San Francisco, CA, New York, NY, Boston, MA, and Chicago, IL are rated by walkscore.com as some of the most walkable cities in America. A city center, enough people, and complete streets are some traits of these walk-friendly cities.
Specifically, the top five walking cities are 1) San Franciso, CA, 2) Boston, MA (I have family there, and I agree.), 3) New York, NY, 4)Philadelphia, PA, and 5) Chicago, IL. However, this is not to say that these are your only options, since there are a lot of fine bike and walking trails all over the US.
I hope this helped!
I lived in Chicago and I can tell you that is VERY walking friendly. One thing that makes this city so walking friendly is how centrally located everything is. Almost everything in the entire city takes place either Downtown or Lincoln Park. Also the city is built like a gridlock. almost every street runs either perfectly horizontal or vertical, which makes navigation extremely easy.
So everything is in close proximity, and it is VERY hard to get lost.
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