Lake Shore to Syracuse, then Maple Leaf to Toronto would be the simplest.
The other option, less desirable, would be to connect to the Wolverine and get to Detroit at 1 am, spend the night there or Windsor, then take VIA the next day from Windsor to Toronto.
1)Wolverine to Detroit/transfer on your nickel to Windsor/catch a VIA Train to Toronto.(since the Canadian only runs three days a week and IF the SWC is on time in to CHI, you could spend the night in Windsor,catch the morning VIA Train to Toronto-if the SWC is late you could spernd the night in CHI, catch the early morning Wolverine to Detroit/late VIA train to Toronto from Windsor where you may make your connection to the Canadian if on time, or you may have to spend a night in Toronto depending on the schedule/time keeping!)
2)Lake Shore Limited to Buffalo, then the Maple Leaf to Toronto, if you wanted to make the connection that same night you could ride the Bus from Buffalo to Toronto, otherwise the connection is too tight in Toronto to ensure you make the Canadian the same night but theoretically it's possible but I wouldn't risk this, next Train is in two days!)!
Ive done both, I prefer the Lakeshore/Maple Leaf connection in Buffalo,it's also the least hassle! (you could also go on to Rochester, less time to kill but Rochester isnt as interesting as Buffalo to kill time between Trains)but I have a Free place to sleep in toronto since I have friends and family there, hotels can be pricey in Toronto if you dont plan ahead!