Hopefully you'll be together soon! Wishing the best for you.
I am in Seattle Washington. I actually met my husband online and then went to Toronto to meet him and visited him several times. I fell in love with Toronto-- love the city vibe. It is much easier for me to immigrate there, than him here, because we are both ethnically Iranian, the US freaks out about this. Even though I was born in the USA, he was born in Iran and I talked to a few US Immigration ppl and this would cause a huge delay. Ridiculous, he's been a Canadian citizen since the age of 2 ! Darn USA Immigration policy!
Chicago is a cool place, you're lucky and blessed with a nice subway!
Don't apply within! Takes way too long. Outside is much faster! Plus you can do all your things more quickly, like the fingerprints and the background check stuff. None the less, I think it is ridiculous how long it takes just for American and Canadian citizens who are married to live with one another.
I don't think I could ever lie to the customs officials. They kind of scare the crap out of me. Plus I don't really know anyone else in Toronto... so who would I say I'm staying with ? :-(
What are you thinking of doing in terms of work in Canada?
Best of luck!