I'm usually not into this sort of thing but this guy pretty much nails it, less as an honest-to-goodness tour guide but more in the sense of "this is what living in Chicago is actually like for most people"...
...which is to say, Chicago is not exactly a very fun place to live! We have friends who we hold back from ever leaving because without them we'd be lost. And we have vices. In the summer it's a race to the nearest patch of greenery and patio seating; in the winter it's a race to the warmest/darkest bar. There are two weeks between each season where everyone falls in love with each other.