I've thought about this too, maybe there is a train route you could follow on google maps. Switch from car to public transportation and follow the map. But even still, there is chance that it might run you into a bad part of town that your character would never be internally caught in, or maybe they casually go to a bar that is impossible actually to get into.

Character: "I was walking ______ street at 3am." Everyone that knows that street cringes. You could probably forget about having a NY Times best seller and they might remember you, tainting your future novels prospects.

The Devil is in the details, and if you don't know the city he's probably plotting against you.