Seeking a bit of advice on a weekend trip to Chicago

[Monetto]

Hey Midwest forumers, I hope everything is going well. I'd like to ask for your advice regarding a weekend trip to Chicago, since a buddy of mine and I will be driving down this Friday afternoon and will stay until Monday. I'm an architecture student and we are both urban enthusiasts in general. I'd like to see both the touristy side of Chicago as well as the more real, down-to earth neighbourhoods.

I tend to like basic, unassuming neighbourhoods that have a good sense of place, layers of history and habitation, and a great urban vibe overall. For those of you familiar with Toronto, I like neighbourhoods like The Annex, Little Italy, West Queen West, Kennsington Market, etc.

So, basically, my question to you is, what are some of the major, must-see attractions of Chicago? Also, what is your favourite dive bar? Where's a good place to photograph some industrial grit? Finally, as I've not yet made reservations or any plans of accommodations, what's a good, reasonably cheap, reasonably central place to stay?

Thanks in advance and I appreciate your help and expertise. Cheers