My reasons for driving vs flying were usually to do with how long I'd be there. If I was going for one day then flying was preferable since falling asleep on the way home isn't a big deal. If I was going for multiple days then driving was preferable so that I'd have a car and be able to go places after finishing at the office. Flying was preferable in winter in case the roads were in bad shape. Driving was preferable on Fridays so that I could visit friends afterwards and come back the next day. Flying was preferable during the Calgary Stampede to avoid having to deal with the excess traffic in Calgary (plus WestJet did a cowboy-themed safety lecture during Stampede which was kind of neat).