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.
THIS IS BY FAR THE BEST THING I HAVE EVER DONE. When I was there in September 2 years ago, we all did this, even the Chiacgo natives. You get history, you get to talk to the people you're hanging out with, it doesn't revolve around drinking or freezing or sweating, its perfect. Cannot recommend it enough.1) River tour. If it’s warm out, a historical/architecture tour of Chicago is rad for both tourists and locals. Aside from a nice, breezy trip on the not overly smelly river, architectural tours in Chicago actually have significance. This isn’t your chumpsville city where you paid a bunch of dipshits a cool million to design a glass dildo in the center of your three-block downtown. Buildings in Chicago actually mean something to the history of the city, and you’ll learn something about the meat packing industry, health and sanitation, immigrant migration, and other cool stuff that you probably won’t appreciate because you’re a fucking uneducated hick. Fuck you.
I too took an architectural boat-tour of Chicago and it was awesome, I also highly recommend it.
Yeah I can pretty much vouch for this, but it's missing the actually pretty good music scene. Head over to Reggie's or the Bottom Lounge when someone you've heard of vaguely but aren't sure what their music sounds like is playing, and you'll probably have a good time. And there's a bunch of house venue shows and DIY punk and stuff like that too. Just don't go to anything at Congress.
That is a fantastic read, and probably has an equivalent for every major city.