The risks being as stated, the Maple Leaf seems not to suffer border delays to the same degree as the Adirondack. Per the information at Amtrak Train Status History, the average delay over the past month is 10 minutes late into Toronto.
Indeed, I'd contact VIA and let them know what your intentions are. What they say may or may not weigh in on your decision, especially the part about what your options/penalties would be IF the connection was missed for some reason. To be honest, two hours is on the edge of close IMHO, but not so close as to make me swear off trying it entirely. I think you have as much chance as making it as you do with connecting between any of the LD's in Chicago these days, and perhaps even better odds at that.
YMMV!