The Dearborn is an easy-to-like spot in the Loop with a well-rounded American menu that works for a lot of occasions. It’s nice enough for a business dinner, but still casual enough for lunch after that Segway tour you took with your parents. Plus, the space is huge, with multiple rooms that work for large groups or couples on a date. Order the pork belly appetizer and any of the salads, then make sure someone gets a cheeseburger—it’s really good.