Indeed, thanks for the welcome to MobileRead and in return welcome to Chicago.
The additional info and clarifications helped considerably in improving my understanding what is fact and what is funny in the post thus far. Some things just don't interpret well without exposure. And then there is spatula humor.
If you care enough to give them the very best, give them a spatula.
Anyhow, it good to discover that your residential placement is out of necessity not naivety. In that case, I actually envy you. It would be nice to just be able to walk a few blocks of so to meet with clients. Instead its the daily commute to the office- Fortunately I am better off then most since I work rather flexible hours and thus rarely, if ever, am in transit during the dreaded urban rush hour.
The horror.
I noticed that you sketch and doodle. It was sketching and doodling that brought me to MobileRead. Well not the act of so much as the want for something to use as a digital sketch book. I had hopes that one of these newfangled eInk devices with the Wacom stylus could be used for drawing. Alas, not so much- Yet. the point is, if you are interested in drawing, particularly life drawing you might be interested in the following artist groups / social activities:
The Chicago Palette and Chisel
http://www.paletteandchisel.org/
Dr Sketchy's Anti-Art School (Chicago)
http://en.wikipedia.org/wiki/Dr_Sketchy's_Anti-Art_School
http://www.myspace.com/drsketchyschicago
The Brimstone Drawing Club
http://brimstonedrawingclub.blogspot.com/
http://www.myspace.com/brimstonedrawingclub
The first will probably appeal to the culture in you, the other two the vulture. Actually they are all pretty classy and well run organizations even if the later are less then conventional.
For the reader in you, something conventional but unfortunately only annual so mark it on your calendar. Every spring, either the first or second weekend of June be ready for the best street fair in town, Chicago Tribune Printers Row Book Fair, located in the south loop at Dearborn and Polk. Blocks and blocks of books new and old. A little taste of literary heaven.
Until then, I'm game for joining your MobileRead MeetUp. Not sure what I have to offer it since I don't own a mobile reading device and the only real knowledge I have of them I have gleamed from here. Still, if more is the merrier then more it shall be.
Oh, and I second the vote for the Watertower location- But suggest the Boarders Cafe across the street from the mall to be the actual rendezvous spot.