I've never been to Chicago, couldn't tell you what a real Italian beef sandwich from there tastes like... Now I can tell you that the beef sandwich from Windy City is one of my favorite sandwiches I've eaten... I get mine wet with the medium gardinier(sp) and mozzarella... Such a great flavor combo!! The bread does get soggy, but that doesn't bother me one bit. Just makes you eat it faster. The service is top notch, the staff is always super friendly... Overall I highly recommend Windy City and will continue trying new things from there each visit... Did I mention they have frozen cheesecake on a stick??!!