Chicago is to Great Lakes cities what New York is to Eastern Cities in that it has Great Lakes architecture, but it's so densely populated, it can feel a bit claustrophobic at times, especially towards the Lakefront. Spacious and crowded at the same time. I'm pretty sure that Chicago has the most 3-4 story buildings in the country out of any city not New York.
I find huge parts of Boston and DC to be similar to Chicago, in terms of 3-4 story buildings and the way the landscaping defines the urban environment as much as the buildings. Chicago is very planned, you won't find power lines anywhere on the sidewalk for example. Also, Chicago uses a lot of sidewalk space for patches of grass and trees + the gangways.
A block of apartments in Brooklyn.
https://goo.gl/maps/qzoYsJFtnEr
Chicago apartment block.
https://goo.gl/maps/MXyB2mZAEas
Toronto is the only other Great Lakes city where the urbanity envelops the environment, giving it that big crowded city feel, but for different reasons. I think had Detroit continued to grow, it would have been similar in spots, but while Chicago streets are wide compared to the East Coast, Detroit streets are even wider.