Having spent a few years of my life living in Chicago (still my favorite US city), I am often asked for suggestions for restaurants and things to do, apart from the obvious. No deep dish suggestions here! Chicago is so much more than those lactose-laden pizza bombs.
Chicago is a city of neighborhoods and my personal favorites are: gold coast (I lived in the heart of the GC, so obviously it tops my list), river north, west loop, old town and lincoln park. While there is something magical about Chicago in the summer (where else can you be in one of the nations largest cities and walk 3 blocks to the “beach”), I really encourage friends to visit in the winter as well. To me, walking around Michigan Avenue at Christmastime, with a chill in the air and hot cocoa in your hand, is Chicago.