Hello!
We are also from Calgary and just got home from our first DCL cruise at the beginning of May.
We looked at the Disney flight package but found the times were so inconvenient.
Ended up booking through Expedia which is where we found the best rates at the time (although still expensive). Our flights for four totalled around $2000 (Cdn).
We booked our flights all through United. Left Calgary at 7am, the day before sailing, connected in Denver and flew through to Orlando. We had an hour wait in Denver and ended up in Orlando at 4pm. The hour connection was perfect in Denver as it gave us a chance to feed our 3 and 5 year old and stretch our legs. Of course, with a layover of only an hour there was potential to miss the next flight or not have our luggage transferred. I was quite nervous about this flight but luckily no lost luggage and everything timed out perfectly.
In Orlando we decided to stay at the Sheraton by the airport. Their free shuttle picked us up at the airport. The shuttle also took us to a nearby restaurant for supper later that night. The next morning the shuttle took us back to the airport at our requested time and dropped us off right at the Disney buses. From there we took the Disney bus to the port (we had purchased the Disney transfers - recommend it, very easy and convenient).
On the way home we again took the Disney transfer to the airport. First flight was at 1:30pm (we were at the airport by 10am so a bit of a wait). Flew to Chicago and from Chicago to Calgary (2 hour layover). Landed in Calgary approx 8:30pm. All in all, everything worked out perfectly.
Expect to have the time of your life on this cruise - if you have any other questions, please feel free to ask!!