When travelling, the single most important thing to know is where to find the best bookstore. I’d like something with a great collection of non-fiction, preferably a privately-owned store-- something with character.
To me, the best souvineer is a huge sack of books. (A successful trip is when more luggage must be purchased to haul them back.)
The best bookshopping neighborhood in Chicago (and one of the best in the country) is probably Hyde Park on the south side. There’s a serious culture of books in that neighborhood, and while apparently it’s not quite as impressive as it used to be, there’s still some pretty cool stuff there. None of the bookstores are what I would call comfy-- no overstuffed chairs and lattes, but for sheer bookishness (towering shelves filled with obscure stuff), there are a couple of great shops.
I’d recommend walking along 57th Street. First stop would have to be Powells, at 57th and Harper (about 3 blocks west of the museum of science and industry). Mostly used books, but some new stuff as well. It was the original shop of the guy who went on to start the famous Powell’s in Portland. I think it’s now run by his father.
On the next block east, is O’Gara and Wilson’s. Also used books, but smaller and tends to focus more narrowly on history and a couple of other disciplines I can’t quite remember.
About 3 blocks down is 57th St. Books (corner of 57th and Kimbark). Probably the most traditional of the bookstores on this list, it has mostly fiction, but a good selection of popular non-fiction too, as well as a great childrens section.
Then, the corner of 58th and University is the Seminary Coop Bookstore, in the basement of the Chicago Theological Seminary. It doubles as another bookstore for the U of C and is bar none one of the best academic bookstores in the country. Non-fiction galore, and narrow, slightly claustrophobic shelves winding their way through the basement.
IMO, you can’t go wrong with any of those. When I was having a crappy day at school (and at the U of C there were a lot of those-- and we liked it!), I’d often find myself getting lost in one of those stores. And I mean, quite literally getting lost. Best of luck.
If you’re interested in used books… when I was in Chicago a few years back visting an ex, she took me to Myopic Bookstore, which was one of the best used bookstores I’ve ever been in, anywhere. I’m not familiar enough with Chicago to tell you where it is, but here’s the website.
Powell’s on Lincoln Avenue, north of Diversey get’s my vote. Huge store with used and new/remaindered books, and a room devoted to valuable collectables and antiques.
Myopic is a good store too, though not as extensive as Powell’s.
I’m still saddened by the demise of Stars Our Destination (I know, they’re still around virtually, but I prefer a store I can walk into and browse.)
If you’re into bizarre alternative fiction and comics, both mainstream and independent, check out Quimby’s on North Avenue in Wicker Park and Chicago Comics on Clark Street north of Belmont.