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Cheap flights from Winnipeg to Kissimmee from C$ 163

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 18/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
4 Nov — 11 Nov1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or September, booked 44 days in advance, depart on a Monday or Saturday and return on a Thursday

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 5 October 2025.

Round-trip from

C$ 264

One-way from

C$ 163

Popular in

December

Cheapest in

October

Average price

C$ 343
WestJet
  • WestJet
  • 25/10-7/11
  • Nonstop
  • 8h 26m total
  • Winnipeg to Kissimmee
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Porter Airlines
  • Porter Airlines
  • 18/10
  • 1 total stop
  • 7h 21m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (C$ 48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Find flight deals from Winnipeg to Kissimmee

Enter your travel dates to find the best prices.

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 5 October 2025.

Sat 25/109:10 a.m.YWG - MCO
Nonstop4h 00mWestJet
Fri 7/1110:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 3/10C$ 264
Sat 25/109:10 a.m.YWG - MCO
Nonstop4h 00mWestJet
Tue 4/112:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 3/10C$ 265
Fri 31/104:00 p.m.YWG - MCO
Nonstop4h 03mWestJet
Fri 7/1110:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 3/10C$ 268
Fri 31/104:00 p.m.YWG - MCO
Nonstop4h 03mWestJet
Fri 5/1210:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 3/10C$ 282
Tue 28/108:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
Tue 4/112:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 3/10C$ 286
Sat 25/109:10 a.m.YWG - MCO
Nonstop4h 00mMultiple Airlines
Wed 5/119:00 p.m.MCO - YWG
2 stops28h 41mMultiple Airlines
Deal found 3/10C$ 290
Tue 28/108:00 a.m.YWG - MCO
Nonstop4h 07mMultiple Airlines
Tue 4/119:00 p.m.MCO - YWG
2 stops22h 06mMultiple Airlines
Deal found 3/10C$ 291
Sat 25/109:10 a.m.YWG - MCO
Nonstop4h 00mMultiple Airlines
Sat 8/1110:16 p.m.MCO - YWG
1 stop17h 51mMultiple Airlines
Deal found 3/10C$ 293
Tue 28/108:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
Fri 7/1111:10 a.m.MCO - YWG
1 stop9h 02mWestJet
Deal found 3/10C$ 294
Tue 28/108:00 a.m.YWG - MCO
Nonstop4h 07mMultiple Airlines
Sat 8/1110:16 p.m.MCO - YWG
1 stop17h 51mMultiple Airlines
Deal found 3/10C$ 296

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 5 October 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

Fri 9/1

2:20 p.m.-12:45 a.m.

2 stops9h 25m

Orlando

Fri 16/1

8:30 a.m.-4:35 p.m.

1 stop9h 05m

C$ 314

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 3/3

2:20 p.m.-10:57 a.m.

2 stops19h 37m

Orlando

Wed 4/3

8:43 p.m.-11:39 a.m.

1 stop15h 56m

C$ 318

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 27/1

8:15 a.m.-5:07 p.m.

1 stop7h 52m

Orlando

Tue 3/2

8:30 a.m.-4:35 p.m.

1 stop9h 05m

C$ 330

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 21/2

12:20 p.m.-8:16 p.m.

1 stop6h 56m

Orlando

Sat 28/2

8:30 a.m.-3:30 p.m.

1 stop8h 00m

C$ 335

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 27/1

2:20 p.m.-12:45 a.m.

2 stops9h 25m

Orlando

Tue 3/2

7:35 p.m.-11:57 a.m.

1 stop17h 22m

C$ 339

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 3/3

2:20 p.m.-12:43 a.m.

2 stops9h 23m

Orlando

Tue 10/3

7:35 p.m.-11:39 a.m.

1 stop17h 04m

C$ 339

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 16/12

8:15 a.m.-5:07 p.m.

1 stop7h 52m

Orlando

Fri 26/12

8:30 a.m.-4:35 p.m.

1 stop9h 05m

C$ 347

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 31/10

4:00 p.m.-9:03 p.m.

Nonstop4h 03m

Orlando

Tue 2/12

11:10 a.m.-7:12 p.m.

1 stop9h 02m

C$ 350

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 9/1

2:20 p.m.-10:50 a.m.

2 stops19h 30m

Orlando

Fri 16/1

4:53 p.m.-11:57 a.m.

2 stops20h 04m

C$ 356

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 21/2

1:45 p.m.-11:02 p.m.

1 stop8h 17m

Orlando

Tue 24/2

8:30 a.m.-4:35 p.m.

1 stop9h 05m

C$ 357

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/10

Showing 1-10 of 20 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 3 October 2025.

The best time to book flights from Winnipeg to Kissimmee is 44 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$ 312). 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 5 October 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 28 September 2025.

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

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 5 October 2025.
Check out reviews from past customers who have flown with Delta,Porter Airlines, andUnited Airlines from Winnipeg to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,970 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
7,970 reviews
Delta
8.0
Very good
7,970 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
374 reviews
Delta
8.0
Very good
7,970 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
8,953 reviews
Delta
8.0
Very good
7,970 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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
3,114 reviews
Delta
8.0
Very good
7,970 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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 Canada
7.1
Good
10,236 reviews
Delta
8.0
Very good
7,970 reviews
Check prices

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

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.

  • How long is the flight from Winnipeg to Kissimmee?

    A quick flight from Winnipeg to Kissimmee can take about 7h 52m. United Airlines provides one of the quickest options available for as low as C$ 330. The distance between Winnipeg and Kissimmee is about 2739 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    C$ 163 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on WestJet and Air Canada, with prices starting from C$ 169 and C$ 187, 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 Delta (94%), WestJet (89%) or Aeromexico (89%) 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$ 157. On average you can expect to pay C$ 505. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 280.

  • 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$ 312). 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 5 October 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 221AverageC$ 432FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 255AverageC$ 454FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 260AverageC$ 542FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 264AverageC$ 541FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 308AverageC$ 531FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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