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Cheap flights from Winnipeg to Kissimmee from C$ 234

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
18 May — 25 May1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or September, booked 37 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 18 April 2026.

Wed 3/69:05 p.m.
YWG
-
MCO
2 stops12h 35m
WestJet
Wed 10/65:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 15/4C$ 453
Tue 2/611:55 a.m.
YWG
-
MCO
1 stop6h 56m
Delta
Tue 9/67:00 a.m.
MCO
-
YWG
1 stop10h 52m
Delta
Deal found 18/4C$ 454
Wed 1/77:45 a.m.
YWG
-
MCO
1 stop25h 55m
WestJet
Fri 10/75:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 13/4C$ 465
Sun 21/610:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Sun 28/65:05 p.m.
MCO
-
YWG
1 stop28h 15m
WestJet
Deal found 17/4C$ 468
Fri 29/56:40 a.m.
YWG
-
MCO
1 stop9h 24m
Delta
Wed 22/76:24 p.m.
MCO
-
YWG
1 stop6h 06m
Delta
Deal found 17/4C$ 469
Sun 7/66:05 p.m.
YWG
-
MCO
1 stop15h 35m
WestJet
Wed 10/65:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 17/4C$ 472
Sat 11/74:25 p.m.
YWG
-
MCO
1 stop17h 15m
WestJet
Fri 17/75:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 17/4C$ 476
Sun 10/56:05 p.m.
YWG
-
MCO
1 stop24h 40m
WestJet
Wed 13/58:35 p.m.
MCO
-
YWG
1 stop14h 10m
WestJet
Deal found 17/4C$ 482
Fri 29/56:15 a.m.
YWG
-
MCO
1 stop12h 30m
WestJet
Fri 5/65:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 14/4C$ 483
Wed 3/66:15 a.m.
YWG
-
MCO
1 stop27h 25m
WestJet
Mon 8/65:05 p.m.
MCO
-
YWG
1 stop17h 40m
WestJet
Deal found 15/4C$ 484

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 18 April 2026.

Round-trip from

C$ 453

One-way from

C$ 234

Popular in

February

Cheapest in

October

Average price

C$ 424
WestJet
  • WestJet
  • 3/6-10/6
  • 3 total stops
  • 21h 25m total
  • Winnipeg to Kissimmee
Search Deals
29/5
  • 29/5
  • 3 total stops
  • 23h 23m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 103 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 18 April 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

Tue 2/6

11:55 a.m.-7:51 p.m.

1 stop6h 56m

Orlando

Tue 9/6

7:00 a.m.-4:52 p.m.

1 stop10h 52m

C$ 454

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 1/7

10:45 a.m.-10:40 a.m.

1 stop22h 55m

Orlando

Fri 10/7

11:20 a.m.-7:49 p.m.

2 stops9h 29m

C$ 539

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 27/6

8:00 a.m.-7:45 p.m.

2 stops34h 45m

Orlando

Sat 4/7

8:35 p.m.-9:45 a.m.

1 stop14h 10m

C$ 571

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 22/7

12:46 p.m.-11:58 p.m.

1 stop10h 12m

Orlando

Sat 1/8

7:00 a.m.-4:52 p.m.

1 stop10h 52m

C$ 572

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 25/7

5:42 p.m.-11:58 p.m.

1 stop5h 16m

Orlando

Mon 3/8

7:00 a.m.-3:08 p.m.

1 stop9h 08m

C$ 609

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 25/7

5:42 p.m.-11:58 p.m.

1 stop5h 16m

Orlando

Sun 2/8

7:00 a.m.-4:52 p.m.

1 stop10h 52m

C$ 609

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 1/7

8:00 a.m.-10:40 a.m.

2 stops25h 40m

Orlando

Fri 10/7

8:35 p.m.-2:05 p.m.

2 stops18h 30m

C$ 617

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 10/6

3:54 p.m.-11:57 p.m.

1 stop7h 03m

Orlando

Sat 13/6

7:00 a.m.-3:19 p.m.

1 stop9h 19m

C$ 636

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 22/7

12:46 p.m.-11:58 p.m.

1 stop10h 12m

Orlando

Fri 31/7

10:05 a.m.-11:30 p.m.

2 stops14h 25m

C$ 654

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 2/10

6:00 a.m.-7:45 p.m.

2 stops12h 45m

Orlando

Mon 5/10

5:05 p.m.-2:05 p.m.

2 stops22h 00m

C$ 658

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/4

Showing 1-10 of 20 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 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 10 April 2026.

The best time to book flights from Winnipeg to Kissimmee is 37 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 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 18 April 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.

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

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 18 April 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
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Delta
7.9
Good
8,422 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,605 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,321 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,939 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 56m. Delta provides one of the quickest options available for as low as C$ 454. 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$ 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$ 213, 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 (77%) or WestJet (77%) 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$ 230. On average you can expect to pay C$ 770. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 469.

  • 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 18 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 210AverageC$ 424FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 255AverageC$ 469FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 271AverageC$ 521FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 282AverageC$ 598FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 311AverageC$ 457FlexibilityNo 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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