C$ 249 Find Cheap Flights from Calgary 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 Calgary to Kissimmee departing on 2/9. 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$ 416
Typical prices: C$ 579-C$ 860
Multiple Airlines
Fri 21/8Tue 25/8
YYC - MCO • 1 stop
Cheapest direct flights
C$ 519
Typical prices: C$ 578-C$ 881
WestJet
Sun 30/8Sat 5/9
YYC - 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
Useful Info
Flight Deals

Cheap Flights from Calgary to Kissimmee (YYC-MCO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Calgary 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 Calgary to Kissimmee

Fri, 21 Aug - Tue, 25 Aug
Multiple Airlines Logo
7:00 a.m. - 8:00 p.m.
YYC
-
MCO
11h 00m
1 stop
Multiple Airlines Logo
1:45 p.m. - 9:50 p.m.
MCO
-
YYC
10h 05m
1 stop
C$ 416Multiple Airlines
Wed, 19 Aug - Wed, 26 Aug
Multiple Airlines Logo
7:00 a.m. - 6:33 p.m.
YYC
-
MCO
9h 33m
1 stop
Multiple Airlines Logo
7:57 a.m. - 9:50 p.m.
MCO
-
YYC
15h 53m
1 stop
C$ 420Multiple Airlines
Thu, 27 Aug - Mon, 31 Aug
Multiple Airlines Logo
7:00 a.m. - 10:14 p.m.
YYC
-
MCO
13h 14m
1 stop
Multiple Airlines Logo
7:45 a.m. - 9:50 p.m.
MCO
-
YYC
16h 05m
1 stop
C$ 423Multiple Airlines
Fri, 28 Aug - Mon, 31 Aug
Multiple Airlines Logo
11:40 a.m. - 10:14 p.m.
YYC
-
MCO
8h 34m
1 stop
Multiple Airlines Logo
10:03 a.m. - 5:10 p.m.
MCO
-
YYC
9h 07m
1 stop
C$ 427Multiple Airlines
Fri, 28 Aug - Mon, 31 Aug
Multiple Airlines Logo
11:40 a.m. - 10:14 p.m.
YYC
-
MCO
8h 34m
1 stop
Multiple Airlines Logo
10:03 a.m. - 5:10 p.m.
MCO
-
YYC
9h 07m
1 stop
C$ 429Multiple Airlines
Wed, 12 Aug - Wed, 19 Aug
Multiple Airlines Logo
7:00 a.m. - 6:33 p.m.
YYC
-
MCO
9h 33m
1 stop
Multiple Airlines Logo
7:57 a.m. - 9:50 p.m.
MCO
-
YYC
15h 53m
1 stop
C$ 439Multiple Airlines
Thu, 10 Sep - Fri, 18 Sep
Multiple Airlines Logo
12:20 a.m. - 10:10 p.m.
YYC
-
MCO
19h 50m
1 stop
Multiple Airlines Logo
12:52 p.m. - 9:50 p.m.
MCO
-
YYC
10h 58m
1 stop
C$ 444Multiple Airlines
Wed, 12 Aug - Tue, 18 Aug
Multiple Airlines Logo
7:00 a.m. - 6:33 p.m.
YYC
-
MCO
9h 33m
1 stop
Multiple Airlines Logo
1:45 p.m. - 9:50 p.m.
MCO
-
YYC
10h 05m
1 stop
C$ 449Multiple Airlines
Fri, 21 Aug - Wed, 26 Aug
Multiple Airlines Logo
7:00 a.m. - 10:14 p.m.
YYC
-
MCO
13h 14m
1 stop
Multiple Airlines Logo
1:45 p.m. - 9:50 p.m.
MCO
-
YYC
10h 05m
1 stop
C$ 450Multiple Airlines
Wed, 5 Aug - Tue, 11 Aug
Multiple Airlines Logo
7:00 a.m. - 6:33 p.m.
YYC
-
MCO
9h 33m
1 stop
Multiple Airlines Logo
7:45 a.m. - 5:10 p.m.
MCO
-
YYC
11h 25m
1 stop
C$ 451Multiple Airlines
Useful Info

Good to know

Low seasonJune
Cheapest flightC$ 249
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (4% more expensive on average)
Flight from Calgary to Orlando Airport

When to book flights from Calgary to Kissimmee

Are your dates flexible? Find out the best times to travel from Calgary 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 Calgary to Kissimmee

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

    When flying out of Calgary you’ll be using Calgary. 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 Calgary to Kissimmee take?

    Direct flights cover the 5,969 km separating Calgary and Kissimmee in about 5h 15m.

  • How many flights are there between Calgary and Kissimmee?

    3 direct flights run between Calgary and Kissimmee on a daily basis. On average, there are about 24 departures each week.

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

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

  • How does KAYAK find such low prices on flights from Calgary 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 Calgary to Kissimmee.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kissimmee from Calgary 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 Calgary 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 Calgary with another airline.

