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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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
5 Aug — 12 Aug1
1 adult

Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or May, booked 33 days in advance, depart on a Wednesday or Sunday 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 31 July 2025.

Round-trip from

C$ 317

One-way from

C$ 155

Popular in

December

Cheapest in

October

Average price

C$ 466
WestJet
  • WestJet
  • 13/9-20/9
  • Nonstop
  • 8h 17m total
  • Winnipeg to Kissimmee
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Porter Airlines
  • Porter Airlines
  • 7/10
  • 1 total stop
  • 7h 21m total
  • Winnipeg to Kissimmee
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Winnipeg to Kissimmee

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 31 July 2025.

Sat 13/99:10 a.m.YWG - MCO
Nonstop4h 00mWestJet
Sat 20/93:15 p.m.MCO - YWG
Nonstop4h 17mWestJet
Deal found 31/7C$ 317
Tue 2/128:15 a.m.YWG - MCO
1 stop7h 52mAir Canada
Tue 9/128:30 a.m.MCO - YWG
1 stop9h 05mAir Canada
Deal found 30/7C$ 328
Tue 2/122:20 p.m.YWG - MCO
2 stops9h 24mUnited Airlines
Tue 9/129:25 a.m.MCO - YWG
2 stops12h 30mUnited Airlines
Deal found 28/7C$ 336
Wed 15/1011:20 a.m.YWG - MCO
1 stop7h 21mMultiple Airlines
Wed 29/106:00 a.m.MCO - YWG
1 stop10h 07mMultiple Airlines
Deal found 29/7C$ 342
Fri 31/106:00 a.m.YWG - MCO
1 stop7h 00mPorter Airlines
Fri 5/123:00 p.m.MCO - YWG
1 stop9h 35mPorter Airlines
Deal found 29/7C$ 357

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 31 July 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

Sat 13/9

9:10 a.m.-2:10 p.m.

Nonstop4h 00m

Orlando

Sat 20/9

3:15 p.m.-6:32 p.m.

Nonstop4h 17m

C$ 317

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 2/12

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

1 stop7h 52m

Orlando

Tue 9/12

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

1 stop9h 05m

C$ 328

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 2/12

2:20 p.m.-12:44 a.m.

2 stops9h 24m

Orlando

Tue 9/12

9:25 a.m.-8:55 p.m.

2 stops12h 30m

C$ 336

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Wed 15/10

11:20 a.m.-7:41 p.m.

1 stop7h 21m

Orlando

Wed 29/10

6:00 a.m.-3:07 p.m.

1 stop10h 07m

C$ 342

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 31/10

6:00 a.m.-2:00 p.m.

1 stop7h 00m

Orlando

Fri 5/12

3:00 p.m.-11:35 p.m.

1 stop9h 35m

C$ 357

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 7/10

11:20 a.m.-7:41 p.m.

1 stop7h 21m

C$ 155

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 11/10

9:10 a.m.-2:10 p.m.

Nonstop4h 00m

C$ 195

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Thu 18/9

7:00 a.m.-7:51 p.m.

2 stops11h 51m

C$ 206

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Fri 15/8

9:00 a.m.-12:11 p.m.

1 stop26h 11m

C$ 250

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Thu 18/9

8:10 p.m.-4:30 p.m.

2 stops19h 20m

C$ 257

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/7

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 25 July 2025.

The best time to book flights from Winnipeg to Kissimmee is 33 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$ 311). 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 31 July 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 27 July 2025.

Travelers seeking maximum savings on their Winnipeg to Kissimmee flight should consider departing on Sunday 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 31 July 2025.
Check out reviews from past customers who have flown with Porter Airlines,United Airlines, andWestJet 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
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,851 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Overall

8.0

Crew

8.7

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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.

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

    C$ 155 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$ 195 and C$ 206, 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 (67%), WestJet (50%) or Aeromexico (50%) 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$ 207. On average you can expect to pay C$ 320. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 260.

  • 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$ 311). 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

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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 31 July 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 220AverageC$ 408FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 271AverageC$ 465FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
DeltaCheapestC$ 274AverageC$ 555FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 282AverageC$ 587FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 310AverageC$ 555FlexibilityNo 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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