River North.
Wrigleyville.
Toronto sports culture is also severly lacking.
I'm curious to find out what you found interesting about those areas. I walked around the Wriglyville area and found it to be just like walking around the east end of the Danforth. (minus the stadium) The only street I saw that had any life, was N. Clark St. but maybe I missed the cool area, so fill me in. I'm not a sports fan, so I can't relate to the sports culture.
What would you say is the most interesting part of both River North and Wringlyville (what streets specifically) and what is it that made them interesting for you? I've seen a lot of Chicago but obviously, there are probably many interesting things I missed and need to see next time I go.
River North was interesting to me, only for the architecture. (and the infrastructure) Other then the cool skyscrapers and bridges, what makes this area interesting? After 6/7pm, this area was completely deserted, when I was there. (south side of the river) Where are the unexpected surprises or just something out of the ordinary?
If I were to pick a Chicago area that was a little different and interesting, I would say Printer's Row, for the large, historic warehouses and buildings. It's still a bit quiet but it has good potential to become a tourist area. I find much of downtown/north Chicago to be lacking in pedestrian traffic, especially when the sun goes down. The only lively part of Chicago I saw, was the strip of Michigan Avenue, from around Buckingham Fountain, north to Lakeshore. (the Magnificent Mile) Streets like Rush, Clark and Lincoln had pedestrians but they were still lacking the vitality other big cities have.
Over-all, I just find much of Chicago to be ordinary and lacking any distinctive character. (especially lacking in pedestrian vitality, when compared to Montreal or Toronto)