Chicago:
Not bad they try very hard to promote bike commuting and have bike laned streets that go almost anywhere you need to go. There is also a pretty good population of bicycle commuters, including myself. At the very least all these efforts make it clear that cyclists have a right to be on the roads.
It would be nicer is Trucks and JAM's didn't drive and double park in the bike lanes. Also the wintertime weather makes it more difficult, especially if you absolutely hate the cold like me. Also some of the suburbs are a challenge.