Originally Posted by Seven999
In Chicago, the roads are what'd I'd say are decent... bike paths are paved, so I wouldn't do much or any dirt paths or gravel or worse, really. The roads in some areas have a small bike lane.
Chicago is fairly flat, almost no hills. (generally true for all Illinois/midwest).
If it were me I would get a single speed or fixed gear road bike. I did a search on craigs list chicago and got a TON of hits. there ya go