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I know you said not too accurate, but I am confused why people are adding New York+LA+San Fran??? Have some of these people been to Chicago?
Realistically, any combination of Philadelphia+Boston+DC+Detroit is the best. (not all 4 at once, but those 4 cities). I would also throw in a little Manhattan and Queens.
Detroit has the industrial, midwestern feel that is a tick smaller than Chicago.
New York has the oversized skyline, pure size, and grittiness of Chicago.
Boston has the ritziness and sophistication and similar density of Chicago outside the core.
There's a white collar part of the city that's booming and gentrifying, and often quite pretty. There's an industrial legacy that still exists after taking a beating with parts of the industrial areas going through a construction boom from being repurposed as mixed-use districts. There's a massive lakefront, but unlike Cleveland, much more of it is being used for recreation as in SF and parts of Detroit. University Circle and Hyde Park and their surrounding areas are an island of sorts centered around academics and medicine in a rougher part of town.
Hard to narrow it to 3: I see aspects of NYC, Philly, Detroit, Milwaukee, and Toronto.
It kind of depends on what part of Chicago you are in.
The South and Southwest sides, and parts of the West side definitely have much more of a Midwest feel.
The Downtown Core and North Side- have more of a Northeastern feel.
Just minus the skyline and lakefront. Chicago also is not a row-home city in the general sense of what we call row-homes as in whole blocks of attached housing that are similar. That is why a Toronto or NYC Manhattan is needed in the mix IMO. Toronto brings in the tallness and lakefront setting of course and neighborhoods of SFH's with front greens-space. Detroit is brought in as merely to include industrial decline and hoods of course. Though most US cities all have hoods.
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