Of the cities I have visited around the globe, the one I like most is Chicago. It has its share of everything (as most cities do) – tall buildings, famous landmarks, historical sites, museums, shopping districts, theatre, playing fields, zoos, parks - and an awesome lakefront setting (not common fare in most other cities). The best part is the fact that the metropolis is not squeezed into a tight spot (say, like Manhattan Island) but is spread out. When you walk between the buildings, the space between them allows you to appreciate how majestic and tall these structures really are; imposing feats of architecture as dreamed of by their designers.
Ironically, the best view of the entire city is not from Sears Tower, the tallest building, but from the observation deck of the John Hancock Building on the north-side of the city. Not only do you get to see the cityscape but you also get some nice views over Lake Michigan. I was fortunate to go there on a gloriously sunny day as the pictures will attest.