The dotted red line on your map is a route built as the Pullman Railway by the Pullman Company, which built streetcars as well as its well-known railroad cars. The Pullman Railway was a demonstration line for its streetcars as well as a transportation facility. It later became part of the Calumet Electric.
The cable connection shown in green on your map
is just one of about a dozen cable car lines in Chicago, a technology which
is certainly better known at San Francisco. The elevated railroad
route on the map was originally (in 1893) powered by small steam locomotives.
It's still operated today by the Chicago Transit Authority--by electricity,
of course.
All in all, your map is a splendid piece of history!