C$ 228 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 21/7. 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$ 347
Typical prices: C$ 424-C$ 281
WestJet
Fri 2/10Mon 5/10
YWG - MCO • 1 stop
Cheapest one-way flights
C$ 235
Typical prices: C$ 217-C$ 283
Air Canada
Tue 21/7
YWG - MCO • 1 stop
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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We hope you love your trip to Kissimmee!
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

Fri, 2 Oct - Mon, 5 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$ 347WestJet
Sat, 25 Jul - Fri, 31 Jul
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$ 383WestJet
Wed, 12 Aug - Wed, 19 Aug
WestJet Logo
6:05 p.m. - 10:40 a.m.
YWG
-
MCO
15h 35m
1 stop
WestJet Logo
5:05 p.m. - 12:55 a.m.
MCO
-
YWG
8h 50m
1 stop
C$ 389WestJet
Wed, 29 Jul - Fri, 7 Aug
WestJet Logo
5:15 p.m. - 10:40 a.m.
YWG
-
MCO
16h 25m
1 stop
WestJet Logo
5:05 p.m. - 12:55 a.m.
MCO
-
YWG
8h 50m
1 stop
C$ 391WestJet
Tue, 7 Jul - Tue, 14 Jul
WestJet Logo
6:05 p.m. - 10:40 a.m.
YWG
-
MCO
15h 35m
1 stop
WestJet Logo
5:05 p.m. - 12:55 a.m.
MCO
-
YWG
8h 50m
1 stop
C$ 398WestJet
Fri, 10 Jul - Tue, 14 Jul
United Airlines Logo
8:45 a.m. - 8:29 p.m.
YWG
-
MCO
10h 44m
2 stops
United Airlines Logo
4:21 p.m. - 10:33 p.m.
MCO
-
YWG
7h 12m
1 stop
C$ 402United Airlines
Wed, 22 Jul - Tue, 28 Jul
United Airlines Logo
7:00 a.m. - 9:55 p.m.
YWG
-
MCO
13h 55m
1 stop
United Airlines Logo
5:19 p.m. - 11:52 a.m.
MCO
-
YWG
19h 33m
2 stops
C$ 404United Airlines
Sat, 15 Aug - Sat, 22 Aug
Delta Logo
3:58 p.m. - 11:58 p.m.
YWG
-
MCO
7h 00m
1 stop
Delta Logo
7:04 a.m. - 3:08 p.m.
MCO
-
YWG
9h 04m
1 stop
C$ 405Delta
Mon, 6 Jul - Tue, 14 Jul
WestJet Logo
6:05 p.m. - 10:40 a.m.
YWG
-
MCO
15h 35m
1 stop
WestJet Logo
5:05 p.m. - 12:55 a.m.
MCO
-
YWG
8h 50m
1 stop
C$ 409WestJet
Sat, 19 Sep - Sat, 26 Sep
WestJet Logo
4:25 p.m. - 10:40 a.m.
YWG
-
MCO
17h 15m
1 stop
WestJet Logo
8:35 p.m. - 8:20 p.m.
MCO
-
YWG
24h 45m
1 stop
C$ 416WestJet
Useful Info

Good to know

Low seasonOctober
Cheapest flightC$ 235
Best time to beat the crowds (30% less expensive on average)
Most popular time to fly and prices are also 9% 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 Tuesdays 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 72 hours, the cheapest one-way ticket between Winnipeg and Kissimmee found on KAYAK was with Porter Airlines for C$ 144. United Airlines offered a round-trip connection from C$ 181 and WestJet from C$ 241.

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 59 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 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 436 reviews
7.6Food
8.2Boarding
8.0Comfort
7.0Entertainment
8.6Crew
Airline reviews

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

10.0 ExcellentAnonymous, Apr 2026
YHM - YHZ
Read more Porter Airlines reviews

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

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

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

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.

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!

N Everything was perfect from boarding to assistance to baggage in Tampa

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Seats very comfortable; service efficient and pleasant; flight was on-time; boarding organized.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Good but airlines getting smaller. I didn't like the meal but the service was fine. Flight was fine and luggage arrived. So good.

They were fast and I like how they used to entertainment system to play video about the safety.

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.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Given I (and I’m assuming most people) have both carry in and a personal item included in their fare, I find it very unfair that on neither of my flights I was able to use the overhead for my small backpack because they were completely rammed with luggage, people personal items, jackets, hats and other items. So the only item I brought in had to be stuffed under my seat while they had their leg room and sat comfortable with all of their items in the overhead. This has to stop because I was uncomfortable on both flights when I only had one smaller item that could not be checked due to its contents (medication etc). Plenty of people could have checked theirs but chose not to and then took up the space allotment for 2 people.

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

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.

Flight and attendance were very good we had 2 hour delay that took the shine of it

Be careful about the bad policy and when purchasing seats

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

My seat was not comfortable. Flight was smooth. Regretfully we had two delays before takeoff

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

My seat was covered in vomit and I will be reaching out to Air Canada

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 😒

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

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