I was just in Anchorage with my bike. Now THERE'S some untapped territory. The "city" (an outpost, really) is totally flat until you butt up against the mtns, has a nice wide grid system of roads, a big cycling scene, a few shops (hey an REI!!), miles and miles of bike trails, MOOSE, not much traffic, you get dizzy on all the daylight, and hipsters get run out of town. And in the winter, hook yourself up with some spiked tires, woolen knickers, and you're all set. Can't possibly be worse than Chicago in the winter.