I'm not going to either, but if I were to go, I would try to attend the Canadian one. I can't help but believe, however, that the Chicago con will decrease the attendance in Toronto, simply out of convenience for many folks
This year I am trying to make the Chicago one. Due to the timing and available finances, Toronto just isn't going to work for me. There is still an outside chance I can make it to Chicago. Not sure of the pros/cons of having two TFcons are. The general feeling I get from conversations I see on Twitter is Toronto will always be the main TFcon, while the US one being secondary. Time will tell if this is true.
They might intend to have Toronto as the main one, but I could see it dying off if Chicago is yearly as well. (not fatalistic, just one simple fact: cheaper travel)
I'm 100% in for Chicago for two reasons. Never been to Chicago, and I have a couple friends going, who I'd be traveling with. Toronto is up in the air for me, as I got invited to another convention that weekend.
Toronto, I'd been planning on it before I knew about Chicago, which I have a schedule conflict for anyway.
Chicago. I could almost go to TFCon in canada, but I have gone to Botcon the past few years and its my major expense for a vacation. TFCon CHicago will be very close and I can drive to it, plus I have relatives there though we havent visited many of them lately, except for my Dads cousin, and its always been a good place to go to visit. also the CHicago one is in what October , the end of it, so Ill have more income then to be able to go to it.
If things work out, Chicago. Only because of travel, and the time of the year. Wishing I could do both. But the big downside... No water slide.