The most walkable neighborhoods in Chitown you ask? Why they're The Loop, Near North Side and beautiful Lincoln Park. For those who like to do a walk-about in the city of big shoulders, check out City Walks: Chicago: 50 Adventures On Foot The deck is also available at Climate Home - 2462 N. Clark, 1971 N. Fremont or 1702 N. Damen.
Even for the born and bred Chicagoan, this deck of cards has recommended city walks in 50 neighborhoods throughout the city. I suggest them for dog walkers too.

The cards provide the route in a map format - the flip-side provides points of interest and historical information regarding the area - honestly, one of the best investments for learning more about the Windy City