Well, I made a photography book for my mom for mother's day, and because I had a single person as my target audience (one who's taste in photography and the city I know very well) it was quite easy to choose images from ones that I had already taken. I didn't do any chapters, just compiled a book on qoop.com with 60 photos, one per page, in an order of my making. Since photographs on facing pages obviously are viewed back-to-back and side-by-side, I paid special attention to creating enjoyable comparisons/contrasts between the two, but as far as progression from one pair of facing shots to another, I didn't bother creating anything special/logical/thematic/what-have-you.
If I were serious about selling a book of my photographs to anyone out there, as it sounds like you possibly are, I would think about it much differently. The first fact I would take into consideration would be that there are A LOT of photographic books about Chicago. So, with this in mind, I would think about working on some kind of niche or particular angle I could take on this vast city of seemingly limitless photographic possibilities.
In order to produce the most attractive product, I would take an angle on Chicago photography that played to my strengths. From there, it might be distinguished and precise enough to warrant compiling an entire book on whatever photographs that that strength tends to produce (e.g., if I happened to take very good portraits of Chicago citizens, I would consider producing a book of just portraiture). If I had a large variety of shots (setting, theme, angle, style, whatever) that I considered to be of high-caliber and definitely wanted to include in a book together, I would consider working around a general theme or mood if the former approach proved too limiting. This could run the gamut from style, subject matter, location, etc. Of course, one could just go all-out and include a shitload of photos that they think are really good and just randomize it, but this might not prove distinctive enough. On the other hand, perhaps what prospective purchasers of photography books are looking for is an eye-catching cover with solid photographs in general, so it could be totally unnecessary to fret over the content so analytically and exhaustively. I would personally vet all of the possible formats and methods of production just to satisfy myself first, then think about what might sell too.
So as is apparent from the above rambling, I suppose I'm not entirely sure what I would do if I were producing a book. Personally, I would try to go with something more provocative or symbolic, like showing a lot of Chicago's forgotten/abandoned/ruined areas as emblematic of what implications contemporary lifestyle choices have on our nation's historic urban centers. This is really only because a lot of my best shots are centered around that concept, and also because the content of my shots needs to weigh more heavily on the aesthetic than the technical aspects of the photographs because I have an old P&S that doesn't measure up to a professional-quality DSLR in terms of clarity, focal flexibility, color, etc.
Yeah that wasn't very helpful, but I threw a few ideas out there I guess. Good luck!
If I were serious about selling a book of my photographs to anyone out there, as it sounds like you possibly are, I would think about it much differently. The first fact I would take into consideration would be that there are A LOT of photographic books about Chicago. So, with this in mind, I would think about working on some kind of niche or particular angle I could take on this vast city of seemingly limitless photographic possibilities.
In order to produce the most attractive product, I would take an angle on Chicago photography that played to my strengths. From there, it might be distinguished and precise enough to warrant compiling an entire book on whatever photographs that that strength tends to produce (e.g., if I happened to take very good portraits of Chicago citizens, I would consider producing a book of just portraiture). If I had a large variety of shots (setting, theme, angle, style, whatever) that I considered to be of high-caliber and definitely wanted to include in a book together, I would consider working around a general theme or mood if the former approach proved too limiting. This could run the gamut from style, subject matter, location, etc. Of course, one could just go all-out and include a shitload of photos that they think are really good and just randomize it, but this might not prove distinctive enough. On the other hand, perhaps what prospective purchasers of photography books are looking for is an eye-catching cover with solid photographs in general, so it could be totally unnecessary to fret over the content so analytically and exhaustively. I would personally vet all of the possible formats and methods of production just to satisfy myself first, then think about what might sell too.
So as is apparent from the above rambling, I suppose I'm not entirely sure what I would do if I were producing a book. Personally, I would try to go with something more provocative or symbolic, like showing a lot of Chicago's forgotten/abandoned/ruined areas as emblematic of what implications contemporary lifestyle choices have on our nation's historic urban centers. This is really only because a lot of my best shots are centered around that concept, and also because the content of my shots needs to weigh more heavily on the aesthetic than the technical aspects of the photographs because I have an old P&S that doesn't measure up to a professional-quality DSLR in terms of clarity, focal flexibility, color, etc.
Yeah that wasn't very helpful, but I threw a few ideas out there I guess. Good luck!