Originally Posted by
EricTheNerd
As for Chicago, I think one of the main draws has to be architecture, there are quite a few interesting buildings in the city, and Frank Lloyd Wright is from Oak Park (a leafy suburb). As a major city, it also has a variety of museums. It's also somewhat of a hipster paradise, at least according to my hipster friends who moved there in droves after college. If you're interested in fancy food, Alinea is the best restaurant in the country (according to "The San Pellegrino World's 50 Best Restaurants" rating).
I just want to throw in a second positive vote for Oak Park - really great to walk around and see all the FLW homes and the Unity Temple is absolutely incredible.
If you like architecture, there is a boat tour that leaves from right by the Wrigley Building off of Michigan Avenue. It was really well done and I enjoyed it tremendously (make sure you're getting on the architecture tour).
And the Art Institute is one of the great art museums in the world. The Chicago Symphony Orchestra is also astounding at Symphony Hall.