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Cheap flights from Winnipeg to Kissimmee from C$ 221

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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
23 Aug — 30 Aug1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in September or April, booked 59 days in advance, depart on a Thursday or Tuesday 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 24 July 2026.

Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Mon 21/95:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 21/7C$ 458
Tue 1/1211:05 a.m.
YWG
-
MCO
1 stop7h 48m
Air Canada
Sat 12/128:30 a.m.
MCO
-
YWG
1 stop9h 08m
Air Canada
Deal found 19/7C$ 470
Sat 26/94:25 p.m.
YWG
-
MCO
1 stop26h 20m
WestJet
Fri 2/108:35 p.m.
MCO
-
YWG
1 stop14h 10m
WestJet
Deal found 24/7C$ 473
Tue 1/97:00 a.m.
YWG
-
MCO
2 stops14h 14m
Multiple Airlines
Sun 20/98:35 p.m.
MCO
-
YWG
1 stop14h 10m
Multiple Airlines
Deal found 23/7C$ 481
Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Fri 18/911:30 a.m.
MCO
-
YWG
1 stop9h 10m
WestJet
Deal found 21/7C$ 494
Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Sun 20/98:35 p.m.
MCO
-
YWG
1 stop14h 10m
WestJet
Deal found 21/7C$ 498
Fri 11/97:55 p.m.
YWG
-
MCO
1 stop22h 50m
WestJet
Mon 14/95:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 23/7C$ 501
Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Thu 17/911:30 a.m.
MCO
-
YWG
1 stop10h 15m
WestJet
Deal found 21/7C$ 505
Thu 10/96:15 a.m.
YWG
-
MCO
1 stop27h 25m
WestJet
Sun 20/98:35 p.m.
MCO
-
YWG
1 stop14h 10m
WestJet
Deal found 20/7C$ 511
Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Sat 19/98:35 p.m.
MCO
-
YWG
1 stop14h 10m
WestJet
Deal found 21/7C$ 512
Mon 14/99:05 p.m.
YWG
-
MCO
2 stops13h 42m
Multiple Airlines
Mon 21/95:05 p.m.
MCO
-
YWG
1 stop8h 50m
Multiple Airlines
Deal found 21/7C$ 514

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 24 July 2026.

Round-trip from

C$ 458

One-way from

C$ 221

Popular in

December

Cheapest in

September

Average price

C$ 569
WestJet
  • WestJet
  • 13/9-21/9
  • 2 total stops
  • 16h 50m total
  • Winnipeg to Kissimmee
Search Deals
1/9
  • 1/9
  • 2 total stops
  • 14h 14m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 24 July 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

Cheapest round-trip

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 26/9

7:00 a.m.-10:40 a.m.

2 stops26h 40m

Orlando

Fri 2/10

11:30 a.m.-12:55 a.m.

2 stops14h 25m

C$ 536
Quickest round-trip

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 27/11

2:15 p.m.-11:39 p.m.

1 stop8h 24m

Orlando

Tue 8/12

8:30 a.m.-4:38 p.m.

1 stop9h 08m

C$ 546

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 16/9

8:50 p.m.-12:45 p.m.

1 stop14h 55m

Orlando

Tue 22/9

1:45 p.m.-8:45 p.m.

1 stop8h 00m

C$ 586

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 18/11

8:30 a.m.-11:39 p.m.

2 stops14h 09m

Orlando

Mon 30/11

8:24 p.m.-11:39 a.m.

1 stop16h 15m

C$ 595

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 16/1

11:35 a.m.-11:32 p.m.

2 stops10h 57m

Orlando

Fri 29/1

11:20 a.m.-9:57 p.m.

2 stops11h 37m

C$ 657

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 15/1

11:35 a.m.-11:32 p.m.

2 stops10h 57m

Orlando

Fri 29/1

11:20 a.m.-9:57 p.m.

2 stops11h 37m

C$ 657

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 17/11

2:15 p.m.-1:00 a.m.

2 stops9h 45m

Orlando

Sat 28/11

8:30 a.m.-4:38 p.m.

1 stop9h 08m

C$ 660

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 9/10

12:20 p.m.-12:59 a.m.

2 stops11h 39m

Orlando

Thu 15/10

6:20 p.m.-12:37 p.m.

2 stops19h 17m

C$ 686

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Thu 27/8

7:00 a.m.-12:59 a.m.

2 stops16h 59m

Orlando

Sat 5/9

7:55 p.m.-10:05 a.m.

1 stop15h 10m

C$ 695

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 29/8

7:00 a.m.-7:58 p.m.

2 stops11h 58m

Orlando

Sat 5/9

7:55 p.m.-10:05 a.m.

1 stop15h 10m

C$ 695

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/7

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 much does it cost to fly round-trip from Winnipeg to Kissimmee?

Airfare is below average for this route at the moment.
Winnipeg to Kissimmee flights typically cost between C$ 462 and C$ 774 in September.
The cheapest round-trip price found within the last 5 days was C$ 458 on WestJet (13 Sep-21 Sep).

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 24 July 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
448 reviews
Check prices

Food

7.5

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
448 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Delta
7.8
Good
8,482 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
United Airlines
7.4
Good
10,029 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
WestJet
7.2
Good
3,416 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,382 reviews
Porter Airlines
8.0
Very good
448 reviews
Check prices

Food

7.5

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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 10h 57m. WestJet provides one of the quickest options available for as low as C$ 657. 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 flights from Winnipeg to Kissimmee?

    The cheapest flight price from Winnipeg to Kissimmee is C$ 663. On average you can expect to pay C$ 663. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 481.

  • 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.

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 24 July 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 228AverageC$ 592FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 291AverageC$ 622FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 312AverageC$ 432FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 320AverageC$ 491FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
DeltaCheapestC$ 401AverageC$ 568FlexibilityNo 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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