Don't get me wrong, there are plenty of Baaaaad Neighborhoods, but there are plenty of really nice places to live.
One rule I will never break, I will never ever live in a city that does NOT have alleys, i.e. Boston or NYC.
For those that plan on visiting Chicago proper, a very good restaurant is North Pond. It now has one Michelin star. It is located in Lincoln Park on the North Pond, so the view is beautiful and the food is quite good. The architecture is Prairie Style. There is valet parking. Sunday Brunch is a good deal if you are used to big city prices.
http://www.northpondrestaurant.com/
http://www.tripadvisor.com/Restaurant_Review-g35805-d455982-Reviews-North_Pond-Chicago_Illinois.html
In any case, I used to live a "couple thousand feet south" of where this photo was taken. Had to move because I couldn't afford the rent anymore.