Gene & Georgetti - Chicago, IL

We decided on the oldest steakhouse in Chicago while looking for a nice piece of beef. Definitely the right call:

Longman & Eagle - Chicago, IL

Longman & Eagle is one of our new favorites, for a variety of reasons - great food (see the croque madame below), nice design, creative cocktails, and they have six killer rooms above the restaurant where you can stay for the night.