Not that I dislike Chicago, but I absolutely LOVE Toronto even more. The people are insanely friendly, the city is very clean, you feel very safe.
If you fly into Billy Bishop airport you can literally walk to Rogers Centre. The CN Tower is right next to the stadium and has breathtaking views. If you are a hockey fan the Hockey Hall of Fame is nearby as well. If you want to fork over the money you can stay in the Marriott which has rooms with field views.