I wanted more urban shots, and we took ours on LaSalle street in the financial district, in front of the CBOT, in the streets, by the el, etc. I personally loved the shots. That's not technically north side, so you can also check out Lincoln Park, it's very green and colors of leaves, etc. will be beautiful in Oct. Ask your photog about behind the Chicago History Museum and/or in front of the Planetarium.
Lincoln Square has some cool places. The fountain should be working now. There are gateways to the actual square area that might be cool. Logan Square has a really cool boulevard with wide grassy areas separating the two sides of the street- around Kedzie and Logan Blvd- very cool place- almost European style.