Another site worth checking out: Google Maps Flight Simulator
I just happened upon this flight simulator for Google Maps called Goggles, and though it is short on features, it is absolutely worth checking out whenever you have a moment. All you do is select a starting point and control yourself using the keyboard arrows. There is a limited selection of locations, but the site offers directions on how you can link your hometown to the project. I wish such a feature was available in Google Earth so you could fly between the 3D buildings and have other people that you could have dog fights with, but I can only imagine how much time I would waste playing with such a toy. Chicago isn't linked here yet, but as soon as I have a minute I will put it up. Hope you enjoy.