Chicago is my kind of town. OK, those are the lyrics to a Frank Sinatra song, but it still fits. Its nicknames are the Second City and Windy City; I like to call it New York Light. It has history and attitude like New York, just on a smaller scale. While it may not have as much to offer the novice tourist as the Big Apple, Chicago should not play a back-up role to its more media-centric sister to the east. It has a little something for all types of travelers: sports, culture, food, theatre, architecture, outdoor entertainment, and Oprah. What more could you ask?

Chicago