So I've done some discussing with my mother. She flew to Calgary last summer and gave me some helpful advice.
There are three good cheap companies to fly with domestically in Canada: Swoop, Westjet, and flair. One of these companies goes to Edmonton, not Calgary though I forget which one. More often than not it is cheaper to fly out of Kitchener than it is to fly out of Toronto. Kitchener is a much smaller and therefore less busy airport even during the long weekend. Kitchener would be a longer drive for you guys though (about 2 hours from Orillia to Kitchener vs 1 and a half hours from Orillia to Toronto).
Because I will be working a co op job through my university I am not guaranteed any time off during the work term. It is the university policy to not allow students to take time off however my two older brothers who are in the same program were able to take the occasional Friday off if they made up lost time during the next week. So I will not be sure if I can get the Friday off until the work term starts the week of May 9 at the latest.
Because of the uncertainty of the Friday I decided to look at flights early Saturday morning. Yes, I would miss the first day of the convention, but I would still be able to get a full Saturday and Sunday. Flair has a flight that leaves 6:00am Saturday morning from Kitchener on a 4h15m direct flight to Calgary. This would put me there at 8:15am Calgary time. Monday is a holiday and they have a return flight leaving at 9:00am Calgary on a 3h45m direct flight to Kitchener. This would allow 2 full days of the convention and would require me to stay 2 full nights. The round trip for these two flights costs $197 before tax and baggage fees. Link: HERE
I could easily get myself to Kitchener Friday night after work and catch the flight Saturday morning. While unlikely, I could try to catch a few more Z's on the plane and arrive in Calgary around 8:15am. I will have the 22 of may off as it is a holiday so I could use that time to fly to Kitchener for around 3:00pm, and be home in Windsor by supper time.
You guys are probably planning to go for all 3 days, but I would be all too happy to join up on day 2 and 3. NewBrody Schankerz
I assume you guys will be going up together. If you guys are planning on splitting a hotel room and have space for one more I would be glad to chip in for the nights I'm there.
I haven't done any research on how far the convention centre is from the airport or what the best method of getting from the airport into town is, but this is a good start I think. Thoughts?