For a great steak place that has been around in Chicago for decades, try Gene and Georgetti's
http://www.diningchicago.com/restaur...ti/index2.html
rude waitstaff, but great steaks.
Gibson's is very good
For a chain I really like Smith and Wolensky's steakhouse. Nice views on the Chicago river and delicious sides.
Tried the NY transplant the Palm in the Swisshotel. Was not thrilled. Another miss IMO, is the Chicago Chop house.
I'm not really a fan of Italian food, but if I'm going to eat Italian, I usually head down to some restaurant on 18th street