,Sep 2023

YYZ - ATL

Four hour delay (missing two screws). Seats in need of repair.
United Airlines
7.4
Good
8,616 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Richard,Sep 2023

YYZ - ATL

Four hour delay (missing two screws). Seats in need of repair.
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,898 reviews
Check prices

Boarding

8.2

Food

7.3

Comfort

7.9

Entertainment

7.9

Crew

8.5

Overall

8.0

Reviews

1 / 20
4.0
Okay

Richard,Sep 2023

YYZ - ATL

Four hour delay (missing two screws). Seats in need of repair.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Kissimmee. 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 from for flights from Winnipeg to Kissimmee?

    If you book a flight to Kissimmee from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 0 flights from Winnipeg to Kissimmee per day from 5 different airlines.

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

    C$ 202 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and WestJet, with prices starting from C$ 266 and C$ 668, respectively.

  • What are the most reliable airlines from Winnipeg to Kissimmee?

    No one likes to see their flight delayed. When booking a flight from Winnipeg to Kissimmee consider choosing Aeromexico (83%), WestJet (72%) or Delta (72%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Winnipeg to Kissimmee?

    The cheapest flight price from Winnipeg to Kissimmee is C$ 265. On average you can expect to pay C$ 658. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 257.

  • Can I find deals for flights from Winnipeg to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Kissimmee.

  • Can I find deals for business class flights from Winnipeg to Kissimmee?

    Yes. Cheapflights offers flight deals from Winnipeg to Kissimmee 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 Winnipeg to Kissimmee?

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 196). Flying from Winnipeg to Kissimmee in February is currently the most expensive (average of C$ 316). 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 5 airlines flying from Winnipeg to Kissimmee

Discover the top 5 airlines that operate flights from Winnipeg to Kissimmee. 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 629,999 searches. Data last updated 2 April 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 228AverageC$ 422FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 261AverageC$ 494FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 299AverageC$ 649FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 322AverageC$ 601FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 366AverageC$ 614FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Kissimmee?

When you search for this flight from Winnipeg to Kissimmee, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Kissimmee?

Cheapflights simply makes it quick and affordable to book flights from Winnipeg to Kissimmee by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Winnipeg to Kissimmee with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Kissimmee, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Kissimmee become cheaper?

Yes! Start tracking prices for Winnipeg to Kissimmee flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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