I'm not a local. Been there twice. Things I did while there....visited Lincoln Zoo, Buckingham Fountain, Millenium Park (Cloud Gate), Shedd Aquarium, Adler Planetarium, nights shots from top of Hancock Building and Skydeck, walked across Wacker Drive and got some night shots over the canal, last but not least skyline shots from Adler Planetarium. Spent a lot on parking throughout the day. Saw some crazy drivers there. Good luck! Chicago was a lot of fun.