In Chicago, there are plenty of good steak houses. There are others that are more expensive, more popular, fancier, and more well-known. But if you are looking for a comfortable, classy but not ostentatious steak house serving good quality food in a convenient location, Kinzie Chophouse is a good choice. Located across the street from the Merchandise Mart, the only real drawback to Kinzie is the uneven quality of its servers.
For those who eat fish and chicken and not beef, the shrimp risotto is excellent, as is the chicken pot pie. Kinzie also has good salads and a decent key lime pie.
For a cheap date, check out the super cheap appetizers in the bar during happy hour.
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