I don't get to travel much, so when I do, I am usually amazed by just about anywhere. Still, the greatest place I've ever visited was Chicago. Aside from brief forays in Cincinnati on the way to the interstate, I have never actually traveled to a major city.
I have so many wonderful memories attached to Chicago, due mostly to the Star Trek convention I was attending there. Meeting celebrities, making new friends, trying out the local cuisine (Giordanos FTW!), dancing, drinking, and just being in one of the greatest places in the U.S.
Finally, being in my hotel room, standing in front of the wide plate glass window at dusk, and staring at the Chicago skyline. For a boy who comes from a town of 8,000 people, it was sublime. It was freedom. I'll never forget it.