Doubt any single such document exists, and you would have to pick a date. There are numerous 'old city map' sites on line which have out of copyright maps of particular cities.

On the accuracy topic, I question the 'trolley' label for either the North Shore or South Shore. And, FWIW, Red Atlas Book(.com) and the treeware book itself reproduce Soviet maps of several US Cities. In the Chicago case, having lived there, I find the map full of mistakes as to railways.