Hmm, it's a Friday. I'd have no issues with my work, but my wife only gets 1 requested day off per year (School schedule, she gets all the usual breaks, but they only get 1 actual work day throughout the year to ask off). So we'd have to try and get a flight sometime after 4pm on Thursday. Might be tricky, don't think there are too many of those going to Orlando from Winnipeg! Definitely want to try to be there on the 1st though!
Lol, through a quick peak at this October, the best flight I can see leaves Winnipeg at 4:30pm Thursday and arrives at 5:23am on Friday, with a nice 6 hour layover in Denver of all places!