Flight from ORD to YOW will be on a regional. If AC prob no J anyway. The flight is all of an hour and fifteen in the air. I would protect the 330 portion and not care about the Connector. I am not sure coming in the day before is worth it, unless you want to play tourist, in which case Ottawa can be a nice place if you have not visited before. I would not bother with a double connect, if I did not really have to.