When I lived in the Windy City, if I had to impress someone, I always took them to Gibson's Steakhouse. The restaurant is located on trendy Rush street. The atmosphere is great, and the food is second to none. You pay a high price, but its worth it if you are into the very best. When you order your food they do the usual trick of bringing out raw wrapped versions of all of their steak cuts so you can seewhat you are ordering. They have a huge selection of sides, and give you everything you would want from a Steak House. Their may be a wait, but you can always hang out at the bar or go a few doors down to one of the Rush street hangouts.