C$ 249 Find Cheap Flights from Calgary 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 Calgary to Kissimmee departing on 3/10. 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$ 492
Typical prices: C$ 758-C$ 402
American Airlines
Wed 23/9Mon 28/9
YYC - MCO • 1 stop
Cheapest direct flights
C$ 585
Typical prices: C$ 908-C$ 483
WestJet
Mon 26/10Wed 4/11
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

Wed, 23 Sep - Mon, 28 Sep
American Airlines Logo
6:45 a.m. - 9:16 p.m.
YYC
-
MCO
12h 31m
1 stop
American Airlines Logo
3:39 p.m. - 11:20 p.m.
MCO
-
YYC
9h 41m
2 stops
C$ 492American Airlines
Wed, 10 Jun - Mon, 15 Jun
American Airlines Logo
1:00 p.m. - 12:13 a.m.
YYC
-
MCO
9h 13m
1 stop
American Airlines Logo
6:34 a.m. - 9:43 p.m.
MCO
-
YYC
17h 09m
1 stop
C$ 502American Airlines
Mon, 8 Jun - Mon, 15 Jun
American Airlines Logo
6:45 a.m. - 8:12 p.m.
YYC
-
MCO
11h 27m
1 stop
American Airlines Logo
6:34 a.m. - 9:43 p.m.
MCO
-
YYC
17h 09m
1 stop
C$ 503American Airlines
Wed, 14 Oct - Sat, 24 Oct
Air Canada Logo
11:55 p.m. - 10:54 a.m.
YYC
-
MCO
8h 59m
1 stop
Air Canada Logo
8:00 a.m. - 3:57 p.m.
MCO
-
YYC
9h 57m
1 stop
C$ 505Air Canada
Mon, 19 Oct - Thu, 22 Oct
WestJet Logo
6:30 p.m. - 10:40 a.m.
YYC
-
MCO
14h 10m
2 stops
WestJet Logo
11:30 a.m. - 10:00 p.m.
MCO
-
YYC
12h 30m
2 stops
C$ 506WestJet
Tue, 20 Oct - Sat, 24 Oct
Delta Logo
7:45 a.m. - 10:55 p.m.
YYC
-
MCO
13h 10m
2 stops
Delta Logo
6:40 a.m. - 12:47 p.m.
MCO
-
YYC
8h 07m
1 stop
C$ 516Delta
Thu, 11 Jun - Tue, 16 Jun
American Airlines Logo
6:45 a.m. - 11:25 p.m.
YYC
-
MCO
14h 40m
1 stop
American Airlines Logo
6:30 a.m. - 11:42 p.m.
MCO
-
YYC
19h 12m
1 stop
C$ 517American Airlines
Mon, 19 Oct - Wed, 21 Oct
United Airlines Logo
6:45 a.m. - 11:47 p.m.
YYC
-
MCO
15h 02m
1 stop
United Airlines Logo
8:50 a.m. - 5:30 p.m.
MCO
-
YYC
10h 40m
1 stop
C$ 518United Airlines
Mon, 19 Oct - Thu, 22 Oct
WestJet Logo
6:30 p.m. - 10:40 a.m.
YYC
-
MCO
14h 10m
2 stops
WestJet Logo
11:30 a.m. - 6:10 p.m.
MCO
-
YYC
8h 40m
1 stop
C$ 528WestJet
Mon, 19 Oct - Wed, 21 Oct
United Airlines Logo
12:30 p.m. - 11:53 p.m.
YYC
-
MCO
9h 23m
1 stop
United Airlines Logo
9:10 a.m. - 9:48 p.m.
MCO
-
YYC
14h 38m
2 stops
C$ 530United Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flightC$ 245
Best time to beat the crowds (22% less expensive on average)
Most popular time to fly and prices are also 7% lower 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$ 176. Air Canada offered a round-trip connection from C$ 334 and United Airlines from C$ 334.

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 September.

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

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

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.

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.

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

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

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.

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.

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

From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.

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

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

Better movie options. More diligence on the size and amount of bags people bring on board. Lady across aisle from me had a bucket style bag that would only go so far under the seat in front of her. She was not told once that the whole bag is supposed to be under the seat. Crew is very hardworking however.

I didn’t have any food but my Prosecco hit the spot. We left on time and the crew was friendly.

Flight didn’t happen because both my connections were lost and Toronto wouldn’t let me board. I was checked in to all 3 flights at the check-in fest in Dublin.

I wasn’t able to book or pay for a seat and they forgot to check me in for my third flight so I spent 24 hours in Toronto waiting for another one.

Flight was delayed for 5hours. Food vouchers just aren’t good enough

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

No kiosk to help pre boarding unlike other airlines, still lost the luggage despite its own crew/TSA or security tagging it, poor handling of lost luggage and possibly compensation is likely poor too.

Everything was great until we had to get our bags. The bags came out in several different batches over 90 minutes after we landed maybe more we got our bags. So much for the old West Jet where they promised bags in 20 minutes. I Next time I will pack lighter and go with a carry-on.

The flight was full and good as could be expected. We arrived early which is always a good thing.

I was tired enough to fall asleep soon after takeoff and slept until "we are starting our descent to Toronto" announcement. That's not bad at all.

It was great to have a vegetarian meal option, but departure was delayed because they had oversold the flight. Air Canada, you’re in charge of how many tickets are sold: don’t oversell!

The lead flight attendent was outstanding. We were delayed waiting for a connection and she kept us up-to-date with a great sense of humor. She also made sure a passenger in the back of the plane was sble to get out first to make a connection. She needs to be recognized by your company! She is awesome!

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

Very bed experience never want to travel air canada anymore

Was not sent a link to check in online. Tried to check in online using website. Site didn’t work. Called support line, was told it often didn’t work. Went to counter at airport to check bags and get boarding passes. Had to stand in a lineup. They were unable to tell me how much to pay. Had to take a paper to another counter, took a long time to be told what I owed. I fondly remember the days of checking in online, getting my boarding pass digitally, paying for my luggage on line, scanning my passport at the airport to get my luggage tags, and putting my luggage on the conveyor. Easy peasy. Air Canada has really taken a step back in time, and made what was an easy check in experience to one that seemed unduly long and frustrating.

Really out of Air Canada's control due to long delay because of mechanical issues. While doing their best, disappointed by their assumption that all passengers have smart phones. Should have communicated food voucher availability at gate area. Late arrival cost me an extra $51 because public transit was not available, Otherwise, feel Air Canada did their best dealing with their challenges. Will likely continue using them in the future.

They canceled my flight, I had to rent a car, drive 14 hours. They tell to go on line for a refund, but only offer $24 for a $210 flight and you can’t get hold of anybody by phone and no help from staff at the airport.

I wish to travel with Air Canada for my next trip

They were very attentive, polite, professional and great customer service skills.

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

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