After a bit more searching, this time online, we discovered its identification. It turns out the ID books I was using (both photographic and artistic renditions) just do a poor job of showing all of the proper colours for this butterfly.
As one of the larger skippers in its family, this particular species has a wider range further south in the US but is fairly common in Southern Ontario - typically not found north of the Great Lakes though. It utilizes various legumes as host plants, which means they aren't really specialists and therefore fairly widespread. As this photo demonstrates, they have a preference for flowers that are blue, pink, red, purple, or white-coloured but tend to avoid flowers that are yellow.
Now that I've seen one I'm sure I'll start seeing them everywhere! There's something to be said for being out there on your own trying to identify species (whether they are birds, insects, etc.) - often these kinds of self-learning adventures help the identification of the species stay in your memory better than when someone finds them and identifies them for you.