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

    In the last 5 days, the cheapest one-way ticket between Calgary and Kissimmee found on KAYAK was with WestJet for C$ 184. Air Canada offered a round-trip connection for C$ 248 and United Airlines for C$ 342.

Top tips for finding cheap flights from Calgary to Kissimmee

  • There is no airport in Kissimmee. Instead, you’ll be flying into Orlando Airport when flying between Calgary and Kissimmee.
  • The cheapest flight from Calgary to Kissimmee was found 64 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 January.

Top 5 airlines flying from Calgary to Kissimmee

 
Need help choosing which airline to fly with from Calgary 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 443 reviews
8.2Boarding
8.6Crew
6.9Entertainment
7.5Food
8.0Comfort
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.

We were very offended Reserva check in agent in Calgary. Erroneously profiled and reprimanded for using Reserve line . Hadn't even looked at tickets. We were in fact Reserve passengers

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

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

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. :)

Reserve check-in was very slow compared to regular check-in. Internet was slow

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

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

Porter uses the intelligent and logical way of boarding a plane - from the back.

They really communicated well advised well in advance of a delay. Contacted to tell me it was almost time to go and to do a check in.

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

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

Plane 3 hours late. Missed connection. No help from gate staff. App horrible. Lost connection repeatedly. No service desk. Finally got help from young girl driving cart.

Horrible; seating was atrocious - inadequate leg room and seat width tight even for a small individual. Profits shouldn’t be everything!

I flew basic economy, so it was what I expected. Crew was nice though, and flight was quick. Would recommend for flights under 6 hours, otherwise would upgrade to something with more leg room.

Airline staff was good the checkin process was ok but the plane itself was very bad the comfort was worst it was worst and the most stiff 5 hours of my life i felt claustrophobic

Calgary desperately needs a star alliance lounge in the transborder area for United.

Leg room was lacking. Legs crammed into seat in front.

Flight was delayed but reasonable notice and communication was always there for the passengers.

I think it would have been better to get a heads up to download the app before getting on the plane as I only had wifi in the airport and didn’t realize the plane was an older one. Maybe a little more communication before hand would be lovely. The seats as always were crammed and uncomfortable and trying to convince people to spend an extra 150 so that we have an extra foot of leg room was less then ideal.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

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

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

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Seats were comfortable and leg room was good. Slight delay for boarding but nothing too bad. Would fly with them again.

The departure and arrival was on time. The fact that I could load my boarding tickets on the American airlines app.

Horrible experience, delays after delays. A flight that should arrive 11:50pm just landed past 1 am, and another 30min waiting for the baggage to come out. Very disappointing.

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

Due to the long delays and rescheduling boarding was horrible. However, the gate staff and the flight attendants went above and beyond to remedy our frustrations. They were able to handle every potential harsh situation with Grace, compassion and coolness of head. Kudos to the MIA Gate A12 and night crew of flight 1572 YYZ to MIA.

I liked nothing about this particular flight. Not only it was initially delayed for two hours due to late arrival of the plane, but the flight attendants were also very late to show up coming from a hotel (based on the announcement made by the gate agent). They did not arrive on another late flight, so why couldn't they be on time? Total disrespect of the passengers!! The plane itself was cramped and the seats super uncomfortable. To top off the poor experience, my video screen did not work. To summarize: flight delayed for 3 hours, cramped and no entertainment (for me).

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

Pros: The airplane was new and had in-flight entertainment (tablet behind seats) with new movies instead of watching on personal devices. Cons: the flight time was changed without informing us. When I booked the flight, the time was 13:30pm (also in the email confirmation). However, when I reached the airport, the time was conveniently changed to 14:55pm. When I asked at the counter, they said the flight always took off at this time. The booking was made by Air Canada, but the flight was operated by United.

United did not permit online check-in from home as document scans were not getting uploaded. This should be fixed their app

Flights delayed over 4 hours with no compensation. No agents at counters to assist with re-booking.

It took 5 hour to get a crew to D Ice the plan. We had to sit on the runway for 5 hrs. in Calgary. It snows most of the winter. No proactive plan. In addition, after 3 calls to customer service they couldn't figure out how to have my wife and myself sit together on her birthday weekend. Everybody kept passing the buck. No decision from customer service, luggage drop off or check in team. The experience was a complete mess! I don't think we'll ever fly on this airline again.

The wifi I paid for did not work. The seats are tight.

There were no free snacks…little pretzel bag or cookies like we had on our flight out.

We culd not check in ovr the inrnt since e did not have the unied airlns boing efence Tis is alays a issue when boing coe shae flits witstr allince

They could have served at least some cookies with coffee or tea or juice.

The flight was on time, boarding was smooth. The crew was did an excellent job traffic controlling as people boarded.

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

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