I lived in Chicago for a couple of years. Still have family there and visit at least once a year:
If you dont have a car, chicago has free trams for the tourist areas in downtown. Not sure if it runs off-season. If the weather is not too cold, rent a bike. You can ride around most places near the lake and get plenty of pictures. Public transportation is also there. Not as good as NYC.
# Adler Planetarium: best view of the Chicago Skyline.
# Take a picture of the 'Bean' in Millenium Park
# Navy Pier is somewhat over-rated, but worth a visit. But if you go along the bike route, you will see some nice places to shoot pics.
# The Architectural Tour is a definite must. Take the BOAT tour NOT the bus. You get much better views. Take a wide angle lens...A fish eye might be real fun. I was not into taking pics when I went on the trip a while back. Someday...
# John Hancock building: supposed to have better views than Sears Tower. However, the only time I went up there it was so hazy it wasnt worth it.
# Michigan Ave: walk up and down this street. Plenty of people. You can get plenty of street photography here.
# Playboy mansion: apparently the first playboy mansion was in Chicago...In any case, the building is not much to shoot. But if you go to that area, there are a lot of nice houses, stonework etc.
Stay away from: Chicago is a pretty safe in the downtown area. If you are not a winter weather guy, It can get really cold when the wind blows near the lake areas, which is pretty much the downtown. I always have to have gloves and something to cover my ears in additon to everything else...
Have fun!
Some pics:
The bean
Last edited by psychdoc; 11-14-2015 at 03:36 PM.