if you want something less touristy, i have always liked doing photo shoots under the El tracks, especially the brown line has some really cool dilapidated scaffolding type structures that look cool in photos.
i am also a huge fan of the graceland jewish cemetary at clark and irving park, just a few blocks north of wrigley field. it is a beautiful old cemetary with a lot of personality. in fact there are a whole bunch of cemetaries right along that strip to choose from…. i think because that used to be the far north side of the city and people got buried along the outskirts, but then the city just grew around it…
the music box theater on southport between grace and addison is beautiful, old-timey, with big red velvet curtains, an organist, and pinhole stars in the ceiling with projections of clouds moving across it…. bet you could get some cool photos there.
hope you have a good trip. if you’re looking for a good place to eat check out the crepe and coffee palace on clark between arlington and fullerton. it’s an algerian owned restaurant, the people who work there are really sweet, and their food is SO delicious. you can build your own crepe, they are the best i’ve ever had.