Um. I live here, in the city, not the burbs. Chicago IS depressing. It has the worst traffic of any city I've worked in. That includes SF (Silicon Valley), Boston, and Washington DC. Outside the US I've lived near Frankfurt and in Paris.

Those "efficient" looking gridded streets have a traffic light every 200 feet. In uptown Chicago it can take 30 minutes to drive 6 miles to the nearest Costco. The freeways feel like they haven't been updated since the 50's, and the only ones that move are toll roads. What Chicago really needs is much better, faster public transit (like Hong Kong or Paris) that moves between the city and suburbs. The L with 20mph trains and tracks that date back to the early 20th century isn't cutting it.

In terms of depressing... the grid pattern does make everything look monotonous, and the architecture is largely the same (block apartments and tenements from the 1900's-1920's. But I'd say the depression is due more to the general shittyness of big US cities, i.e. homeless people picking through your trash on a daily basis. Chicago looks great from the air, it has a gorgeous skyline, and by US standards it's pretty good (i.e. not Detroit). But that's not saying much. We often refer to our new hometown as "Shitcago".

My impression is that most people who think Chicago is the greatest place on earth either don't live downtown (and don't visit it enough to know it), are pathetic sports fanboys who live in cubicles or in the burbs for most of their lives, or simply haven't lived anywhere else that's better. The best place I've lived in the USA, hands down, is Salt Lake City. I say this as a liberal atheist who is about as non-Utah as you can get. The grid system is on a much larger scale than in Chicago, and it really works. Of course, greater Salt Lake is ~1/10th the population of Chicago.