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Cheap flights from Winnipeg to Kissimmee from C$ 157

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 24/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
14 Feb — 21 Feb1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or May, booked 69 days in advance, depart on a Monday or Saturday and return on a Wednesday

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 15 January 2026.

Round-trip from

C$ 315

One-way from

C$ 157

Popular in

February

Cheapest in

October

Average price

C$ 470
United Airlines
  • United Airlines
  • 7/3-14/3
  • 2 total stops
  • 24h 56m total
  • Winnipeg to Kissimmee
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WestJet
  • WestJet
  • 24/2
  • Nonstop
  • 4h 03m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 135 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 15 January 2026.

Sat 7/32:20 p.m.
YWG
-
MCO
1 stop8h 39m
United Airlines
Sat 14/38:40 p.m.
MCO
-
YWG
1 stop16h 17m
United Airlines
Deal found 14/1C$ 315
Tue 3/38:00 a.m.
YWG
-
MCO
Nonstop4h 03m
WestJet
Tue 10/39:15 p.m.
MCO
-
YWG
1 stop28h 20m
WestJet
Deal found 14/1C$ 318
Tue 24/28:00 a.m.
YWG
-
MCO
Nonstop4h 03m
WestJet
Fri 27/29:15 p.m.
MCO
-
YWG
1 stop15h 17m
WestJet
Deal found 13/1C$ 320
Fri 30/17:30 a.m.
YWG
-
MCO
1 stop25h 37m
Multiple Airlines
Fri 6/24:20 p.m.
MCO
-
YWG
1 stop8h 15m
Multiple Airlines
Deal found 14/1C$ 321
Sat 2/52:15 p.m.
YWG
-
MCO
2 stops9h 29m
United Airlines
Sat 9/57:01 p.m.
MCO
-
YWG
2 stops17h 38m
United Airlines
Deal found 14/1C$ 324
Sat 21/26:45 a.m.
YWG
-
MCO
1 stop8h 44m
Multiple Airlines
Fri 27/28:30 a.m.
MCO
-
YWG
1 stop8h 00m
Multiple Airlines
Deal found 13/1C$ 325
Mon 2/29:00 p.m.
YWG
-
MCO
2 stops16h 42m
Multiple Airlines
Fri 6/28:30 a.m.
MCO
-
YWG
1 stop8h 00m
Multiple Airlines
Deal found 13/1C$ 327
Wed 25/22:20 p.m.
YWG
-
MCO
2 stops9h 23m
United Airlines
Thu 26/28:43 p.m.
MCO
-
YWG
1 stop16h 14m
United Airlines
Deal found 13/1C$ 328
Tue 24/28:00 a.m.
YWG
-
MCO
Nonstop4h 03m
WestJet
Wed 25/29:15 p.m.
MCO
-
YWG
1 stop15h 17m
WestJet
Deal found 13/1C$ 329
Tue 24/28:00 a.m.
YWG
-
MCO
Nonstop4h 03m
WestJet
Mon 2/39:30 p.m.
MCO
-
YWG
1 stop15h 02m
WestJet
Deal found 13/1C$ 332

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 15 January 2026.
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

Sat 7/3

2:20 p.m.-11:59 p.m.

1 stop8h 39m

Orlando

Sat 14/3

8:40 p.m.-11:57 a.m.

1 stop16h 17m

C$ 315

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 8/5

8:30 a.m.-11:30 p.m.

1 stop14h 00m

Orlando

Fri 15/5

7:01 p.m.-11:39 a.m.

2 stops17h 38m

C$ 324

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 25/2

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

2 stops9h 23m

Orlando

Thu 26/2

8:43 p.m.-11:57 a.m.

1 stop16h 14m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 8/3

2:20 p.m.-11:59 p.m.

1 stop8h 39m

Orlando

Thu 12/3

8:40 p.m.-11:57 a.m.

1 stop16h 17m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 27/2

2:20 p.m.-10:42 a.m.

2 stops19h 22m

Orlando

Fri 6/3

6:58 p.m.-11:57 a.m.

2 stops17h 59m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 11/3

2:20 p.m.-12:33 a.m.

2 stops9h 13m

Orlando

Wed 18/3

8:40 p.m.-11:57 a.m.

1 stop16h 17m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 25/2

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

2 stops9h 23m

Orlando

Fri 27/2

8:43 p.m.-11:57 a.m.

1 stop16h 14m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 10/3

2:20 p.m.-9:40 p.m.

1 stop6h 20m

Orlando

Mon 16/3

8:40 p.m.-11:57 a.m.

1 stop16h 17m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Mon 6/4

2:00 p.m.-9:58 p.m.

1 stop6h 58m

Orlando

Mon 13/4

3:06 p.m.-11:52 a.m.

2 stops21h 46m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 3/3

2:20 p.m.-9:40 p.m.

1 stop6h 20m

Orlando

Tue 10/3

8:40 p.m.-11:57 a.m.

1 stop16h 17m

C$ 328

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/1

Showing 1-10 of 20 results
1
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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 9 January 2026.

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, May is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 221). Flying from Winnipeg to Kissimmee in July is currently the most expensive (average of C$ 306). 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 15 January 2026.

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.

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 15 January 2026.
Check out reviews from past customers who have flown with Porter Airlines,Delta, 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.
Porter Airlines
8.0
Very good
407 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
407 reviews
Porter Airlines
8.0
Very good
407 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Delta
7.9
Good
8,049 reviews
Porter Airlines
8.0
Very good
407 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,164 reviews
Porter Airlines
8.0
Very good
407 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,243 reviews
Porter Airlines
8.0
Very good
407 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,622 reviews
Porter Airlines
8.0
Very good
407 reviews
Check prices

Food

7.6

Boarding

8.2

Overall

8.0

Crew

8.6

Comfort

7.9

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 8h 39m. United Airlines provides one of the quickest options available for as low as C$ 315. The distance between Winnipeg and Kissimmee is about 2739 km.

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

    C$ 147 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 United Airlines, with prices starting from C$ 177 and C$ 195, 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 LATAM Airlines (83%), Delta (71%) or WestJet (71%) 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$ 296. On average you can expect to pay C$ 610. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 306.

  • 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, May is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 221). Flying from Winnipeg to Kissimmee in July is currently the most expensive (average of C$ 306). 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 15 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 201AverageC$ 421FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapestC$ 256AverageC$ 500FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 259AverageC$ 495FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 302AverageC$ 566FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 306AverageC$ 441FlexibilityNo cancel feeOn-time52%
Search Porter Airlines 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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