Chicago, Illinois

America's "second city" is where my parents met and one of my favorite places to visit in the Midwest. While Wrigley Field is one of the best places in the country to watch a baseball game and the shopping along Michigan Avenue rivals any collection of stores west of NYC, if you only have time to do one thing in Chicago then you should take the architectural boat tour. The diverse collection of office and residential buildings varies greatly in dates and styles, reflecting the history of the city.