Hey ABCTheNorth,
First off, congratulations on getting into two great programs. I'm a first year at SOM right now and can hopefully give a little perspective on that side of your conundrum.
You're correct that Yale is more of a consulting powerhouse than it is a finance school as you mentioned. That being said, that has much more to do with the interests of the students than the reputation of the school in my opinion. Going to consulting vs. finance events during the first semester is a drastic difference. More people just want to do consulting at Yale right now than finance. I pulled up the document of where the class of 2020 is going, however, and it's got every big name in the finance world you can think of on it. I'm sure Booth has all the exact same names. All the big names come recruit at SOM so its just about how you perform in your interviews and how you connect with the folk at those firms - you'll get your shot to impress.
As far as your main question you asked regarding brand recognition in Canada and the US - anecdotally, I've not once ever encountered an issue with Yale's brand recognition and none of my international classmates (including Canada) have either. I fully understand that SOM is not the same as the parent university, but its a top 10 MBA program with the Y-bomb in its name - the brand does just fine from my perspective.
For a finance person, you seem to be ignoring the elephant in the room regarding this decision. The perspective you will get from UChicago and Yale in your finance classes will be different. At Chicago you'll focus a lot on free markets and market efficiency with strong influence from people like Friedman and Fama, while at Yale you'll spend a little more time looking into behavioral finance and market failures with influence from people like Shiller and Chanos. Obviously both schools will cover everything you'll need to know about the finance basics, but when it comes to electives for a finance focused student, the difference in these programs is large. Which topics would you prefer to spend more time thinking about? It's just personal preference.
50% scholarship or around $75k is nothing to take lightly, but you really can't go wrong either way. If you want to chat more about SOM just PM me - one of my good friends is actually going to an infrastructure investment fund this summer (sounds like a really cool industry) and I can connect you two if you want.
Good luck with the decision and congrats again!