Originally Posted by silverbear
I would think that both of those cities would be difficult to enter or leave on a motor bicycle. Super highways and such.
Use Google Maps, they have directions for bicycles, which should be accurate enough for these purposes. As far as coming into Chicago from the southeast, there's a ton of surface roads that are safe enough for cycling. Getting out of DC will probably be a bit trickier, but the big obstacle will be getting over the mountains. You won't be able to ride the interstate through any tunnels; you'll be on state roads climbing up and down. It'll be beautiful, but a hard slog.
I think a friction drive would be less troublesome than gears and chains and jackshafts, and easier to work on when/if you have a breakdown, but bring a bunch of extra tires and an extra roller or two.