C$ 165 Find Cheap Flights from Winnipeg to Kissimmee

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Kissimmee departing on 21/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 310
Overall average: C$ 544
Porter Airlines
Tue 24/2Tue 3/3
YWG - MCO • 1 stop
Cheapest direct flights
C$ 533
Typical prices: C$ 352-C$ 761
WestJet
Tue 20/1Tue 27/1
YWG - MCO • Direct
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Winnipeg to Kissimmee (YWG-MCO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Winnipeg to Kissimmee that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Winnipeg to Kissimmee

Tue, 24 Feb - Tue, 3 Mar
Porter Airlines Logo
12:10 p.m. - 11:25 p.m.
YWG
-
MCO
10h 15m1 stop
Porter Airlines Logo
8:30 a.m. - 3:30 p.m.
MCO
-
YWG
8h 00m1 stop
C$ 310Porter Airlines
Wed, 25 Feb - Wed, 4 Mar
Porter Airlines Logo
12:10 p.m. - 11:25 p.m.
YWG
-
MCO
10h 15m1 stop
Porter Airlines Logo
8:30 a.m. - 3:30 p.m.
MCO
-
YWG
8h 00m1 stop
C$ 313Porter Airlines
Wed, 25 Feb - Wed, 4 Mar
Porter Airlines Logo
12:10 p.m. - 11:25 p.m.
YWG
-
MCO
10h 15m1 stop
Porter Airlines Logo
8:30 a.m. - 3:30 p.m.
MCO
-
YWG
8h 00m1 stop
C$ 315Porter Airlines
Wed, 25 Feb - Wed, 4 Mar
Porter Airlines Logo
12:10 p.m. - 11:25 p.m.
YWG
-
MCO
10h 15m1 stop
Porter Airlines Logo
8:30 a.m. - 3:30 p.m.
MCO
-
YWG
8h 00m1 stop
C$ 318Porter Airlines
Mon, 23 Feb - Wed, 25 Feb
Multiple Airlines Logo
12:20 p.m. - 8:16 p.m.
YWG
-
MCO
6h 56m1 stop
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
MCO
-
YWG
10h 09m2 stops
C$ 324Multiple Airlines
Mon, 23 Feb - Wed, 25 Feb
Multiple Airlines Logo
12:20 p.m. - 8:16 p.m.
YWG
-
MCO
6h 56m1 stop
Multiple Airlines Logo
6:00 a.m. - 3:09 p.m.
MCO
-
YWG
10h 09m2 stops
C$ 325Multiple Airlines
Mon, 19 Jan - Sat, 31 Jan
Multiple Airlines Logo
8:00 a.m. - 7:43 a.m.
YWG
-
MCO
22h 43m1 stop
Multiple Airlines Logo
9:46 p.m. - 3:09 p.m.
MCO
-
YWG
18h 23m1 stop
C$ 327Multiple Airlines
Tue, 31 Mar - Wed, 13 May
United Airlines Logo
2:15 p.m. - 9:55 p.m.
YWG
-
MCO
6h 40m1 stop
United Airlines Logo
10:30 a.m. - 8:48 p.m.
MCO
-
YWG
11h 18m1 stop
C$ 328United Airlines
Tue, 24 Feb - Tue, 3 Mar
WestJet Logo
12:20 p.m. - 8:16 p.m.
YWG
-
MCO
6h 56m1 stop
WestJet Logo
9:15 p.m. - 7:09 p.m.
MCO
-
YWG
22h 54m1 stop
C$ 329WestJet
Fri, 20 Feb - Tue, 24 Feb
Porter Airlines Logo
12:10 p.m. - 11:25 p.m.
YWG
-
MCO
10h 15m1 stop
Porter Airlines Logo
8:30 a.m. - 3:30 p.m.
MCO
-
YWG
8h 00m1 stop
C$ 331Porter Airlines
Useful Info

Good to know

Low seasonOctober
Cheapest flightC$ 165
Best time to beat the crowds (26% less expensive on average)
Most popular time to fly (17% more expensive on average)
Flight from Winnipeg to Orlando

When to book flights from Winnipeg to Kissimmee

Are your dates flexible? Find out the best times to travel from Winnipeg to Kissimmee based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Winnipeg to Kissimmee

  • Which airports will I be using when flying from Winnipeg to Kissimmee?

    When flying out of Winnipeg you’ll be using Winnipeg. Kissimmee does not have its own airport so you’ll be flying into nearby Orlando airport, which is 17.6 km away.

