Matt Nover, of the wonderful PaleoFuture blog, created this superb visual history of some of the better known predictions of transportation technologies and infrastructure for the Wall Street Journal.
For a book filled with these wonderful predictions, some of which are really close to reality, and other that miss the boat entirely, read Gregory Benford’s The Wonderful Future That Never Was: Flying Cars, Mail Delivery by Parachute, and Other Predictions from the Past (Popular Mechanics)