If you want to explore them all, you're probably going to want a guide, and not one of those travel books that only takes you around the more heavily touristed areas. Fortunately, the publishers have provided. We now have The Chicago 77: A Community Area Handbook by Mary Zangs and the newly updated third edition of the venerable AIA Guide to Chicago, edited by Alice Sinkevitch and Laurie McGovern Petersen. Neither of these two books will tell you where to get a really good, cheap lunch or a beer (that's what your smartphone is for), but they will—one more than the other—provide a decent introduction to corners of the city you've never been before.
Of the two, the AIA Guide is by far the more informative, though its focus is fairly narrow: as befits a book produced by the American Institute of Architects, it's all about the buildings.
"The Guide," its editors write in their introduction, "is illustrative rather than encyclopedic, presenting a representative selection of buildings in addition to the essential landmarks." The blurbs themselves are strictly informative, resolutely impartial; authors leave it to the reader to draw his or her own conclusions about the character of a neighborhood. (Here's Sinkevitch in her introductory essay on Garfield Park and Austin: "The West Side shows typical inner-city scars of age and blight. . . . But the positive effects of dedicated institutions and strong individuals are seen in every neighborhood.")
But in describing the many kinds of buildings—office buildings, apartment buildings, private homes, schools, churches, parks, and random curiosities—and pointing out details not only about architectural features but also who built them and why and how they've been used over the years, the authors also obliquely tell the stories of different neighborhoods. The best way to use the book is, as the title implies, to take it along on a walk or a drive through some part of the city you've never been before and see what you can find.
Zangs doesn't provide too much substance, but some of the factoids she produces are interesting. Such as the reason houses in the older neighborhoods, like Pilsen and Lincoln Park, are below street level: the streets were raised in 1875 to accommodate a new sewage system. It's also kind of fun to learn who your neighborhood, and maybe your street, was named after—even though, it must be said, a lot of the backstories are not terribly interesting. The Chicago 77 concentrates far more on history than on describing what the neighborhoods are like today—it appears that Zangs did a lot of her research not out in the field, but in the library (and maybe even using earlier editions of the AIA Guide!)—but even the most trivial history becomes fascinating if it relates directly to where you live.