Can't tell you anything about the route from Chicago as we came in around Lake Superior, but the wife and I spent about 5 days there last summer. We did think the side trip to Niagara Falls was great and worth the time. We also spent a day doing the CN tower...not as worth it unless you're into 'saying you did', but really enjoyed walking around Chinatown and some of the nearby artsy areas. We started around Bloor and/or Yonge streets right downtown.
Have you gone around Lake Superior...maybe that's a dumb question if all the bikers in Chicago do that first chance they get?
Enjoy!!...and let me know if you want greater detail.