C$ 279 Find Cheap Flights from Winnipeg to Kissimmee – Compare and Save

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 21/7. 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$ 385
Typical prices: C$ 377-C$ 708
WestJet
Fri 20/11Fri 27/11
YWG - MCO • 1 stop
Cheapest direct flights
C$ 763
Typical prices: C$ 539-C$ 689
WestJet
Fri 20/11Fri 27/11
YWG - MCO • Direct
Arrival airport
You can’t fly directly to Kissimmee. It is served by Orlando (MCO), located 17.6 km from Kissimmee.
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Flight Deals
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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

Fri, 20 Nov - Fri, 27 Nov
WestJet Logo
12:20 p.m. - 8:24 p.m.
YWG
-
MCO
7h 04m
1 stop
WestJet Logo
11:10 a.m. - 7:15 p.m.
MCO
-
YWG
9h 05m
1 stop
C$ 385WestJet
Sun, 11 Oct - Fri, 16 Oct
WestJet Logo
10:45 a.m. - 7:45 p.m.
YWG
-
MCO
8h 00m
1 stop
WestJet Logo
5:05 p.m. - 12:55 a.m.
MCO
-
YWG
8h 50m
1 stop
C$ 408WestJet
Tue, 24 Nov - Tue, 1 Dec
WestJet Logo
12:20 p.m. - 8:24 p.m.
YWG
-
MCO
7h 04m
1 stop
WestJet Logo
9:15 p.m. - 7:15 p.m.
MCO
-
YWG
23h 00m
1 stop
C$ 418WestJet
Fri, 18 Sep - Mon, 21 Sep
WestJet Logo
7:55 p.m. - 7:45 p.m.
YWG
-
MCO
22h 50m
1 stop
WestJet Logo
5:05 p.m. - 12:55 a.m.
MCO
-
YWG
8h 50m
1 stop
C$ 426WestJet
Sun, 18 Oct - Fri, 30 Oct
WestJet Logo
6:00 a.m. - 7:45 p.m.
YWG
-
MCO
12h 45m
2 stops
WestJet Logo
11:10 a.m. - 7:15 p.m.
MCO
-
YWG
9h 05m
1 stop
C$ 428WestJet
Thu, 19 Nov - Mon, 30 Nov
WestJet Logo
8:05 p.m. - 8:24 p.m.
YWG
-
MCO
23h 19m
1 stop
WestJet Logo
11:10 a.m. - 7:15 p.m.
MCO
-
YWG
9h 05m
1 stop
C$ 432WestJet
Sun, 18 Oct - Fri, 30 Oct
WestJet Logo
7:10 p.m. - 10:40 a.m.
YWG
-
MCO
14h 30m
2 stops
WestJet Logo
11:10 a.m. - 12:55 a.m.
MCO
-
YWG
14h 45m
2 stops
C$ 434WestJet
Wed, 14 Oct - Sun, 18 Oct
WestJet Logo
6:15 a.m. - 10:40 a.m.
YWG
-
MCO
27h 25m
1 stop
WestJet Logo
8:35 p.m. - 12:55 a.m.
MCO
-
YWG
29h 20m
1 stop
C$ 452WestJet
Tue, 10 Nov - Tue, 17 Nov
WestJet Logo
5:00 a.m. - 8:24 p.m.
YWG
-
MCO
14h 24m
1 stop
WestJet Logo
9:15 p.m. - 11:35 a.m.
MCO
-
YWG
15h 20m
1 stop
C$ 459WestJet
Tue, 10 Nov - Tue, 17 Nov
WestJet Logo
5:00 a.m. - 8:24 p.m.
YWG
-
MCO
14h 24m
1 stop
WestJet Logo
9:15 p.m. - 11:35 a.m.
MCO
-
YWG
15h 20m
1 stop
C$ 461WestJet
Useful Info

Good to know

Low seasonSeptember
Cheapest flightC$ 279
Best time to beat the crowds (32% less expensive on average)
Most popular time to fly and prices are also 11% lower on average.
Flight from Winnipeg to Orlando Airport

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.

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

    Consider leaving on a Friday and avoid Sundays 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 Tuesdays.

  • 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 5 days, the cheapest one-way ticket between Winnipeg and Kissimmee found on KAYAK was with WestJet for C$ 160. United Airlines offered a round-trip connection from C$ 245 and WestJet from C$ 252.

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 81 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 January, February and March. The cheapest month to fly is September.

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.
7.9
Porter AirlinesOverall score based on 442 reviews
8.2Boarding
7.5Food
7.9Comfort
6.9Entertainment
8.6Crew
Airline reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

4.0 OkayJeff, Jul 2026
YYZ - SFO
Read more Porter Airlines reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

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

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.

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

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Everything could and should be better. We are paying for, it's not a favor, it's a service and should involve quality, responsibility and respect.

Round trip flight to Canada and back to the US was smooth and efficient.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

I have to say that Delta has improved their service radically since I flew with them last. I purposely have avoided flying with them for years owing to absolutely terrible service. This is no longer the case, I am glad to say.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

I couldn’t make my first flight due to weather delays trapping us in the town we were in. Then I had to buy a new ticket

Much better than Spirit. I was please by the easy fast check in and boarding

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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

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.

Lots of overhead storage and a good crew and service.

On time. Friendly and efficient staff at check in and flight crew.

Very good over all , would have been nice to have entertainment on the flight

It was an awesome experience flying with Westjet. This was my first domestic flight experience in Canada.

The flight itself was fine, but two of the ladies at the gate were extremely rude to a few of us in line. Their customer service really needs some help. I’ve always had good experiences with WestJet until these two ladies. They had the worst attitudes and really left a bad taste in my mouth after a good trip

Smooth process, on time. Everything ran perfectly. It would be nice to have in flight entertainment and better food choices but these were short flights so not a big deal

Flight got cancelled. I had to spend many hours on phone to have it rescheduled at my convenience

I like the fact air Canada is on time The food you guys serve is not good

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

Very tight leg room and not a fan of the new policy on no free carry on luggage. Besides that, it was fine.

Flight delay, cancellation rescheduling and misdirected luggage which created some stress. It all worked out in the end.

The flight was delayed several times, however , they kept me well informed with enough advance warning that I had not left home yet

Sat on the tarmac with no ventilation for almost an hour, without a single word from the crew. Appalling. When Air Canada goes bankrupt, again, almost everyone in Canada will be cheering.

If you have checked the status of my booking you would have seen that it was cancelled. And the travelers insurance we purchased only covered $100 per ticket. So my overall experience with kayak and air canada is poor

The plane for my second flight was reassigned. We had to wait for them to get a different plane out of the hangar and call in a crew

Send me 20 dollars and i will do the survey. You survey people think we do things in life to do surveys.

It was swiss air flight and they were very helpful and kind

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

Complete your trip to Kissimmee with a hotel stay or car rental