  • How long does a flight from Winnipeg to Kissimmee take?

    Direct flights cover the 4,409 km separating Winnipeg and Kissimmee in about 4h 03m.

  • How many flights are there between Winnipeg and Kissimmee?

    1 direct flights run between Winnipeg and Kissimmee on a daily basis. On average, there are about 7 departures each week.

  • What’s the cheapest day of the week to fly between Winnipeg and Kissimmee?

    Consider leaving on a Thursday and avoid Saturdays if you are looking for the best rates. For your return to Winnipeg, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

  • How does KAYAK find such low prices on flights from Winnipeg to Kissimmee?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Kissimmee.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Kissimmee?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kissimmee from Winnipeg is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Kissimmee?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Kissimmee with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Kissimmee?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Kissimmee from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Winnipeg to Kissimmee?

    In the last 72 hours, the cheapest one-way ticket between Winnipeg and Kissimmee found on KAYAK was with Porter Airlines for C$ 148. United Airlines offered a round-trip connection from C$ 202 and Delta from C$ 262.

Top tips for finding cheap flights from Winnipeg to Kissimmee

  • There is no airport in Kissimmee. Instead, you’ll be flying into Orlando Airport when flying between Winnipeg and Kissimmee.
  • The cheapest flight from Winnipeg to Kissimmee was found 33 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is October.

Top 5 airlines flying from Winnipeg to Kissimmee

 
Need help choosing which airline to fly with from Winnipeg to Kissimmee? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 394 reviews
7.6Food
8.2Boarding
8.6Crew
8.0Comfort
7.0Entertainment
Airline reviews

Organization and the adjusted times but the snacks could be of a bigger portion

8.0 ExcellentAnonymous, Nov 2025
YYZ - PHX
Read more Porter Airlines reviews

Organization and the adjusted times but the snacks could be of a bigger portion

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

It was beautiful easy and smooth experience. Thank you. Will definitely get Delta for my next travel.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Quick and seamless boarding. No entertainment but fast Starlink wifi for this short trip and the staff was really friendly.

I dread trans-Pacific flights. They are very long. This was my first time on Universal, and it was my best crossing ever. The staff were professional, the hospitality was great, and the food was delicious. The entertainment system filled the long flight hours. I will seek out Universal flights from now onwards. 🙂

Always wish for more healthy, gluten free options. We have to bring our own.

The food quality sucks. One must starve if they do not eat flesh Or wheat based products Some variety would be expected. The trivial amount of snacks and or food is inhumane

We Left Calgary 1/2 hour late and that made for a tight connection in Denver. After arriving everything was done to help us make our connection. That was a great effort. Thank You United

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

My flight was cancelled due to weather but Westjet got me on a new flight in a timely and efficient manor.

I was seated near a "stinky" person. That's not the fault of Westjet🙁😶‍🌫️

Do not fly on WestJet if you have a connection. It failed to integrate with my connecting Delta flight and I almost missed it.

No internet, not even westjet connect makes for a boring flight

Our first flight from LAX to Winnipeg was changed but you never informed us at all. It went from a nonstop flight to a stay at Calgary. This impacted our trip negatively as we arrived much later than we planned to. Our returning flight was horrible. The flight was delayed 6 hours!! And we were NOT going to wait that long. The only way we got on our original flight was running there. However all of our suitcases were now coming on the delayed flight. It was the worst experience we ever had flying. I want my money back.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

The staff could not have been any friendlier. Lots of usb ports on our aircraft.

The airplane is way too tight, you can hardly enter into your row to sit.. more like kids seats than adults.

First message when all on board was that we didnt have a pilot, then they found one, then it was something about the bridge something not working, they will either fix or do manually. Flight of course was leaving late with all the cruise guests worrying about making it to their ship in time. Then only some luggage made it off the ship. Around 15 to 20 people waiting. 45 min later arrived except mine. I asked the rep at the luggage conveyor, he asked me my name. Then said it was not picked up with the first batch so they put it in a room. I was going to take public transport but now worried about time so took a taxi that cost me $65 USD

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Horrible, experience, 5 hours delay, they changed gates 3 times, the last one we had to wait for 1::30 hre for the door to open to get to that gate. 0 apologies from Air Canada, they don’t care at all about their passengers

Late departing. Late arriving. More worried about limiting bags on board. Free beer and wine a nice surprise.

Upgraded to sit at the exit door so good leg room.

Everything you need to know for your flight from Winnipeg to Kissimmee

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