Have to agree. Running in the city is pretty poor. The lakefront is totally packed on the weekends so you are dodging fate people walking and on bikes all day. If you ride a bike, how can you think it is okay to fly through people going 20 MPG on the lakefront path. Don't even get me started on the roller bladers either.
Running on the side streets is the only alternative. Use the one ways. You will get killed by a car coming out of the alley if you are on the sidewalk.
Good advice to go up to the burbs for some running. The further you go North and West means you can actually get some rolling hills too.
Sadly, NYC and Philly have a much better running scene. I wish it were not so, but it is true.
I love Chicago, as I was born and raised here, but it is abysmal for running compared to about any other city. I would not mind moving either to be honest if that is your next point...