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Cheap flights from Winnipeg to Kissimmee from C$ 155

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 14/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
3 Apr — 10 Apr1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or September, booked 69 days in advance, depart on a Saturday or Monday and return on a Tuesday

Cheap 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 4 March 2026.

Sun 12/47:30 a.m.
YWG
-
MCO
1 stop13h 02m
Multiple Airlines
Fri 17/46:22 a.m.
MCO
-
YWG
1 stop9h 47m
Multiple Airlines
Deal found 27/2C$ 328
Sun 12/48:45 a.m.
YWG
-
MCO
1 stop13h 50m
United Airlines
Fri 17/47:40 p.m.
MCO
-
YWG
1 stop17h 12m
United Airlines
Deal found 1/3C$ 354
Tue 14/48:00 a.m.
YWG
-
MCO
Nonstop4h 03m
Multiple Airlines
Fri 17/45:10 a.m.
MCO
-
YWG
1 stop10h 59m
Multiple Airlines
Deal found 1/3C$ 358
Sun 5/42:00 p.m.
YWG
-
MCO
1 stop6h 58m
United Airlines
Fri 17/47:40 p.m.
MCO
-
YWG
1 stop17h 12m
United Airlines
Deal found 3/3C$ 378
Sun 19/47:30 a.m.
YWG
-
MCO
1 stop14h 59m
Multiple Airlines
Fri 24/46:22 a.m.
MCO
-
YWG
1 stop9h 47m
Multiple Airlines
Deal found 4/3C$ 379
Tue 31/38:45 a.m.
YWG
-
MCO
1 stop13h 52m
United Airlines
Tue 7/45:03 p.m.
MCO
-
YWG
2 stops19h 49m
United Airlines
Deal found 3/3C$ 384
Fri 3/48:45 a.m.
YWG
-
MCO
1 stop13h 50m
United Airlines
Fri 10/47:01 p.m.
MCO
-
YWG
2 stops17h 51m
United Airlines
Deal found 2/3C$ 386
Fri 10/45:20 p.m.
YWG
-
MCO
1 stop6h 13m
Delta
Fri 17/46:53 a.m.
MCO
-
YWG
1 stop10h 29m
Delta
Deal found 2/3C$ 394
Tue 31/311:55 a.m.
YWG
-
MCO
1 stop9h 32m
Delta
Wed 13/56:05 a.m.
MCO
-
YWG
1 stop10h 15m
Delta
Deal found 28/2C$ 404

Find flight deals from Winnipeg to Kissimmee

Keep the following information in mind while searching for Winnipeg to Kissimmee flight deals. Data was last updated 4 March 2026.

Round-trip from

C$ 328

One-way from

C$ 155

Popular in

February

Cheapest in

October

Average price

C$ 561
12/4-17/4
  • 12/4-17/4
  • 2 total stops
  • 22h 49m total
  • Winnipeg to Kissimmee
Search Deals
WestJet
  • WestJet
  • 14/4
  • Nonstop
  • 4h 03m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 27 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 4 March 2026.
Use the filters below to find and compare flights from Winnipeg to Kissimmee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 5/5

2:00 p.m.-9:55 p.m.

1 stop6h 55m

Orlando

Tue 12/5

3:05 p.m.-11:52 a.m.

2 stops21h 47m

C$ 364

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 17/4

8:45 a.m.-9:48 a.m.

2 stops24h 03m

Orlando

Fri 24/4

6:54 p.m.-11:52 a.m.

2 stops17h 58m

C$ 364

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 12/4

8:45 a.m.-11:20 a.m.

2 stops25h 35m

Orlando

Fri 17/4

7:01 p.m.-11:52 a.m.

2 stops17h 51m

C$ 364

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 19/4

8:45 a.m.-10:46 a.m.

2 stops25h 01m

Orlando

Fri 24/4

7:01 p.m.-11:52 a.m.

2 stops17h 51m

C$ 384

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 5/4

2:00 p.m.-10:46 a.m.

2 stops19h 46m

Orlando

Fri 17/4

7:01 p.m.-11:52 a.m.

2 stops17h 51m

C$ 384

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 31/3

11:55 a.m.-10:27 p.m.

1 stop9h 32m

Orlando

Wed 13/5

6:05 a.m.-3:20 p.m.

1 stop10h 15m

C$ 404

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 12/4

7:30 a.m.-6:40 p.m.

1 stop10h 10m

Orlando

Fri 17/4

10:00 p.m.-1:26 a.m.

Nonstop4h 26m

C$ 441

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 14/4

7:05 a.m.-12:45 a.m.

2 stops16h 40m

Orlando

Tue 21/4

7:00 a.m.-8:57 p.m.

2 stops14h 57m

C$ 471

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 3/4

11:55 a.m.-10:27 p.m.

1 stop9h 32m

Orlando

Sat 11/4

2:03 p.m.-11:35 p.m.

1 stop10h 32m

C$ 475

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Mon 6/4

8:00 a.m.-7:54 a.m.

1 stop22h 54m

C$ 196

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/3

Showing 1-10 of 18 resultsSorted by cheapest first
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 27 February 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$ 218). Flying from Winnipeg to Kissimmee in March is currently the most expensive (average of C$ 322). 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 4 March 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 4 March 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
421 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
421 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Delta
7.9
Good
8,245 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
United Airlines
7.4
Good
9,382 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
WestJet
7.2
Good
3,281 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Canada
7.1
Good
10,775 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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 6h 55m. United Airlines provides one of the quickest options available for as low as C$ 364. The distance between Winnipeg and Kissimmee is about 2739 km.

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

    C$ 145 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 Delta, with prices starting from C$ 154 and C$ 212, 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 (75%), Delta (59%) or WestJet (59%) 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$ 163. On average you can expect to pay C$ 510. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 378.

  • 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$ 218). Flying from Winnipeg to Kissimmee in March is currently the most expensive (average of C$ 322). 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 4 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 198AverageC$ 412FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 242AverageC$ 460FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 252AverageC$ 484FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 282AverageC$ 599FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 303AverageC$ 435FlexibilityNo 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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