"Instead he took us on a nighttime tour of the city, behaving in part as though he were its sole proprietor and in part as if he were the guide on a Gray Line bus tour. Here we have the twin towers of Marina City, here we have the John Hancock Building, this is the Art Institue, this is the fabulous shopping district of Michigan Avenue....I had expected Chicago to be grimy and cramped, the summit of midwestern dreariness, with nineteenth-century red-brick buldings seven stories high and a population made up entirely of Polish, Hungarian, and Irish workmen in overalls. Whereas this was a city of braod avenues and glowing towers. The architecture was stunning; there was nothing in New York to equal it. Of course, we stayed close to the lake. Go five blocks inland, you'll see all the dreariness you want, Ned promised. The narrow strip of Chicago we saw was a wonderland. Timothy took us to dinner at a French restaurant, his favorite, opposite a curious monument of antiquity known as the Water Tower...." - Robert Silverberg, The Book of Skulls
I can mostly agree with that description. The twin towers of Marina City we used to call the Jetson buildings -- if you saw them, you'd know why. Alternatively named the corncobs. The view from the top of the John Hancock is gorgeous, though over-priced (ditto Sears Tower); I've always liked the elegant sweep of the building. The Art Institute is of course amazing, even for someone like me who knows far too little about art (I do like the layout of the Philadelphia Museum of Art better, and the British Museum has a lot more stuff (impossibly organized). Haven't been to the Met in so long that I can't properly compare).
The Michigan Avenue shopping district is indeed fabulous, though over-priced. For bargains, you're better off haunting the vintage clothing shops or wandering through the Near North Side. There's also a fair stretch of shops on State Street (which they were trying to improve, last I was there). The Water Tower is one of the few buildings that survived the great Chicago fire (I'm afraid I have no idea of the date), that supposedly was started when Mrs. O'Leary's cow knocked over a forgotten lantern in a barn. (The Tower survived because it was made of stone and filled with water, go figure. It should not be confused with Water Tower Place, the immense shopping mall next door). The Chicago fire did have one benefit -- when they rebuilt the city, they made some attempt to do it logically, rather than just letting it grow. So there's a gorgeous strip of parkland all along the lake where nobody can build, and the city is built on a grid (numbers one way, names the other), which makes it fairly easy to navigate. Would be easier if the names were in alphabetical order (or if they were both numbers, like New York, but I feel that method lacks soul).
You may want to check out a page from Justin's diary, which has some interesting info on Chicago. Be warned -- you may never come back here. :-) I find his stories fascinating.
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