The only way you could use Resort Check in (based on the routing indicated in the thread) is if your bags were only checked through to Chicago (and you physically picked up your bags in Chicago, and re-checked them for your flight to Canada. In effect, this would make your flight from Orlando a domestic flight, and eligible for Resort Check In (assuming you are flying on a airline that participates in Resort Check In).
Since you only CONNECT in Chicago, and your final destination is not within the USA, you are not eligible for Resort Check In - regardless of the airline to which you are flying.
There are rumours some international travellers may be eligible for Resort Check In in the near future, but this is still speculative.