Originally Posted by
YOWgary
Unless it's a situation like a huge, predicted-days-in-advance winter storm, it's pretty unlikely to see AC announce enough of a delay on an ORD-YYZ - in advance - that they're willing to re-ticket a non-status passenger on a Basic fare, before their first flight was even scheduled to depart.
...the strategy of arriving early enough to try and hop one of the earlier ORD-YYZ legs is definitely worth trying, though again, unless they're trying to get people moved in advance of incoming weather, that Basic fare may prove to be the stumbling block.
You're coming at this from the classic AC paradigm of not posting delays even when upline issues from before are guaranteed to create a delay. It's now quite common for AC to post delays well ahead, when the circumstances are known. My YYC-YVR the other day had a 1-hour delay posted 5-6 hours ahead, and on another recent day, most of the day's YYC-YVRs had delays posted early in the morning.
There are obviously still plenty of delays that crop up last-minute, e.g. a maintenance issue on the inbound YYZ-ORD, but the chances of a delay that will mess up OP's connection being posted early enough that there are options to deal with it are significantly higher than they were a few years ago. And once the connection is jeopardized, the Basic fare doesn't really matter.