I've been in Chicago since 97 and have been happy - a lot of people actually live downtown among the tall buildings so it's not completely deserted like some cities are - but there are tons of neighborhoods surrounding the city with beautiful tree-lined streets etc - as I said, I like it
Public transportation has its usual stupidity, but mostly works, home prices are going down, and you can look up places to rent in the Chicago Reader (best source of rental listings). I pretty much lived my first 3 years not having to drive anywhere and not really having to go very far for anything I needed.
As to a couch - I have to apologize - the hubby does not easily trust "people on the internet" so I have a feeling that would not fly